cas 21161-11-5, 2-NITRO-ISOPHTHALIC ACID | Articles data

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3,3′-Diiodobinaphthol and 3,3′-Diiodobiphenol Derivatives as Hypervalent Iodine Organocatalysts for the α-Oxytosylation of Ketones
New series of enantiopure 3,3′-diiodobinaphthol- and 3,3′-diiodobiphenol-based molecules have been synthesized and used as chiral hypervalent iodine oxidation organocatalysts in the α-oxytosylation of propiophenone. When we compared these new organocatalysts to our previous series of 3,3′-diiodo-1,1′-binaphthalene-2,2′-diol-fused maleimides, we have made two important observations: the maleimide moiety is the best moiety for obtaining moderate enantioselectivities, and the presence of an aliphatic substituent on the biaryl part of the catalyst enhances the enantioselectivity.
Brenet, Simon,Minozzi, Clémentine,Clarens, Bastien,Amiri, Lilia,Berthiol, Florian
p. 3859 - 3873
(2015)
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Photodegradable bridged silane and preparation method thereof
The invention relates to photodegradable bridged silane and a preparation method thereof. The photodegradable bridged silane has a structure as shown in a formula I which is described in the specification. The method comprises the following steps: taking 1, 3-dimethyl-2-nitrobenzene as a raw material, carrying out oxidation reaction to obtain 2-nitro 1, 3-phthalic acid, carrying out reduction reaction on a carboxylic acid group to obtain 2-nitro-1, 3-benzenedimethanol, carrying out acylation reaction on the 2-nitro-1, 3-benzenedimethanol and chloroacetyl chloride to obtain 2-nitro-1, 3-benzenedichloroacetate, and finally carrying out substitution reaction on the 2-nitro-1, 3-benzenedichloroacetate and amino-containing silane to obtain the photodegradable bridged silane containing 2-nitrobenzyl. The photodegradable bridged silane obtained in the invention has good photoresponse performance, can be used for designing and preparing photoresponsive functional materials, and has important application value. The synthesis process is simple, raw materials are easy to obtain, reaction conditions are mild, and operability is high.
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Paragraph 0065-0067; 0072-0076; 0080-0084; 0088-0092; 0096

(2020/12/29)

SELF-IMMOLATIVE SYSTEMS
The present invention is concerned with self-immolative recognition and/or responsive systems for electrophilic compounds, especially alkylating agents, which systems may comprise disclosure or detection of the alkylating agent. The present invention is especially concerned with non-protic triggered self-immolative systems, molecules, and methods, and in particular for detection of non- protic electrophilic agents, and especially alkylating agents, for example alkyl or benzylic halides, which may be found in pesticides or fumigants, or chemical warfare agents.
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Page/Page column 11; 26; 27

(2020/05/28)

DOX-UCNPs@mSiO2-TiO2 nanocomposites for near-infrared photocontrolled chemo/photodynamic therapy
Currently, incorporating multiple therapeutic functions into one nanostructure has attracted more and more attention for the development of efficient anticancer agents. In this study, a uniform core-shell UCNPs@mSiO2 nanocomposite was prepared as the carrier to develop the NIR light-controlled chemotherapy associated with photodynamic therapy (PDT). In view of the novel UV emission, the semiconductor photosensitizer TiO2 was exploited due to its high efficiency and chemical stability. The host modification method was used to integrate TiO2 doping and mesoporous structure, which can store anticancer drug molecules (doxorubicin, DOX). To improve the utilization of emission, a photolabile o-nitrobenzyl derivative was incorporated to form a sensitive linker (NB linker) as a "gate" to make sure the few leak. Upon NIR irradiation, the UV emission can not only excite TiO2 to produce reactive oxygen species (ROS), but also induce the breaking of NB linker as well as drug release. The NIR-triggered performances were further demonstrated by the cell experiment using HeLa cells as the model cancer cell. The synergistic effect of chemotherapy and PDT induces enhanced cytotoxicity, which is more powerful than their simple effects added together. Therefore, the novel NIR light-controlled double-therapeutic nanocomposite should be a potential candidate for anticancer agents.
Chen, Yuhua,Tong, Ruihan,An, Na,Lin, Huiming,Qu, Fengyu
supporting information
p. 7292 - 7301
(2017/08/02)

PROGRAMMED DEGRADATION OF POLYMERS DERIVED FROM BIOMASS
Novel photodegradable polymers derived from biomass are provided, together with methods of making and methods of using said polymers.
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(2016/05/10)

Multistimuli-responsive hydrogel particles prepared via the self-assembly of PEG-based hyperbranched polymers
Generally, it is very difficult to obtain multistimuli-responsive hydrogel particles. Here, we introduce a novel method for the preparation of multistimuli-responsive hydrogel particles by adding water into the poly(ethylene glycol) (PEG)-based hyperbranched polymers. The produced PEG-base polymers via reversible addition-fragmentation chain transfer (RAFT) polymerization become temperature-sensitive and less soluble when heated above the lower critical solution temperature (LCST) after directly adding water. Subsequently, the hydrogel particles can be formed via hyperbranch-hyperbranch coupling through disulfide exchange. The resulting hydrogel particles are temperature-, photo-, and redox-responsive.
Chen, Qian-Bao,You, Ye-Zi
supporting information
p. 677 - 679
(2015/05/27)

Programmed photodegradation of polymeric/oligomeric materials derived from renewable bioresources
Renewable polymeric materials derived from biomass with built-in phototriggers were synthesized and evaluated for degradation under irradiation of UV light. Complete decomposition of the polymeric materials was observed with recovery of the monomer that was used to resynthesize the polymers.
Rajendran, Saravanakumar,Raghunathan, Ramya,Hevus, Ivan,Krishnan, Retheesh,Ugrinov, Angel,Sibi, Mukund P.,Webster, Dean C.,Sivaguru, Jayaraman
supporting information
p. 1159 - 1163
(2015/01/30)

Hydrogen bonding behavior of amide-functionalized α-diimine palladium complexes
A class of (N,N′-diaryl-α-diimine)Pd complexes bearing amide substituents on the N-aryl rings is described. Hydrogen bonding interactions involving the amide groups influence the structures, isomer distributions, and ligand coordination behavior of these compounds. The amide-functionalized α-diimine ligands (2,6-iPr2-Ph)N=CMeCMe=N(2-C(=O)NMe2-6-iPr-Ph) (4a), (2,6-iPr2-Ph)N=CMeCMe=N(2,6-(C(=O)NMe2)2-Ph) (4b), and (2-C(=O)NMe2-6-iPr-Ph)N=CMeCMe=N(2-C(=O)NMe2-6-iPr-Ph) (4c) were prepared by condensation reactions of 2,3-butanedione and the appropriate anilines. The attempted preparation of (2,6-iPr2-Ph)N=CMeCMe=N(2-C(=O)NHMe-6-iPr-Ph) (4d) yielded the corresponding 1,2-dihydroquinazolinone derivative 4d′ formed by nucleophilic attack of the amide nitrogen at the proximal imine carbon. 4a and 4b react with (cod)PdMeCl to yield square planar (α-diimine)PdMeCl complexes 5a,a′ and 5b,b′, respectively, which exist as two isomers that differ in the orientation (trans/cis) of the Pd-Me ligand and the amide-substituted arylimine unit. 4c reacts with (MeCN)2PdCl2 and (cod)PdMeCl to yield (4c)PdCl2 (6c-anti,syn) and (4c)PdMeCl (5c-anti,syn), which exhibit anti/syn isomerism due to hindered rotation of the Caryl-N bonds. In the solid state, the amide oxygen atoms in 6c-anti and 5c-syn engage in hydrogen bonding with cocrystallized CH2Cl2 solvent molecules. 4d′ reacts with (MeCN)2PdCl2 via ring-opening metalation to afford the α-diimine complex (4d)PdCl2 (6d). Transmetalation of 6d with SnMe4 yields (4d)PdMeCl (5d,d′) as a mixture of trans and cis isomers. The reaction of 5d,d′ with AgOAc yields (4d)PdMe(OAc) (7d) as a single isomer in which the Pd-Me group is trans to the amide-functionalized arylimine unit. 5d, 6d, and 7d exhibit intramolecular N-H···Cl and N-H···O hydrogen bonding interactions involving the amide NH units. The reactions of 5a,a′, 5c-anti, and 5d,d′ with AgSbF6 in the presence of pyrazole yield the corresponding (α-diimine)PdMe(pz)+SbF6- salts (8a,c,d; pz = pyrazole), which exhibit an intramolecular hydrogen bond between the amide oxygen and the pyrazole NH unit. 8a,c,d undergo partial dissociation of pyrazole in CD3CN solution to generate the corresponding CD3CN complexes 9a,c,d. The non-hydrogen-bonded complex {(2,6-iPr2-Ph)N=CMeCMe=N(2,6-iPr2-Ph)}PdMe(pz)+SbF6- (8e) and its pyrazole dissociation product {(2,6-iPr2-Ph)N=CMeCMe=N(2,6-iPr2-Ph)}PdMe(CD3CN)+SbF6- (9e) were generated in a similar fashion. The pyrazole dissociation constants, Keq = [(α-diimine)PdMe(CD3CN)+] × [pz] × [(α-diimine)PdMe(pz)+]-1, vary in the order 8e > 8d > 8a > 8c, span more than 2 orders of magnitude, and reflect the enhancement of pyrazole binding in 8a,c,d by amide-pyrazole hydrogen bonding. The intramolecular hydrogen bonding in 8c strengthens pyrazole binding by a factor of ca. 120 (i.e., ΔΔG = 2.8(1) kcal mol-1) relative to the case of 8e.
Zhai, Feng,Jordan, Richard F.
supporting information
p. 7176 - 7192
(2015/08/19)

PROCESS TO PREPARE 3-METHYL-2-NITROBENZOIC ACID BY AIR OXIDATION
A method for preparing 3-methyl-2-nitrobenzoic acid is disclosed wherein 1, 3 -dimethyl-2-nitrobenzene is combined with an oxidation catalayst in the presence of an oxygen source and an initiator, provided that less than 99% of the 1,3 -dimethyl-2- nitrobenzene is oxidized. A method for preparing compounds of Formula 7 and Formula 11 is also disclosed wherein the method is characterized by using 3-methyl-2-nitrobenzoic acid as prepared by the method disclosed above. wherein R1 is C1-C7 alkyl, C3-C6 cycloalkyl or C4-C7 alkylcycloalkyl
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Page/Page column 40; 41; 42

(2016/01/30)

AZAQUINAZOLINE CARBOXAMIDE DERIVATIVES
Novel azaquinazoline carboxamide derivatives of formula (I) wherein W1, W2, W3, W4, R1, R2, R3 and m which are defined above, are p70S6K inhibitor, and can be employed, inter alia, for the treatment of hyperproliferative disorders.
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Page/Page column 43; 49; 50

(2014/06/23)

SYNTHESES OF N-HETEROCYCLIC CARBENES AND INTERMEDIATES THEREFOR
A method of preparing a 2,6 disubstituted anilines includes, reacting a 2-amino isophtha!ic acid diester with sufficient Grignard reagent R2CH2MgX to form the corresponding diol product, dehydrating the diol product to the corresponding dialkene; and hydrogenating the diol product to form the corresponding aniline. The 2,6 disubstituted anilines can be used to produce N-Heterocyciic Carbenes (NHCs). The NHCs can find application in various fields such as organic synthesis, catalysis and macromolecular chemistry. Palladium catalysts containing the NHCs are also described.
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Page/Page column 22; 23

(2014/07/23)

Inclusion complex containing epoxy resin composition for semiconductor encapsulation
The invention is an epoxy resin composition for sealing a semiconductor, including (A) an epoxy resin and (B) a clathrate complex. The clathrate complex is one of (b1) an aromatic carboxylic acid compound, and (b2) at least one imidazole compound represented by formula (II): wherein R2 represents a hydrogen atom, C1-C10 alkyl group, phenyl group, benzyl group or cyanoethyl group, and R3 to R5 represent a hydrogen atom, nitro group, halogen atom, C1-C20 alkyl group, phenyl group, benzyl group, hydroxymethyl group or C1-C20 acyl group. The composition has improved storage stability, retains flowability when sealing, and achieves an effective curing rate applicable for sealing delicate semiconductors.
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(2014/03/21)

Large yet flexible N-heterocyclic carbene ligands for palladium catalysis
A straightforward and scalable eight-step synthesis of new N-heterocyclic carbenes (NHCs) has been developed from inexpensive and readily available 2-nitro-m-xylene. This process allows for the preparation of a novel class of NHCs coined ITent ("Tent" for "tentacular") of which the well-known IMes (N,N′-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene), IPr (N,N′-bis(2,6-di(2-propyl)phenyl)imidazol-2-ylidene) and IPent (N,N′-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene) NHCs are the simplest and already known congeners. The synthetic route was successfully used for the preparation of three members of the ITent family: IPent (N,N′-bis(2,6- di(3-pentyl)phenyl)imidazol-2-ylidene), IHept (N,N′-bis(2,6-di(4-heptyl) phenyl)imidazol-2-ylidene) and INon (N,N′-bis(2,6-di(5-nonyl)phenyl) imidazol-2-ylidene). The electronic and steric properties of each NHC were studied through the preparation of both nickel and palladium complexes. Finally the effect of these new ITent ligands in Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-couplings was investigated. Tentacular NHCs: A straightforward, scalable eight-step synthesis of N-heterocyclic carbenes (NHCs) has been developed using inexpensive and readily available 2-nitro-m-xylene, allowing the preparation of a class of NHCs designated ITent ("Tent" for "tentacular"). The electronic and steric properties of each NHC were studied through the preparation of both nickel and palladium complexes, and the effect of these new ITent ligands in Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-couplings was investigated.
Meiries, Sebastien,Le Duc, Gaetan,Chartoire, Anthony,Collado, Alba,Speck, Klaus,Arachchige, Kasun S. Athukorala,Slawin, Alexandra M. Z.,Nolan, Steven P.
supporting information
p. 17358 - 17368
(2014/01/06)

Photodegradable macromers and hydrogels for live cell encapsulation and release
Hydrogel scaffolds are commonly used as 3D carriers for cells because their properties can be tailored to match natural extracellular matrix. Hydrogels may be used in tissue engineering and regenerative medicine to deliver therapeutic cells to injured or diseased tissue through controlled degradation. Hydrolysis and enzymolysis are the two most common mechanisms employed for hydrogel degradation, but neither allows sequential or staged release of cells. In contrast, photodegradation allows external real-time spatial and temporal control over hydrogel degradation, and allows for staged and sequential release of cells. We synthesized and characterized a series of macromers incorporating photodegradbale ortho-nitrobenzyl (o-NB) groups in the macromer backbone. We formed hydrogels from these macromers via redox polymerization and quantified the apparent rate constants of degradation (kapp) of each via photorheology at 370 nm, 10 mW/cm2. Decreasing the number of aryl ethers on the o-NB group increases kapp, and changing the functionality from primary to seconday at the benzylic site dramatically increases kapp. Human mesenchymal stem cells (hMSCs) survive encapsulation in the hydrogels (90% viability postencapsulation). By exploiting the differences in reactivity of two different o-NB linkers, we quantitatively demonstrate the biased release of one stem cell population (green-fluoroescent protein expressing hMSCs) over another (red-fluorescent protein expressing hMSCs).
Griffin, Donald R.,Kasko, Andrea M.
supporting information; experimental part
p. 13103 - 13107
(2012/10/07)

Liquid-crystalline polymorphism of symmetrical azobananas: Bis(4-(4-alkylphenyl)azophenyl) 2-nitroisophtalates
In this paper we present a series of novel compounds, bis(4-(4-alkylphenyl) azophenyl) 2-nitroisophtalates, which exhibit nematic and banana-type liquidcrystalline phases. The alkyl chain length varies from 1 to 18 carbons. The first ten members of this series exhibit nematic phase. The last eleven compounds exhibit banana-type liquid crystalline phases. The propyl and pentyl derivatives have extra second type of banana mesophase. Copyright Taylor & Francis Group, LLC.
Zygadlo,Dardas,Nowicka,Hofmann,Galewski
experimental part
p. 283 - 291
(2011/08/02)

A lockable light-driven molecular shuttle with a fluorescent signal
A turn on! A lockable photodriven molecular shuttle is based on a [2]rotaxane that consists of an α-cyclodextrin threaded by a stilbene derivative. The fluorescent signals originate from the naphthalimide stopper and indicate the position of the shuttle. Once unlocked, the device can be turned on by irradiation at 335 nm and turned off by irradiation at 280 nm. The shuttle can be locked or unlocked by the addition acid or alkali, respectively (see picture).
Wang, Qiao-Chun,Qu, Da-Hui,Ren, Jun,Chen, Kongchang,Tian, He
p. 2661 - 2665
(2007/10/03)

General acid catalysis in the enolization of acetone
We have used iodometry to study the enolization of acetone in water catalyzed by a series of general acids, comprised of hydrochloric acid, methanesulfonic acid, 24 aliphatic monocarboxylic acids, nine aromatic monocarboxylic acids, eight aiphatic dicarboxylic acids, and 20 monoanions of dicarboxylic acids.The log k-pK profile for unbuffered solutions of strong and moderately strong acids shows a maximum near pK ca. 0.The Broensted α value for a set of eight aliphatic monocarboxylic acids in which effects of bulk, charge, and polarizability are at a minimum is 0.56.Steric effects, probably augmented by polarizability effects in some cases, cause positive deviations from the Broensted line drawn with respect to these standard acids.Anionic carboxylic acids are also more reactive than would be predicted from their equilibrium acid strengths, whereas cationic acids tend to be less reactive.Using D2O as solvent has only a small effect on the rate of carboxylic acid catalysis.Using acetone-d6 gives values of kH/kD in the range of 7.0-8.0 at 25 deg C, values consistent with proton or deuteron being transferred between two bases of comparable strength, the carboxylate anion and the enol form of acetone.Key words: general acid catalysis, enolization, Broensted relation, steric effects, deuterium isotope effects.
Shelly, Kevin P.,Venimadhavan, S.,Nagarajan, K.,Stewart, Ross
p. 1274 - 1282
(2007/10/02)

o-Nitroaniline Derivatives. Part 11. 4- and 7-Amino-1H-benzimidazole 3-Oxides
Of the two title compounds, the 4-amino isomer (1a) is easily obtained, either by reduction of the corresponding nitro compound, or in a five-step sequence from 2-nitro-1,3-phenylenediamine.The 7-amino isomer (1d) cannot be obtained by strictly analogous routes but it may be prepared in four steps from 2',3'-dinitroacetanilide.Attempts to cyanomethylate monoacylated 3-nitro-1,2-phenylenediamines (8) lead to 1-acyl-2,3-dihydro-4-nitrobenzimidazoles (10).
Harvey, Ian W.,McFarlane Michael D.,Moody, David J.,Smith, David M.
p. 1939 - 1944
(2007/10/02)

Stepwise Proton Transfer in the Acid-catalysed Hydrolysis of 3,1-Benzoxazin-4-ones: Electrostatic or hydrogen-bond Stabilisation of the Conjugate Acid
The hydrolysis of 3,1-benzoxazin-4-ones is catalyzed by buffer acids and by intramolecular carboxylic acid groups suitably placed on the heterocyclic nucleus.Small or inverse deuterium oxide solvent isotope effects on the acid catalytic terms are consistent with both inter- and intra-molecular acid catalyses proceeding through a preequilibrum protonation mechanism.Proton transfer to the N-1 position concerted with attack at C-2 is not expected because the N-1 protonated 3,1-benzoxazin-4-one is a relatively stable species.The function of the 8-carboxy-anion in the catalysed ring hydrolysis of 8-carboxy-3,1-benzoxazin-4-one is to stabilise the protonated nitrogen (N-1) by electrostatic or hydrogen-bonding interaction.
D'Rozario, A. Peter,Greig, Derek J.,Hudson, Robert F.,Williams, Andrew
p. 590 - 596
(2007/10/02)