- Photoinduced Carbon Tetrabromide Initiated Aerobic Oxidation of Substituted Toluenes to Carboxylic Acids
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A mild and metal-free procedure is reported for the aerobic oxidation of substituted toluenes to carboxylic acids by using CBr 4 as initiator under irradiation from a 400 nm blue light-emitting diode.
- Li, Xiaoqing,Xu, Xiangsheng,Yan, Xiaoyu,Yan, Xinhuan,Zhang, Guofu,Zheng, Kun
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p. 272 - 274
(2020/02/18)
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- Synthesis method of benzoic acid compounds
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The invention discloses a photocatalytic oxidation synthesis method of benzoic acid compounds, and the photocatalytic oxidation synthesis method comprises the following specific steps: mixing and dissolving toluene compounds and a catalyst in a solvent, reacting for 24-60h in the presence of an oxidant under the conditions of 350-460 nm LED illumination and a temperature of 20-80 DEG C, and performing post-treatment on the reaction liquid to obtain the benzoic acid compounds. The photocatalytic oxidation synthesis method has the advantages of no need of metal catalysts, simple operation and mild reaction conditions; oxygen is used as an oxidant, and the photocatalytic oxidation synthesis method has high atom economy, cheap reagent and environmental protection. The photocatalytic oxidationsynthesis method has good substrate applicability, and various substituents can realize the synthesis of corresponding benzoic acid compounds.
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Paragraph 0146; 0147; 0148; 0149
(2019/12/25)
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- METHOD FOR PRODUCING 2-HALOGENATED BENZOIC ACIDS
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The purpose of the present invention is to provide a method for producing 2-halogenated benzoic acids, the method imparting high regioselectivity (high selectivity) and having a shorter reaction time than does the conventional reaction. This method for producing 2-halogenated benzoic acids, in order to achieve the above purpose, is characterized in that benzoic acids and a halogenating agent are reacted in the presence of an alkaline compound, making it possible to highly selectively obtain 2-halogenated benzoic acids.
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Paragraph 0064
(2018/04/20)
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- Zn-Catalyzed Enantio- and Diastereoselective Formal [4 + 2] Cycloaddition Involving Two Electron-Deficient Partners: Asymmetric Synthesis of Piperidines from 1-Azadienes and Nitro-Alkenes
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We report a catalytic asymmetric synthesis of piperidines through [4 + 2] cycloaddition of 1-azadienes and nitro-alkenes. The reaction uses earth abundant Zn as catalyst and is highly diastereo- and regioselective. A novel BOPA ligand (F-BOPA) confers high reactivity and enantioselectivity in the process. The presence of ortho substitution on the arenes adjacent to the bis(oxazolines) was found to be particularly impactful, due to limiting the undesired coordination of 1-azadiene to the Lewis acid and thus allowing the reaction to be carried out at lower temperature. A series of secondary kinetic isotope effect studies using a range of ligands implicates a stepwise mechanism for the transformation, involving an initial Michael-type addition of the imine to the nitro-alkene followed by a cyclization event. The stepwise mechanism obviates the electronic requirement inherent to a concerted mechanism, explaining the successful cycloaddition between two electron-deficient partners. (Chemical Equation Presented).
- Chu, John C. K.,Dalton, Derek M.,Rovis, Tomislav
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supporting information
p. 4445 - 4452
(2015/04/14)
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- ENHANCING AUTOPHAGY OR INCREASING LONGEVITY BY ADMINISTRATION OF UROLITHINS OR PRECURSORS THEREOF
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Disclosed are methods, compounds, and compositions useful for increasing autophagy and promoting longevity. The methods, compounds, and compositions relate to urolithins and urolithin precursors and use thereof. Certain urolithins are represented by Formula I, while certain urolithin precursors are represented by Formula IV. The urolithin may be urolithin A, urolithin B, urolithin C, or urolithin D. The urolithin precursor may be ellagic acid or an ellagitannin. The methods include in vivo, ex vivo, and in vitro uses of the compounds and compositions.
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- Impact of electronic modification of the chelating benzylidene ligand in cis-dichloro-configured second-generation olefin metathesis catalysts on their activity
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A series of electronically modified second-generation cis-dichloro ruthenium ester chelating benzylidene complexes was prepared, characterized, and benchmarked in a typical ring-opening metathesis polymerization (ROMP) experiment. The electronic tuning of the parent chelating benzylidene ligand (2-ethyl ester benzylidene) was achieved by substitution at the 4- and 5-positions with electron-withdrawing nitro or electron-donating methoxy groups. The effect of the electronic tuning on the cis-trans isomerization process was studied experimentally and theoretically. Density functional theory calculations clearly revealed the influence of electronic modification on the relative stability between the cis and trans isomers, which is decisive for the activity of the studied compounds as initiators in ROMP.
- Pump, Eva,Poater, Albert,Zirngast, Michaela,Torvisco, Ana,Fischer, Roland,Cavallo, Luigi,Slugovc, Christian
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p. 2806 - 2813
(2014/06/24)
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- Synthesis and structure-activity relationship studies of O-biphenyl-3-yl carbamates as peripherally restricted fatty acid amide hydrolase inhibitors
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The peripherally restricted fatty acid amide hydrolase (FAAH) inhibitor URB937 (3, cyclohexylcarbamic acid 3′-carbamoyl-6-hydroxybiphenyl-3-yl ester) is extruded from the brain and spinal cord by the Abcg2 efflux transporter. Despite its inability to enter the central nervous system (CNS), 3 exerts profound antinociceptive effects in mice and rats, which result from the inhibition of FAAH in peripheral tissues and the consequent enhancement of anandamide signaling at CB1 cannabinoid receptors localized on sensory nerve endings. In the present study, we examined the structure-activity relationships (SAR) for the biphenyl region of compound 3, focusing on the carbamoyl and hydroxyl groups in the distal and proximal phenyl rings. Our SAR studies generated a new series of peripherally restricted FAAH inhibitors and identified compound 35 (cyclohexylcarbamic acid 3′-carbamoyl-5- hydroxybiphenyl-3-yl ester) as the most potent brain-impermeant FAAH inhibitor disclosed to date.
- Moreno-Sanz, Guillermo,Duranti, Andrea,Melzig, Laurin,Fiorelli, Claudio,Ruda, Gian Filippo,Colombano, Giampiero,Mestichelli, Paola,Sanchini, Silvano,Tontini, Andrea,Mor, Marco,Bandiera, Tiziano,Scarpelli, Rita,Tarzia, Giorgio,Piomelli, Daniele
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p. 5917 - 5930
(2013/08/23)
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- SMALL MOLECULE COMPOUNDS FOR STEM CELL DIFFERENTIATION
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Methods and small molecule compounds for stem cell differentiation are provided. One example of a class of compounds that may be used is represented by the compound having the structure IA or IB in the form of free base or a pharmaceutically acceptable salt, hydrate, solvate or N-oxide thereof. R1 is independently hydrogen or (C1-C6)alkyl; R2 is independently hydrogen, (C1-C6)alkyl, aryl, or heteroaryl; R2' is independently hydrogen, (C1-C6)alkyl, CF3 or C2F5; R3 is independently (C1-C6)alkyl, aryl, 2-tetrahydrofuryhnethyl, an aliphatic tertiary amine, or 4-methoxybenzyl; or R2 and R3 may be joined together to form a 5 or 6 member ring lactone; R4 is independently hydrogen, (C1-C6)alkyl, a 2- or 4-R5-substituted aromatic ring selected from a 4-R5-phenyl or a 2-R5-5-pyridyl, aryl, heteroaryl, aliphatic tertiary amine or halogen; and R5, R5', R6, R6', R7, R7' are each independently hydrogen, (C1-C6)alkyl, aryl, optionally substituted phenyl, heteroaryl, a heterocyclic ring, an aliphatic tertiary amine, or halogen.
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Page/Page column 79; 80
(2010/04/25)
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- 5,5'- POSITION LINKED 1,1'- BIPHENYL AXIAL CHIRAL LIGAND AND METHOD FOR PREPARING THE SAME
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The present invention relates to a 5,5′-position linked 1,1′-biphenyl axis chiral ligand in chemical industry field. The present invention incorporates both the central chirality of oxazoline and the axial chirality of diphenyls. Such ligand can be used i
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Page/Page column 4
(2009/07/03)
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- Novel atropisomeric bisphosphine ligands with a bridge across the 5,5′-position of the biphenyl for asymmetric catalysis
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A new type of atropisomeric bisphosphine ligand 2 with a bridge across the 5,5′-position of the biphenyl has been developed. The axial chirality of this type of ligands can be retained by macrocyclic ring strain produced from 5,5′-linkage of the biphenyl
- Wei, Hao,Zhang, Yong Jian,Wang, Feijun,Zhang, Wanbin
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p. 482 - 488
(2008/09/19)
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- Highly enantioselective Pd(II)-catalyzed Wacker-type cyclization of 2-allylphenols by use of bisoxazoline ligands with axis-unfixed biphenyl backbone
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A series of axis-unfixed bisoxazoline ligands with different steric and electronic properties has been synthesized. Due to the different steric interactions, the ligands afforded only one of the two possible diastereomeric Pd(II)-complexes upon metal coor
- Wang, Feijun,Zhang, Yong Jian,Yang, Guoqiang,Zhang, Wanbin
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p. 4179 - 4182
(2008/02/05)
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- Atropisomeric bisoxazoline ligands with a bridge across the 5,5′-position of biphenyl for asymmetric catalysis
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A new family of atropisomeric bisoxazoline ligands 2 with a bridge across the 5,5′-position of biphenyl has been developed. The axial chirality of this type of ligands can be retained by macro-ring strain produced by 5,5′-linkage of biphenyls even without
- Wang, Feijun,Zhang, Yong Jian,Wei, Hao,Zhang, Jiaming,Zhang, Wanbin
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p. 4083 - 4086
(2008/02/03)
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- First general, direct, and regioselective synthesis of substituted methoxybenzoic acids by ortho metalation
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(Chemical Equation Presented) New general methodology of value in aromatic chemistry based on ortho-metalation sites in o-, m-, and p-anisic acids (1-3) (Scheme 1) is described. The metalation can be selectively directed to either of the ortho positions by varying the base, metalation temperature, and exposure times. Metalation of o-anisic acid (1) with s-BuLi/TMEDA in THF at -78°C occurs exclusively in the position adjacente to the carboxylate. On the other hand, a reversal of regioselectivity is observed with n-BuLi/t-BuOK. With LTMP at 0°C, the two directors of m-anisic acid (2) function in concert to direct introduction of the metal between them while n-BuLi/t-BuOK removes preferentially the proton located ortho to the methoxy and para to the carboxylate (H-4). s-BuLi/TMEDA reacts with p-anisic acid (3) exclusively in the vicinity of the carboxylate. According to these methodologies, routes to very simple methoxybenzoic acids with a variety of functionalities that are not easily accessible by other means have been developed (Table 1).
- Nguyen, Thi-Huu,Chau, Nguyet Trang Thanh,Castanet, Anne-Sophie,Nguyen, Kim Phi Phung,Mortier, Jacques
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p. 3419 - 3429
(2008/02/03)
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- Antiestrogenic N-(4-hydroxyphenyl)-N-(1,1,1-trifluoro-2-propyl)-4-hydroxybenzamides: Influence of hydrophobic groups substituted in the ortho-position of the benzamide-fragment on activity
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Experiments are reported here to develop compounds with antiestrogenic and mammary tumor inhibiting properties. Analogues with hydrophobic groups in 2- or 2,6-position of the benzamide-fragment of N-(4-hydroxyphenyl)-N-(1,1,1-trifluoro-2-propyl)-4-hydroxy
- Hartmann,Vom Orde,Schonenberger
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