cas 17435-72-2, Ethyl 2-(bromomethyl)acrylate

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A new end group structure of poly(ethylene glycol) for hydrolysis-resistant biomaterials
A new PEG end-group structure (α-PEG-MA) was designed and synthesized. When compared with the conventionally used PEG-acrylate structure, the vinyl group in the new structure showed comparable reactivity in thiol-ene reactions, but the formed materials were hydrolysis resistant because there is no ester linkage in the backbone chains. Copyright
Tong, Xinming,Lai, Jingjing,Guo, Bao-Hua,Huang, Yanbin
p. 1513 - 1516
(2011)
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Design, synthesis and evaluation of [3H]PF-7191, a highly specific nociceptin opioid peptide (NOP) receptor radiotracer for in vivo receptor occupancy (RO) studies
Herein we report the identification of (+)-N-(2-((1H-pyrazol-1-yl)methyl)-3-((1R,3r,5S)-6′-fluoro-8-azaspiro[bicyclo[3.2.1]octane-3,1′-isochroman]-8-yl)propyl)-N-[3H]-methylacetamide {[3H]PF-7191 [(+)-11]} as a promising radiotracer for the nociceptin opioid peptide (NOP) receptor. (+)-11 demonstrated high NOP binding affinity (Ki = 0.1 nM), excellent selectivity over other opioid receptors (>1000×) and good brain permeability in rats (Cb,u/Cp,u = 0.29). Subsequent characterization of [3H](+)-11 showed a high level of specific binding and a brain bio-distribution pattern consistent with known NOP receptor expression. Furthermore, the in vivo brain binding of [3H](+)-11 in rats was inhibited by a selective NOP receptor antagonist in a dose-responsive manner. This overall favorable profile indicated that [3H](+)-11 is a robust radiotracer for pre-clinical in vivo receptor occupancy (RO) measurements and a possible substrate for carbon-11 labeling for positron emission tomography (PET) imaging in higher species.
Zhang, Lei,Drummond, Elena,Brodney, Michael A.,Cianfrogna, Julie,Drozda, Susan E.,Grimwood, Sarah,Vanase-Frawley, Michelle A.,Villalobos, Anabella
p. 5219 - 5223
(2014)
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Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines
A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.
He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng
(2021/05/31)

Copper-Catalyzed Intermolecular Alkynylation and Allylation of Unactivated C(sp3)-H Bonds via Hydrogen Atom Transfer
We describe Cu-catalyzed intermolecular alkynylation and allylation of unactivated C(sp3)-H bonds with singly occupied molecular orbital-philes (SOMO-philes) via hydrogen atom transfer (HAT). Employing N-fluoro-sulfonamide as a HAT reagent, a set of subst
Liang, Lei,Guo, Ge,Li, Chen,Wang, Song-Lin,Wang, Yue-Hui,Guo, Hai-Ming,Niu, Hong-Ying
p. 8575 - 8579
(2021/11/13)

An efficient and simple strategy toward the synthesis of highly functionalized compounds
The expedient syntheses of small libraries of ((β-ethoxycarbonyl, -cyano and -acetyl)propyloxy) methylphosphonate scaffolds bearing olefin, sulfanyl, or amine functions are described. All these new derivatives are readily produced from easily available starting reagents (aldehydes, electron-poor olefins, and dialkylphosphites) following a three steps reaction sequence of condensations, SN2′-type reaction and a conjugated thia- or aza-Michael 1,4-addition with aromatic and aliphatic thiol or amine nucleophiles.
Jmai, Momtez,Efrit, Mohamed Lotfi,Dubreuil, Didier,Blot, Virginie,Lebreton, Jacques,M'rabet, Hédi
p. 978 - 995
(2021/08/06)

Photoredox-Coupled F-Nucleophilic Addition: Allylation of gem-Difluoroalkenes
A novel strategy for the expedient construction of CF3-embeded tertiary/quarternary carbon centers was developed by taking advantage of photoredox catalysis. Thanks to a key step of single-electron oxidation, electron-rich gem-difluoroalkenes, which otherwise are essentially reluctant towards F-nucleoplilic addition, now readily participate in this fluoroallylation reaction. Furthermore, this strategy provides an elegant example for the generation, as well as functionalization, of α-CF3-substituted benzylic radical intermediates using cheap and readily available starting materials.
Liu, Haidong,Ge, Liang,Wang, Ding-Xing,Chen, Nan,Feng, Chao
p. 3918 - 3922
(2019/02/19)

Zinc-Mediated Double Addition on Functionalized Nitriles
Allylzinc reagents were used to access highly functionalized tertiary carbinamine derivatives in high yields from cyanoesters and cyanocarbonates. While the monoaddition of organometallics on nitriles is generally observed, in this work the nucleophilic a
Caillé, Julien,Pantin, Mathilde,Boeda, Fabien,Pearson-Long, Morwenna S.M.,Bertus, Philippe
p. 1329 - 1341
(2019/03/08)

Photoredox-Catalyzed Cyclopropanation of 1,1-Disubstituted Alkenes via Radical-Polar Crossover Process
The photoredox-neutral catalyzed cyclopropanation of 1,1-disubstituted alkenes via radical addition-anionic cyclization cascade has been successfully developed. Another new protocol based on photocatalytic allylation and cyclopropanation cascade was also described between allylic halide and halomethyl radical. In addition to the successful use of bis-catecholato silicates as the alkyl radical precursors, the acyl and alkyl radicals derived from 1,4-dihydropyridines were also engaged in this radical-polar crossover process. The competing experiments displayed that the 3-exo-tet mode of cyclization preferred over 4-exo and 5-exo cyclization modes, allowing for the selective 3-exo-tet cyclization. The superior nucleofuge character of bromide over chloride and tosylate has been demonstrated in the reaction of bromomethyl radical with homoallylic (pseudo)halides. This new protocol is characterized by its redox-neutral process, broad substrate scope, mild conditions, and good functional-group compatibility. (Figure presented.).
Luo, Wenping,Yang, Yi,Fang, Yewen,Zhang, Xinxin,Jin, Xiaoping,Zhao, Guicai,Zhang, Li,Li, Yan,Zhou, Wanli,Xia, Tingting,Chen, Bin
p. 4215 - 4221
(2019/08/16)

Intermolecular Aminoallylation of Alkenes Using Allyl-Oxyphthalimide Derivatives: A Case Study in Radical Polarity Effects
A case study on the polarity effects of radical mediated intermolecular alkene aminoallylation is presented herein. This radical group transfer method pairs vinyl ethers with electronically deficient allyl-oxyphthalimide derivatives to give difunctionalized products while illustrating the guiding effects of polarity on this radical reactivity.
Lardy, Samuel W.,Schmidt, Valerie A.
p. 6796 - 6799
(2019/11/03)

Catalytic Cleavage of C(sp2)-C(sp2) Bonds with Rh-Carbynoids
We report a catalytic strategy that generates rhodium-carbynoids by selective diazo activation of designed carbyne sources. We found that rhodium-carbynoid species provoke C(sp2)-C(sp2) bond scission in alkenes by inserting a monovalent carbon unit between both sp2-hybridized carbons. This skeletal remodeling process accesses synthetically useful allyl cation intermediates that conduct to valuable allylic building blocks upon nucleophile attack. Our results rely on the formation of cyclopropyl-I(III) intermediates able to undergo electrocyclic ring-opening, following the Woodward-Hoffmann-DePuy rules.
Wang, Zhaofeng,Jiang, Liyin,Sarró, Pau,Suero, Marcos G.
supporting information
p. 15509 - 15514
(2019/10/11)

Metal-Free C(sp3)-H Allylation via Aryl Carboxyl Radicals Enabled by Donor-Acceptor Complex
The first aryl carboxyl radical generation by the donor-acceptor complex with N-acyloxyphthalimides and Hantzsch esters is reported. Regio- and chemoselective C(sp3)-H bond allylation is enabled by aryl carboxyl radicals with visible light irradiation under mild and metal-free conditions.
Li, Yang,Zhang, Jing,Li, Defang,Chen, Yiyun
p. 3296 - 3299
(2018/06/11)

N-Arylamines Coupled with Aldehydes, Ketones, and Imines by Means of Photocatalytic Proton-Coupled Electron Transfer
A photoredox-catalyzed umpolung strategy for coupling reactions between aldehydes, ketones, imines, and N-arylamines is reported. These reactions proceed by a Br?nsted acid-activated proton-coupled electron transfer pathway, and the protocol was used to synthesize a broad scope of 1,2-amino alcohols and vicinal diamines, both of which are common motifs in biologically active natural products, pharmaceutically active molecules, and ligands.
Xia, Qing,Tian, Hao,Dong, Jianyang,Qu, Yi,Li, Lili,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
p. 9269 - 9273
(2018/06/04)

NEW PROCESSES AND INTERMEDIATES USEFUL IN SYNTHESIS OF NEP INHIBITORS
The invention relates to a novel process, novel process steps and novel intermediates useful in the synthesis of pharmaceutically active compounds, in particular neutral endopeptidase (NEP) inhibitors such as sacubitril, and prodrugs thereof.
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(2017/04/11)

Donor–Acceptor Complex Enables Alkoxyl Radical Generation for Metal-Free C(sp3)–C(sp3) Cleavage and Allylation/Alkenylation
The alkoxyl radical is an essential and prevalent reactive intermediate for chemical and biological studies. Here we report the first donor–acceptor complex-enabled alkoxyl radical generation under metal-free reaction conditions induced by visible light. Hantzsch ester forms the key donor–acceptor complex with N-alkoxyl derivatives, which is elucidated by a series of spectrometry and mechanistic experiments. Selective C(sp3)-C(sp3) bond cleavage and allylation/alkenylation is demonstrated for the first time using this photocatalyst-free approach with linear primary, secondary, and tertiary alkoxyl radicals.
Zhang, Jing,Li, Yang,Xu, Ruoyu,Chen, Yiyun
p. 12619 - 12623
(2017/09/11)

Catalytic Asymmetric Synthesis of Quaternary Barbituric Acids
The catalytic asymmetric α-functionalization of prochiral barbituric acids, a subtype of pseudosymmetric 1,3-diamides, to yield the corresponding 5,5-disubstituted (quaternary) derivatives remains essentially unsolved. In this study 2-alkylthio-4,6-dioxopirimidines are designed as key 1,3-diamide surrogates that perform exceedingly in amine-squaramide catalyzed C-C bond forming reactions with vinyl ketones or Morita-Baylis-Hillmann-type allyl bromides as electrophiles. Mild acid hydrolysis of adducts affords barbituric acid derivatives with an in-ring quaternary carbon in unprecedented enantioselectivity, offering valuable materials for biological evaluations.
Del Pozo, Sandra,Vera, Silvia,Oiarbide, Mikel,Palomo, Claudio
p. 15308 - 15311
(2017/11/06)

Palladium-Catalyzed Direct Intramolecular C-N Bond Formation: Access to Multisubstituted Dihydropyrroles
A palladium-catalyzed intramolecular amination of alkenes with retention of olefin functionalization was achieved under mild reaction conditions. In the presence of palladium catalyst, the tosyl-protected amine can directly couple with a double bond to provide versatile dihydropyrrole derivatives in moderate to excellent yields.
Jiang, Bing,Meng, Fei-Fan,Liang, Qiu-Ju,Xu, Yun-He,Loh, Teck-Peng
p. 914 - 917
(2017/02/26)

Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions
Pd-catalyzed intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by reduction of C(sp3)-Pd intermediate using diboron–water as a hydride source afforded enantioenriched 3,3-disubstituted oxindoles in high yields and enantioselectivities. When heavy water was used as a deuterium donor in combination with bis(catecholato)diboron (Cat2B2), deuterium was incorporated into the products with high synthetic efficiency. The ligand determined both the enantioselectivity of the reaction and the reaction pathways, thereby affording either hydroarylation (reductive Heck) or carboborylation products.
Kong, Wangqing,Wang, Qian,Zhu, Jieping
supporting information
p. 3987 - 3991
(2017/03/27)

Dental composition
An aqueous dental glass ionomer composition comprising (a) a reactive particulate glass, (b) a linear or branched polymer comprising acidic groups, which is reactive with the particulate glass in a cement reaction, whereby the linear or branched polymer comprising acidic groups has a polymer backbone and optionally pendant groups, (c) optionally dispersed nanoparticles comprising grafted linear or branched polymer chains comprising acidic groups, and having a polymer backbone characterized in that a polymer backbone of the linear or branched polymer of component (b) and/or, if present, the grafted Sinear or branched polymer chains of component (c) are obtainable a process comprising (i) cyclopolymerizing or cyclocopolymerizing one or more compounds of the following formula (I).
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Page/Page column 23; 24

(2017/07/14)

Synthesis and biological evaluation of 2-alkoxycarbonylallyl esters as potential anticancer agents
The reaction of carboxylic acids with Baylis-Hillman reaction derived α-bromomethyl acrylic esters readily provide 2-(alkoxycarbonyl)allyl esters in good to excellent yields. These functionalized allyl esters have been evaluated for their cell proliferation inhibition properties against breast cancer (MDA-MB-231 and 4T1) and pancreatic cancer (MIAPaCa-2) cell lines to explore their potential as anticancer agents. Several of the synthesized derivatives exhibit good potency against all three cancer cell lines. Our structure activity relationship (SAR) studies on 2-carboxycarbonyl allyl esters indicate that substituted aromatic carboxylic acids provide enhanced activity compared to substituted aliphatic carboxylic acid analogs. Di- and tri-allyl esters derived from di-and tri-carboxylic acids exhibit higher inhibition of cell proliferation than mono esters. Further SAR studies indicate that the double bond in the 2-(alkoxycarbonyl)allyl ester is required for its activity, and there is no increase in activity with increased chain length of the alkoxy group. Two lead candidate compounds have been identified from the cell proliferation inhibition studies and their preliminary mechanism of action as DNA damaging agents has been evaluated using epifluorescence and western blot analysis. One of the lead compounds has been further evaluated for its systemic toxicity in healthy CD-1 mice followed by anticancer efficacy in a triple negative breast cancer MDA-MB-231 xenograft model in NOD-SCID mice. These two in vivo studies indicate that the lead compound is well tolerated in healthy CD-1 mice and exhibits good tumor growth inhibition compared to breast cancer drug doxorubicin.
Ronayne, Conor T.,Solano, Lucas N.,Nelson, Grady L.,Lueth, Erica A.,Hubbard, Skyler L.,Schumacher, Tanner J.,Gardner, Zachary S.,Jonnalagadda, Sravan K.,Gurrapu, Shirisha,Holy, Jon,Mereddy, Venkatram R.
p. 776 - 780
(2017/02/18)

Generation of Alkoxyl Radicals by Photoredox Catalysis Enables Selective C(sp3)-H Functionalization under Mild Reaction Conditions
Reported herein is the first visible-light-induced formation of alkoxyl radicals from N-alkoxyphthalimides, and the Hantzsch ester as the reductant is crucial for the reaction. The selective hydrogen atom abstraction by the alkoxyl radical enables C(sp3)-H allylation and alkenylation reactions under mild reaction conditions at room temperature. Broad substrate variations, including a structurally complexed steroid, undergo the C(sp3)-H functionalization reaction effectively with high regio- and chemoselectivity.
Zhang, Jing,Li, Yang,Zhang, Fuyuan,Hu, Chenchen,Chen, Yiyun
p. 1872 - 1875
(2016/02/03)

Effect of Lewis acids and low temperature initiators on the allyl transfer reaction involving phthalimido-N-oxyl radical
Previously, we reported allyl transfer reactions of allyl bromide and allyl phthalimido-N-oxyl substrates with hydrocarbons that result in CC bond formation. In both cases, efficient chain transfer processes along with high reaction yields were observed. Since PINO chemistry leads to an environmentally friendly method of hydrocarbon functionalization, additional studies were performed in order to improve the process. To expand the utility of this reaction, we carried out experiments to optimize reaction conditions and tested the effect of Lewis acids and low temperature initiators. Although allyl-PINO substrates reacted slightly slower than the bromides, the reactions were cleaner with little or no side products. The chain lengths for these reactions were compromised at lower temperatures, attributable to the high activation energy required for the hydrogen atom abstraction by PINO. The addition of a Lewis acid catalyst (AlCl3) improves the product yield and reaction rate, possibly due to the formation of a PINO/AlCl3 complex which lowers the activation energy for hydrogen abstraction step.
Patil, Shradha,Chen, Liang,Tanko, James M.
supporting information
p. 7029 - 7033
(2015/01/09)

C-H Bond Functionalization with the Formation of a C-C Bond: A Free Radical Condensation Reaction Based on the Phthalimido-N-oxyl Radical
The development of a new chemical process that effects the conversion RH + C=C-C-X → R-C-C=C + HX, in which X is the phthalimido-N-oxyl radical (PINO·), is reported. The reaction yields are high, mass balances are excellent, and C-H bond functionalization and C-C bond formation are achieved in a single transformation. The byproduct of the reaction, N-hydroxyphthalimide, precipitates from solution and can be easily removed by simple filtration (and recycled). The kinetic chain lengths are shorter and the reaction times are longer (relative to those of the analogous reactions of allyl bromides), most likely because PINO· is a less-reactive hydrogen-atom abstractor. There appears to be no significant difference in efficiency in the addition-elimination steps. Competition experiments reveal that Br· and PINO· are comparable in leaving group ability.
Patil, Shradha,Chen, Liang,Tanko, James M.
supporting information
p. 502 - 505
(2015/10/05)

Synthesis of enantiopure β2-homoalanine derivatives via rhodium catalyzed asymmetric hydrogenation
The stereoselective synthesis of chiral β2-homoalanine derivatives with 99% ee by the Rh-catalyzed enantioselective hydrogenation of prochiral 2-aminomethyl acrylates is described. The subsequent transformation to chiral 3-amino-2-methylpropanols is also demonstrated.
Luehr, Susan,Holz, Jens,Zayas, Odalys,Seidelmann, Oliver,Domke, Lutz,Boerner, Armin
p. 395 - 401
(2013/06/27)

Total synthesis and absolute configuration of curvularides A-E
The first total synthesis of curvularides A-E, isolated from a culture broth of the endophytic fungus Curvularia geniculata, is described. The divergent total synthesis reported herein confirmed the absolute configurations of curvularides A-E and supported that these natural products might be obtained from a common biosynthetic pathway. The key steps involved in the synthesis were the diastereoselective hydrogenation of exo-methylene-γ-butyrolactone to α-methyl-γ-butyrolactone, Sharpless kinetic resolution, Sharpless asymmetric epoxidations, and intramolecular and intermolecular epoxide openings.
Sudhakar, Gangarajula,Satish, Kovela,Raghavaiah, Jakka
p. 10010 - 10020
(2013/01/15)

Scale-up of a chemo-biocatalytic route to (2 R,4 R)- and (2 S,4 S)-monatin
Monatin, a natural sweetener, refers to a collection of four isomers of 2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentanedioic acid. A chemo-biocatalytic approach to kilogram quantities of enantiopure 2S,4S-monatin and 2R,4R-monatin from indole is described. Key steps in the process include a (2 + 3) cycloaddition reaction followed by nickel-catalysed reduction to construct the monatin backbone, and a highly selective enzyme resolution of the 2S,4S- and 2R,4R-monatin diastereomeric pair to afford each enantiomer in 99% ee.
Rousseau, Amanda L.,Buddoo, Subash R.,Gordon, Gregory E. R.,Beemadu, Sharon,Kupi, B. Godfrey,Lepuru, M. Jerry,Maumela, Munaka C.,Parsoo, Arvesh,Sibiya, Duncan M.,Brady, Dean
experimental part
p. 249 - 257
(2011/10/02)

Synthesis and herbicidal activity of diphenyl ether derivatives containing unsaturated carboxylates
A series of novel diphenyl ether derivatives containing unsaturated carboxylates were designed and synthesized. Their structures were identified by 1H nuclear magnetic resonance and elemental analyses. The bioassays indicated that the compounds 5b and 5c exhibited good herbicidal activities against velvetleaf at a concentration of 30-40 g/hm2. The relationship between structure and herbicidal activity was also discussed. Among unsaturated carboxylates group, butenoate is the most promising one. Amonst them, 4-ethoxy-4-oxobutenyl 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2- nitrobenzoate 5b was identified as the most promising candidate due to its high protoporphyrinogen IX oxidase inhibition effect (pI50 = 6.64) and good herbicidal activity against broadleaf weeds with selectivity to soybean and low toxicity to mammals.
Yu, Haibo,Yang, Huibin,Cui, Dongliang,Lv, Liang,Li, Bin
scheme or table
p. 11718 - 11726
(2012/04/04)

Dental composition
An aqueous dental glass ionomer composition comprising (a) a reactive particulate glass, (b) a linear or branched polymer comprising acidic groups, which is reactive with the particulate glass in a cement reaction, whereby the linear or branched polymer comprising acidic groups has a polymer backbone and optionally pendant groups, (c) optionally dispersed nanoparticles comprising grafted linear or branched polymer chains comprising acidic groups, and having a polymer backbone characterized in that a polymer backbone of the linear or branched polymer of component (b) and/or, if present, the grafted linear or branched polymer chains of component (c) are obtainable a process comprising (i) cyclopolymerizing or cyclocopolymerizing one or more compounds of the following formula (I):
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(2011/05/08)

Synthesis of AE and BE ming analogues of the alkaloid methyllycaconitine
The synthesis of AE and BE analogues of the alkaloid methyllycaconitine is reported. The analogues contain two key pharmacophores: a 2-(2-methylmaleimido) benzoate ester and a homocholine motif formed from a tertiary N-(3-phenylpropyl)amine incorporated i
Guthmann, Holger,Conole, Daniel,Wrlght, Emma,Koerber, Karsten,Barker, David,Brimble, Margaret A.
experimental part
p. 1944 - 1960
(2009/09/06)

PRODUCTION OF MONATIN ENANTIOMERS
Methods for the preparation of the high intensity sweetener, monatin, 3-(1-amino-1,3-dicarboxy-3-hydroxy-but-4-yl)indole, its salts and internal condensation products thereof, including methods applicable to the large-scale production of monatin are described.
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Page/Page column 7-8; sheet 1; 3

(2009/04/24)

Domino palladium-catalyzed heck-intermolecular direct arylation reactions
A domino palladium-catalyzed Heck-intermolecular direct arylation reaction has been developed, giving access to a variety of dihydrobenzofurans, indolines, and oxindoles. A variety of sulfur-containing heterocycles such as thiazoles, thiophenes, and benzo
Rene, Olivier,Lapointe, David,Fagnou, Keith
supporting information; experimental part
p. 4560 - 4563
(2009/12/05)

Practical preparation of 2-halomethyl-allyl carboxylates
An improved, efficient preparation of 2-(halomethyl)allyl carboxylates starting from diethyl bis(hydroxymethyl) malonate and hydrobromic acid is reported. The allylic halogen of 2-(chloromethyl)acrylate and 2-(bromomethyl)acrylate are readily exchanged during esterification.
Sun, Chong-Si,Cheng, Hsiu-Yi,Lin, Yu-Shiang,Hou, Duen-Ren
p. 435 - 438
(2008/12/22)

Stereocontrolled synthesis and alkylation of cyclic β-amino esters: Asymmetric synthesis of a (-)-sparteine surrogate
A convenient method for the stereoselective synthesis of cyclic β-amino esters from an iodo αβ-unsaturated ester and α-methylbenzylamine is described. Subsequent enolate generation and alkylation proceeds with complete stereocontrol, with the two stereogenic centres working together. In this way, a functionalised piperidine suitable for alkaloid natural product synthesis was prepared. The usefulness of the methodology is exemplified with the concise synthesis of a (-)-sparteine surrogate. The Royal Society of Chemistry.
Hermet, Jean-Paul R.,Viterisi, Aurelien,Wright, Jonathan M.,McGrath, Matthew J.,O'Brien, Peter,Whitwood, Adrian C.,Gilday, John
p. 3614 - 3622
(2008/09/21)

Acid groups containing hydrolytically stable monomers
Monomer compound (I) is new. Monomer compound (I) of formula (R 1>-O-CO-C(=CHR)-Y 1>-O-Q(AH) n) is new. Either A : -CO 2->or SO 3->; or A+H +>AH; Q : 1-12C alkylene, 4-12C alkylene (interrupted by -O-,=N- or -S) or 6-15C arylene (optionally substituted by 1-4C alkyl, 1-4C alkoxy or halo), where arylene and aryl groups further carries acid groups A; Y 1>1-12C alkylene or 4-12C alkylene (interrupted by -O-, =N- or -S); R : CH 3or H; R 1>1-6C alkylene; and n : 1-3. Independent claims are also included for: (1) preparation of (I); (2) a composition comprising (I), a polymerizable monomer, optionally one/more initiator, and a filler, pigment and/or stabilizer; and (3) a dental material (II) comprising (I).
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Page/Page column 5

(2008/06/13)

Design, synthesis, and evaluation of aza inhibitors of chorismate mutase
The detailed information pertaining to this panel of aza inhibitors is presented. A series of aza inhibitors (4-9) of chorismate mutase (E.C. 5.4.99.5) was designed, prepared, and evaluated against the enzyme by monitoring the direct inhibition of the chorismate, 1, to prephenate, 2, conversion. None of these aza inhibitors displayed tighter binding to the enzyme than the native substrate chorismate or greater inhibitory action than the previously reported ether analogue, 3. Furthermore, no time-dependent loss of enzyme activity was observed in the presence of the two potentially reactive aza inhibitors (7 and 9). These results in conjunction with inhibition data from a broader series of chorismate mutase inhibitors allowed a novel proposal for the mechanistic role of chorismate mutase to be developed. This proposed mechanism was computationally verified and correlated with crystallographic studies of various chorismate mutases.
Hediger, Mark E.
p. 4995 - 5010
(2007/10/03)

DERIVATIVES OF SUCCINIC AND GLUTARIC ACIDS AND ANALOGS THEREOF USEFUL AS INHIBITORS OF PHEX
The present invention relates to derivatives of succinic and glutaric acids and analogues thereof, having the following general formula (I), useful as inhibitors of PHEX. These derivatives are useful for promoting generation of bone mass and treating or preventing diseases or conditions associated with a phosphate metabolism defect. Methods for preparation and intermediates are also disclosed.
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Page 47-48

(2010/02/07)

ALLYLIC CHAIN TRANSFER AGENTS
PCT No. PCT/AU94/00672 Sec. 371 Date Aug. 1, 1996 Sec. 102(e) Date Aug. 1, 1996 PCT Filed Nov. 2, 1994 PCT Pub. No. WO95/12568 PCT Pub. Date May 11, 1995A process for the free radical initiated polymerization of unsaturated species characterized by the us
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(2008/06/13)

Synthesis and dental aspects of acrylic phosphoric and phosphonic acids
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Zeuner,Moszner,Voelkel,Vogel,Rheinberger
p. 133 - 136
(2007/10/03)

Use of allylic trifiones for allylation of C-H bonds
Allylic trifiones react with THF and cyclohexane and related molecules to undergo a trifluoromethyl radical mediated C-H functionalization reaction. Due to polar effects, the reactions benefit from the presence of electron- withdrawing group at the 2-position of the allylic trifiones.
Xiang, Jason,Evarts, Jerry,Rivkin, Alexey,Curran, Dennis P.,Fuchs
p. 4163 - 4166
(2007/10/03)

Improved syntheses of ethyl α-(bromomethyl)acrylate and 2-methylene-1,3- propanediol via ethyl α-(hydroxymethyl)acrylate
Ethyl α-(bromomethyl)acrylate (1) and 2-methylene-1,3-propanediol (2) have been prepared via formalhedyde addition to ethyl acrylate in the presence of DABCO, giving α, β-unsaturated ester 3. Reduction of hydroxy ester 3 with one equivalent of alane, then borohydride reduction of the resulting aldehyde 4 gives 2.
Byun,Reddy,Bittman
p. 1371 - 1374
(2007/10/02)

ANTITUMOR ETHER LIPIDS: AN IMPROVED SYNTHESIS OF ILMOFOSINE AND AN ENANTIOSELECTIVE SYNTHESIS OF AN ILMOFOSINE ANALOG
Efficient routes to racemic Ilmofosine (1) and to the enantimers of its oxygen analog, 2'-(trimethylammonio)ehtyl 3-hexadecyloxy-2-methoxymethylpropanephospahte (2), are described starting from ehtyl α-(hydroxymethyl)acrylate (3) or 2-methylene-1,3-propanediol (6).
Reddy, Kasireddy Chandraprakash,Byun, Hoe-Sup,Bittman, Robert
p. 2679 - 2682
(2007/10/02)

Ethyl α-(hydroxymethyl)acrylate
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Villieras,Rambaud
p. 220 - 220
(2017/05/18)

Double-Headed Haptens with Pyrocatechol (Poison Ivy like) and Methylene Lactone Functional Groups: A Search for Skin-Tolerance Inducers
In order to develop new theories for desensitization, a potential skin sensitizer, 1, with two different haptenic ends, (a) a pyrocatechol group and (b) an α-methylene-γ-butyrolactone moiety, separated by a straight nine-carbon-atom chain has been prepare
Mattes, Henri,Benezra, Claude
p. 165 - 168
(2007/10/02)

Syntheses in the isocamphane series, XXI: The synthesis of isocamphaneanalogous drugs
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Buchbauer,Steigenberger,Bauer,Morbitzer
p. 176 - 183
(2007/10/02)

Methyl α-(bromomethyl)acrylate
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Cassady, John M.,Howie, Gary A.,Robinson, J. Michael,Stamos, Ioannis K.
p. 77 - 77
(2017/05/20)

Ethyl α-(bromomethyl)acrylate
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Ramarajan,Ramalingam,O'Donnell,Berlin
p. 56 - 56
(2017/05/16)

Wittig-Horner Reaction in Heterogeneous Media; 1. An Easy Synthesis of Ethyl α-Hydroxymethylacrylate and Ethyl α-Halomethylacrylates using Formaldehyde in Water
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Villieras, Jean,Rambaud, Monique
p. 924 - 926
(2007/10/02)