- Structure-activity relationship observations for the bagworm moth pheromone
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Structure-activity relationship (SAR) observations were made for the bagworm moth pheromone. (R)-2-pentyl decanoate, and a series of analogs with modifications in the alcohol portion of the molecule. Observed attractiveness of these analogs was related to molecular structure and their physical attributes using computational chemistry. Electrostatic potential and Van der Waals (VdW) electrostatic coded surface three-dimensional (3D) maps of the molecular mechanics (MM) minimized lowest energy conformation of the pheromone show that size, shape, charge distribution, and chirality of the molecule are related to attractiveness.
- Warthen,Klun,DeVilbiss
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Read Online
- Functionalization of α-C(sp3)?H Bonds in Amides Using Radical Translocating Arylating Groups
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α-C?H arylation of N-alkylamides using 2-iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α-quaternary carbon centers in amides. Various mono- and disubstituted RTA-groups are applied to the arylation of primary, secondary, and tertiary α-C(sp3)?H-bonds. These radical transformations proceed in good to excellent yields and the cascades comprise a 1,6-hydrogen atom transfer, followed by a 1,4-aryl migration with subsequent SO2 extrusion.
- Radhoff, Niklas,Studer, Armido
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supporting information
p. 3561 - 3565
(2021/01/04)
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- Rational Design of Thermodynamic and Kinetic Binding Profiles by Optimizing Surface Water Networks Coating Protein-Bound Ligands
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A previously studied congeneric series of thermolysin inhibitors addressing the solvent-accessible S2′ pocket with different hydrophobic substituents showed modulations of the surface water layers coating the protein-bound inhibitors. Increasing stabilization of water molecules resulted in an enthalpically more favorable binding signature, overall enhancing affinity. Based on this observation, we optimized the series by designing tailored P2′ substituents to improve and further stabilize the surface water network. MD simulations were applied to predict the putative water pattern around the bound ligands. Subsequently, the inhibitors were synthesized and characterized by high-resolution crystallography, microcalorimetry, and surface plasmon resonance. One of the designed inhibitors established the most pronounced water network of all inhibitors tested so far, composed of several fused water polygons, and showed 50-fold affinity enhancement with respect to the original methylated parent ligand. Notably, the inhibitor forming the most perfect water network also showed significantly prolonged residence time compared to the other tested inhibitors.
- Krimmer, Stefan G.,Cramer, Jonathan,Betz, Michael,Fridh, Veronica,Karlsson, Robert,Heine, Andreas,Klebe, Gerhard
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p. 10530 - 10548
(2016/12/16)
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- Unactivated C(sp3)-H hydroxylation through palladium catalysis with H2O as the oxygen source
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A novel palladium catalyzed hydroxylation of unactivated aliphatic C(sp3)-H bonds was successfully developed. Different from conventional methods, water serves as the hydroxyl group source in the reaction. This new reaction demonstrates good reactivity and broad functional group tolerance. The C-H hydroxylated products can be readily transformed into various highly valuable chemicals via known transformations. Based on experimental and theoretical studies, a mechanism involving the Pd(ii)/(iv) pathway is proposed for this hydroxylation reaction.
- Hu, Jiantao,Lan, Tianlong,Sun, Yihua,Chen, Hui,Yao, Jiannian,Rao, Yu
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supporting information
p. 14929 - 14932
(2015/10/06)
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- Use of ethyl (benzothiazol-2-ylsulfonyl)acetate for malonic ester-type syntheses of carboxylic acids and esters
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A new methodology for the synthesis of substituted carboxylic acids is described. Alkylation of either ethyl (benzothiazol-2-ylsulfonyl)acetate or ethyl 2-(benzothiazol-2-ylsulfonyl)propionate was achieved with alkyl halides and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane solution. These products were then desulfinated and hydrolysed in one-pot under mild conditions to give substituted acetic acids in good-to-excellent yields.
- Hussein, Waleed M.,McGeary, Ross P.
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p. 1222 - 1227
(2014/10/16)
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- Developing Pd(II) catalyzed double sp3 C-H alkoxylation for synthesis of symmetric and unsymmetric acetals
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An effective Pd(II) catalyzed double unactivated C(sp3)-H alkoxylation has been developed to prepare both symmetric and unsymmetric acetals. This new reaction demonstrates good functional group tolerance, excellent reactivity, and high yields. A variety of novel acetals can be readily accessed via this new method. (Chemical Equation Presented).
- Zong, Yu,Rao, Yu
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supporting information
p. 5278 - 5281
(2015/01/09)
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- SPIROBENZYLAMINE-PHOSPHINE, PREPARATION METHOD THEREFOR AND USE THEREOF
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The present invention relates to a spirobenzylamine-phosphine, preparation method therefor and use thereof. The compound has a structure represented by formula (I), wherein n=0 to 3; R1, R2, R3, R4, R5, R6, R7, R8 and R9 having a value as defined in claim 1. Starting from the substituted 7-trifluoromesyloxy-7'-diarylphosphino-1, 1'-spiro-dihydroindene, the compound is synthesized in a two-step or three-step reactions. The new spirobenzylamine-phosphine is complexed with an iridium precursor and is subjected to ion exchange, to give an Iridium/spirobenzylamine-phosphine complex comprising various anions. The spiro benzyl amine-phosphine/Iridium complex according to the present invention may be used for catalyzing asymmetry hydrogenation of a variety of alpha-substituted acrylic acids, has high activity and enantio-selectivity, and has a good prospect of industrialization.
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Paragraph 0067
(2014/07/22)
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- Spirobenzylamine-Phosphine, Preparation Method Therefor And Use Thereof
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The present invention relates to a spirobenzylamine-phosphine, preparation method therefor and use thereof. The compound has a structure represented by formula (I), wherein n=0 to 3; R1, R2, R3, R4, R5, R6, R7, R8 and R9 having a value as defined in claim 1. Starting from the substituted 7-trifluoromesyloxy-7′-diarylphosphino-1,1′-spiro-dihydroindene, the compound is synthesized in a two-step or three-step reactions. The new spirobenzylamine-phosphine is complexed with an iridium precursor and is subjected to ion exchange, to give an Iridium/spirobenzylamine-phosphine complex comprising various anions. The spiro benzyl amine-phosphine/Iridium complex according to the present invention may be used for catalyzing asymmetry hydrogenation of a variety of alpha-substituted acrylic acids, has high activity and enantio-selectivity, and has a good prospect of industrialization.
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Paragraph 0078; 0079
(2014/07/22)
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- Efficient diastereoselective synthesis of (2R,3R,4R)-2-amino-3-hydroxy-4,5- dimethylhexanoic acid, the lactone linkage unit of homophymine A
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For the total synthesis of novel cyclodepsipeptide homophymine A, (2R,3R,4R)-2-amino-3-hydroxy-4,5- dimethylhexanoic acid was successfully synthesized by Evans' asymmetric alkylation and the anti-selective asymmetric hydrogenation of a chiral α-amino-β-keto ester as the key steps.
- Ohtaka, Junpei,Hamajima, Akinari,Nemoto, Tetsuhiro,Hamada, Yasumasa
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p. 245 - 250
(2013/03/28)
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- Syntheses and evaluation of anticonvulsant activity of novel branched alkyl carbamates
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A novel class of 19 carbamates was synthesized, and their anticonvulsant activity was comparatively evaluated in the rat maximal electroshock (MES) and subcutaneous metrazol (scMet) seizure tests and pilocarpine-induced status epilepticus (SE) model. In spite of the alkyl-carbamates' close structural features, only compounds 34, 38, and 40 were active at the MES test. The analogues 2-ethyl-3-methyl-butyl-carbamate (34) and 2-ethyl-3-methyl-pentyl- carbamate (38) also exhibited potent activity in the pilocarpine-SE model 30 min postseizure onset. Extending the aliphatic side chains of homologous carbamates from 7 to 8 (34 to 35) and from 8 to 9 carbons in the homologues 38 and 43 decreased the activity in the pilocarpine-SE model from ED50 = 81 mg/kg (34) to 94 mg/kg (35) and from 96 mg/kg (38) to 114 mg/kg (43), respectively. The most potent carbamate, phenyl-ethyl-carbamate (47) (MES ED50 = 16 mg/kg) contains an aromatic moiety in its structure. Compounds 34, 38, 40, and 47 offer the optimal efficacy-safety profile and, consequently, are promising candidates for development as new antiepileptics.
- Hen, Naama,Bialer, Meir,Yagen, Boris
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experimental part
p. 2835 - 2845
(2012/06/15)
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- Enantioselective hydrogenation of α-substituted acrylic acids catalyzed by iridium complexes with chiral spiro aminophosphine ligands
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Highly active: Iridium complexes with chiral spiro aminophosphine ligands were synthesized and applied as catalysts for the asymmetric hydrogenation of α-substituted acrylic acids (see scheme). The complexes were highly active catalysts, showing turnover frequencies of up to 6000 h-1, and catalyst loadings could be reduced to 0.01 mol %. Copyright
- Zhu, Shou-Fei,Yu, Yan-Bo,Li, Shen,Wang, Li-Xin,Zhou, Qi-Lin
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supporting information; experimental part
p. 8872 - 8875
(2012/10/08)
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- Cu(I)-catalyzed, α-selective, allylic alkylation reactions between phosphorothioate esters and organomagnesium reagents
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Regiocontrol of allylic alkylation reactions involving hard nucleophiles remains a significant challenge and continues to be an active area of research. The lack of general methods in which α-alkylation is favored underscores the need for the development of new processes for achieving this type of selectivity. We report that Cu(I) catalyzes the allylic substitution of phosphorothioate esters with excellent α-regioselectivity, regardless of the nature of the Grignard reagent that is used. To the best of our knowledge, the Cu-catalyzed allylic alkylation of phosphorothioate esters has never been described. We have also developed a simple protocol for inducing high α selectivity starting from secondary allylic halides. This is accomplished by using sodium phosphorothioates as an additive.
- Lauer, Andrew M.,Mahmud, Farzeen,Wu, Jimmy
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experimental part
p. 9119 - 9123
(2011/08/04)
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- Synthesis and evaluation of antiallodynic and anticonvulsant activity of novel amide and urea derivatives of valproic acid analogues
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Valproic acid (VPA, 1) is a major broad spectrum antiepileptic and central nervous system drug widely used to treat epilepsy, bipolar disorder, and migraine. VPA's clinical use is limited by two severe and lifethreatening side effects, teratogenicity and hepatotoxicity. A number of VPA analogues and their amide, N-methylamide and urea derivatives, were synthesized and evaluated in animal models of neuropathic pain and epilepsy. Among these, two amide and two urea derivatives of 1 showed the highest potency as antineuropathic pain compounds, with ED50 values of 49 and 51 mg/kg for the amides (19 and 20) and 49 and 74 mg/kg for the urea derivatives (29 and 33), respectively. 19, 20, and 29 were equipotent to gabapentin, a leading drug for the treatment of neuropathic pain. These data indicate strong potential for the above-mentioned novel compounds as candidates for future drug development for the treatment of neuropathic pain. 2009 American Chemical Society.
- Kaufmann, Dan,Bialer, Meir,Shimshoni, Jakob Avi,Devor, Marshall,Yagen, Boris
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experimental part
p. 7236 - 7248
(2010/07/04)
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- Enantioselective Friedel-Crafts reactions of ethenetricarboxylates and substituted pyrroles and furans and intramolecular reaction of benzene derivatives
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Compared to enantioselective Friedel-Crafts reactions of indoles, reactions of alkylidene malonates with monocyclic aromatic compounds generally proceed with low enantioselectivity. The Friedel-Crafts reactions of ethenetricarboxylates 1 and monocyclic heteroaromatic compounds, such as substituted pyrroles and furans were investigated. The reaction of 1 with 2,4-dimethylpyrrole in the presence of a chiral bisoxazoline-copper(II) complex (10 mol %) in tetrahydrofuran at room temperature gave alkylated products in up to 72% ee. The reaction of 1 with 2-substituted furans gave alkylated products in 46-62% ee. The absolute stereochemistry of the furan Friedel-Crafts product 7e was determined by transformation to the known 2,3-dimethylbutyric acid. The intramolecular reaction of benzene derivatives gave cyclized products up to 56% ee.
- Yamazaki, Shoko,Kashima, Shinichi,Kuriyama, Taiki,Iwata, Yuko,Morimoto, Tsumoru,Kakiuchi, Kiyomi
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experimental part
p. 1224 - 1234
(2009/10/24)
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- Structure and reactivity in the hydrolyses of aliphatic carboxylic acid esters and chlorides
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For hexanoic acid and its seven isomers, relative rates have been determined for acid catalysed esterification with methanol, and compared with those for saponification of the methyl esters. A good correlation between logarithms of relative rates for the two reactions is obtained, and it is suggested that the eight isomers provide a test set of compounds in which steric effects alone act on reactivity at the acyl carbon. A full set of steric parameters (Es′ values) are presented. Rates of solvolyses of the acid chlorides- of the isomers have been determined conductometrically in 3:1 wt:wt acetonitrile water. Logarithms of relative rates show a poor correlation with Es′, and, taking into account the solvent dependence of the rates, the pattern excludes both rate-limiting formation of a tetrahedral intermediate and rate-limiting dissociation of chloride to form acylium ions. The remaining possibilities, a concerted process (ANDN?) and rapid reversible formation of a hydrate followed by rate-limiting dissociation of chloride (AN + DN?,) are considered. Copyright
- Regan, Andrew C.,Watt, C. Ian F.
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p. 180 - 189
(2008/02/06)
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- Highly diastereoselective preparation of (E)-alkenylsilanes bearing an α-chiral center
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(Chemical Equation Presented) The copper(I)-mediated anti-S N2′ allylic substitution allows a highly stereoselective preparation of alkenylsilanes bearing a chiral center in the α-position with high transfer of chirality. These alkenylsilanes were converted into α,β-unsaturated ketones or into the corresponding boronic esters without loss of the chiral information.
- Perrone, Sylvie,Knochel, Paul
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p. 1041 - 1044
(2008/02/01)
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- Stereoselective addition of organometallic reagents to N-(tosyl)vinylsulfoximines
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Treatment of N-(toluene-p-sulfonyl)vinylsulfoximines 3 with methyllithium at -78°C, followed by addition of chlorotrimethylsilane, results in the efficient formation of α-silyl vinylsulfoximines 6 in good to excellent yield. Nucleophilic addition of a range of simple alkyl and aryl organometallics (lithium, copper-lithium and Grignard reagents) occurs in variable yield to give the Michael adducts 8 with organolithium reagents most effective. The degree of stereoselectivity of each of the addition reactions was determined by 1H NMR of the desilylated products 9, and proved to be synthetically useful for compounds in which the starting α-silylvinylsulfoximines were branched at the γ-position, and also when phenylhthium was used as the nucleophile. The sense of stereoselectivity was determined in two cases by X-ray crystal structure analyses (of 9e and 9i). A one-pot process for the conversion of α-silylvinylsulfoximines 6 to α-substituted carboxylic acids 11 was developed, using an in situ phenylselenation-oxidation process following the initial conjugate addition. Use of enantiomerically pure starting materials allowed the assignment of configuration of two carboxylic acids (13e and 13h) by comparison with literature data, and hence indirectly of the relative stereochemistry of the initial Michael adducts 9e and 9h.
- Jackson, Richard F. W.,Briggs, Andrew D.,Brown, Paul A.,Clegg, William,Elsegood, Mark R. J.,Frampton, Christopher
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p. 1673 - 1682
(2007/10/03)
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- Highly efficient enantioselective synthesis of optically active carboxylic acids by Ru(OCOCH3)2[(S)-H8-BINAP]
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In the presence of a catalytic amount of Ru(OCOCH3)2[(S)-H8-BINAP] [H8-BINAP = 2,2′-bis-(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′- octahydro-1,1′-binaphthyl], the asymmetric hydrogenation of α,β- and β,γ-unsaturated carboxylic acids afforded the corresponding saturated carboxylic acids in higher enantiomeric excesses and at faster reaction rates than those using the Ru(OCOCH3)2[(R)-BINAP] catalyst [BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]. The hydrogenation of (E)-2-alkyl-2-alkenoic acids by the H8-BINAP catalyst system produced saturated acids in 95-97% ee. 2-Methylcinnamic acid was treated with H8-BINAP-Ru(II) complex as a catalyst to yield a hydrogenated product in much higher ee than that produced by BINAP-Ru(II) (89 and 30% ee, respectively). This homogeneous catalysis using H8-BINAP-Ru(II) established a promising synthetic route to (S)-ibuprofen in up to 97% ee. Asymmetric hydrogenation of β-disubstituted acrylic acids also proceeded smoothly with good enantioselectivities (70-93% ee). In addition, the hydrogenation of trisubstituted acrylic acids (up to 88% ee) was investigated. Hydrogen pressure effect on the sense and level of enantioselection was shown to be substrate dependent. The difference between the H8-BINAP- and BINAP-Ru(II) complexes was also discussed.
- Uemura, Toshitsugi,Zhang, Xiaoyoung,Matsumura, Kazuhiko,Sayo, Noboru,Kumobayashi, Hidenori,Ohta, Tetsuo,Nozaki, Kyoko,Takaya, Hidemasa
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p. 5510 - 5516
(2007/10/03)
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- Antiparasitic agents
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The invention provides novel compounds having the formula: STR1 wherein R when taken individually is H; R1 when taken individually is H or OH; R and R1 when taken together represent a double bond; R2 is an alpha-branched C3 -C8 alkyl, alkenyl, alkynyl, alkoxyalkyl or alkylthioalkyl group; a C3 -C8 cycloalkyl, C5 -C8 cycloalkenyl or C5 -C8 cycloalkylalkyl group, any of which may be substituted by methylene or one or more C1 -C4 alkyl groups or halo atoms; or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may be substituted by one or more C1 -C4 alkyl groups or halo atoms; R3 is hydrogen or methyl; R4 is H or 4'-(alpha-L-oleandrosyl)-alpha-L-oleandrosyloxy with the proviso that when R2 is alkyl it is not isopropyl or sec-butyl; when R4 is H, each of R and R1 is H, and R2 is not methyl or ethyl; and when R4 is H, R is H, R1 is OH, and R2 is not 2-buten-2-yl, 2-penten-2-yl or 4-methyl-2-penten-2-yl. The compounds are broad spectrum antiparasitic agents having utility as anthelmintics, ectoparasiticides, insecticides and acaricides. The invention also provides a process for producing the novel avermectin and milbemycin derivatives by adding a carboxylic acid or derivative thereof to a fermentation of an avermectin or milbemycin producing organism.
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- SYNTHESIS OF BRASSINOLIDE AND ITS ANALOGS
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A new version of the synthesis of brassinosteroids of the 28C series is described.It is based on stigmasterol and uses the reaction of steroidal 22-aldehydes with aryl sulfones.
- Khripach, V. A.,Zhabinskii, V. N.,Ol'khovik, V. K.,Lakhvich, F. A.
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p. 1699 - 1706
(2007/10/02)
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- A Facile Method for Synthesis of Three Carbon-Homologated Carboxylic Acid by Regioselective Ring-opening of β-Propiolactones with Organocopper Reagents
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Organocopper reagents, such as diorganocuprates, organocopper-tributylphosphine, and Grignard reagents in the presence of a copper (I) salt, reacted with β-propiolactones by regioselective β-carbon-oxygen fission to give 3-substituted propionic acids.Among these three kinds of organocopper reagents, diorganocuprate, especially halomagnesium cuprate gave the highest yields of the acids, which was remarkably observed in the ring-opening of sterically hindered β-propiolactones such as β-methyl- and α,β-dimethyl-β-propiolactones and also in the reactions using the organocopper reagents with vinyl and allyl substituents.The ring-opening of β-propiolactone was confirmed to proceed by SN2 pathway with predominant inversion of configuration of the β-carbon by using the reaction of cis-α,β-dimethyl-β-propiolactone with di-tert-butylcuprate to afford syn-2,3,4,4-tetramethylpentanoic acid.
- Kawashima, Masatoshi,Sato, Toshio,Fujisawa, Tamotsu
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p. 403 - 412
(2007/10/02)
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- Reaction of Carbocations Derived from Alkanes with Carbon Monoxide in HF-SbF5 Superacid
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Alkanes readily react with CO and H2O in HF-SbF5 at 30 deg C under atmospheric pressure and give considerably different product distributions from those in the usual Koch-Haaf reaction.When using C5- or C6-alkanes with tertiary C-H bonds, a considerable amount of secondary carboxylic acids are produced by the reaction of CO with secondary alkyl cations.Such cations may appear as transient intermediates in the course of the carbon skeletal isomerization of initially formed tertiary cations.For the straightchain alkanes, the protonolysis at C-C bonds initiated the reaction to give fragment alkyl cations.This resulted in the formation of carboxylic acids with a lower number of carbon atoms than the starting alkanes.Intermolecular hydride shift between the fragment cations and the starting alkanes occured at the same time to form a large amount of carboxylic acids with the alkyl group of the same number of carbon atoms as the starting alkane.On the other hand, for alkanes with more than seven carbon atoms, β-scission occurs exclusively to produce C4-, C5-, and C6-carboxylic acids.
- Yoneda, Norihiko,Takahashi, Yukio,Fukuhara, Tsuyoshi,Suzuki, Akira
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p. 2819 - 2826
(2007/10/02)
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- Synthesis of 4,4-Disubstituted 1,3-Thiazol-5(4H)-thiones
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An easy synthesis for the 1,3-thiazol-5(4H)-thiones 5, a class of heterocycles which have hitherto only been available with difficulty, is described.Reaction of 3-amino-2H-azirines 25 with thiocarboxylic acids at 0 deg yields monothiodiamides of type 20 (Scheme 6) which, on treatment with Lawesson reagent at 100 deg, undergo thiation and cyclization to give 5 in good yield.
- Jenny, Christjohannes,Heimgartner, Heinz
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p. 374 - 388
(2007/10/02)
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- New Methods and Reagents in Organic Synthesis. 26. Reductive Desulfonylation of α-Sulfonylacetates
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α-Acyl-benzylsulfonyldiazomethanes (2a-d) have been converted to α-benzylsulfonyl-α-substituted-acetic acids (7a-d) by means of the Wolff rearrangement.Reductive removal of the benzylsulfonyl group of 7b-d can be achieved by the use of sodium-ethanol in tetrahydrofuran. α-Benzylsulfonyl-α-substituted-propionic acids (9a-d), prepared from benzyl α-benzylsulfonyl-α-substituted-acetates (3a-d), were also debenzylsulfonylated under similar reductive conditions.The overall process, in combination with the Arndt-Eistert synthesis of α-sulfonylacetates from acyl chlorides and benzylsulfonyldiazomethane (1), provides a new, safe method for the homologation of carboxylic acids.Keywords-reductive desulfonylation; Wolff rearrangement; sodium amalgam reduction; catalytic debenzylation; sodium-ethanol reduction; methylation; α-substituted propionic acid; α-sulfonylacetate
- Kuo, Ying-Che,Aoyama, Toyohiko,Shioiri, Takayuki
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p. 2787 - 2792
(2007/10/02)
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- Specificities of the α-Alkynone Cyclization
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Die Regio- und Stereospezifitaeten der α-Alkinon-Cyclisierung, einer thermischen Umwandlung von Alkinyl-alkyl-ketonen, welche in β'-Stellung mindestens ein H-Atom tragen, zu 2-Cyclopentenonen wurden untersucht.Cyclisierung zum hoeher substituierten C(β')-Atom ist dabei bevorzugt, vorausgesetzt, dass die zur Insertion zur Verfuegung stehende C(β'),H-Bindung zur Propioloylseitenkette eine moeglichst synplanare Anordnung einnehmen kann.In Cyclisierungen zu β'-Methylen-C-Atomen, welche diastereotope H-Atome tragen, wird daher eines der moeglichen epimeren Produkte bevorzugt oder ausschliesslich gebildet.Die mechanistischen Konsequenzen der gefundenen Specifitaeten werden diskutiert.
- Karpf, Martin,Huguet, Joan,Dreiding, Andre S.
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- A THREE CARBON HOMOLOGATION BY THE RING-OPENING OF β-PROPIOLACTONES WITH DIORGANOCUPRATES
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Various organocuprates react with β-propiolactones to give β-substituted propionic acids in high yields.
- Fujisawa, Tamotsu,Sato, Toshio,Kawara, Tatsuo,Kawashima, Masatoshi
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p. 2181 - 2184
(2007/10/02)
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