10424-29-0Relevant academic research and scientific papers
Cu/PCy3-Catalyzed Formal Carbene Insertion into Electron-Deficient C?H Bonds
Ren, Yuan-Yuan,Mao, Hong-Xiang,Hu, Meng-Yang,Zhu, Shou-Fei,Zhou, Qi-Lin
, p. 4267 - 4271 (2020)
A carbene insertion into electron-deficient C?H bonds of 1,3-diesters, β-ketoesters, β-ketonitriles, and malononitriles was realized by using CuCN/PCy3 as the catalyst. The reaction provides a straightforward approach to the synthetically important multi-substituted succinic acid derivatives. A plausible reaction mechanism with cyclopropanation/ring opening as key steps was proposed based on control experiments.
Enamines; 45. A New Simple Synthesis of 2-Phenylsuccinic Acids
Rossi, Elisabetta,Sassano, Silvia,Stradi, Riccardo
, p. 765 - 766 (1986)
A simple route to 2-phenylsuccinic acids consists of the reaction of 1,1-dimorpholinoethene with β-nitrostyrenes at room temperature and hydrolysis of the 1:1 adduct thus obtained with hydrochloric acid.The method affords good overall yields of 2-phenylsuccinic acids.
Discovery, stereospecific characterization and peripheral modification of 1-(pyrrolidin-1-ylmethyl)-2-[(6-chloro-3-oxo-indan)-formyl]-1,2,3,4-tetrahydroisoquinolines as novel selective κ opioid receptor agonists
Gan, Zong-Jie,Wang, Yu-Hua,Xu, Yun-Gen,Guo, Ting,Wang, Jun,Song, Qiao,Xu, Xue-Jun,Hu, Shi-Yuan,Wang, Yu-Jun,Wang, De-Chuan,Sun, De-Zhu,Zhang, Di,Xi, Tao,Li, Hao-Dong,Zhang, Hai-Bo,Hang, Tai-Jun,Lu, Hong-Guo,Liu, Jing-Gen
, p. 5656 - 5673 (2015)
A novel series of 1-(pyrrolidin-1-ylmethyl)-2-[(3-oxo-indan)-formyl]-1,2,3,4-tetrahydroisoquinoline derivatives maj-3a-maj-3u were synthesized and evaluated in vitro for their binding affinity at κ-opioid receptors. Maj-3c displayed the highest affinity for κ-opioid receptors (Ki = 0.033 nM) among all the compounds evaluated. Furthermore, all four stereoisomers of compound 3c were prepared, and (1S,18S)-3c was identified as the most potent (Ki = 0.0059 nM) κ-opioid receptor agonist among the four stereoisomers. Maj-3c produced significant antinociception (ED50 = 0.000406 mg kg-1) compared to U-50,488H and original BRL 52580 in the acetic acid writhing assay, but its strong sedative effect (ED50 = 0.000568 mg kg-1) observed in the mouse rotation test reduced its druggability. To minimize the central nervous system side effects, a series of hydroxyl-containing analogs of maj-3c were synthesized, and maj-11a was found to be a potent κ-opioid receptor agonist (Ki = 35.13 nM). More importantly, the dose for the sedative effect (ED50 = 9.29 mg kg-1) of maj-11a was significantly higher than its analgesic dose (ED50 = 0.392 mg kg-1), which made it a promising peripheral analgesic candidate compound with weak sedative side effects.
Photoredox Activation of Formate Salts: Hydrocarboxylation of Alkenes via Carboxyl Group Transfer
Huang, Yan,Hou, Jing,Zhan, Le-Wu,Zhang, Qian,Tang, Wan-Ying,Li, Bin-Dong
, p. 15004 - 15012 (2021/12/14)
A photoredox activation mode of formate salts for carboxylation was developed. Using a formate salt as the reductant, carbonyl source, and hydrogen atom transfer reagent, a wide range of alkenes can be converted into acid products via a carboxyl group tra
Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins
Alkayal, Anas,Buckley, Benjamin R.,Malkov, Andrei V.,Montanaro, Stephanie,Tabas, Volodymyr,Wright, Iain A.
supporting information, (2020/02/13)
The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.
Stereoselective One-Pot Synthesis of cis-1,2-Dicyanoalkenes from 1,1-Bis(benzenesulfonyl)alkenes and KCN
Zhang, Yue,Wei, Yi,Li, Shen,Ma, Jun-An
, p. 199 - 203 (2019/01/04)
An efficient synthesis of cis-1,2-dicyanoalkenes by the reaction of 1,1-bis(benzenesulfonyl)alkenes with KCN was developed. This reaction was conducted in the presence of tetrabutylammonium bromide and NH4Cl/K3PO4 under phase-transfer conditions. A series of cis-1,2-dicyanoalkenes were obtained in good to high yields. Further transformation of the obtained product allows for access to imide and dicarboxylic acid compounds.
Method for synthesizing succinic acid compounds
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Paragraph 0028-0036; 0040, (2019/08/01)
The invention provides a method for synthesizing succinic acid compounds. The method specifically comprises the following steps: adding a substrate, a photocatalyst and an alkali into a reaction tube,adding a reducing agent and a solvent under the atmosphere of CO2, conducting reacting under the irradiation of visible light, carrying out quenching treatment after the raw materials react completely, and then conducting separating and purifying to obtain a dicarboxylated product of olefin, namely a succinic acid compound. The photocatalyst is 4CzIPN or Ir[(ppy)2(dtbppy)]PF6 and the like, and the reaction substrate comprises 1,1-diaryl ethylene, a monoaryl substituted olefin compound, an acrylate compound and allene. According to the scheme provided by the invention, the reaction conditionsare mild, the applicability of the reaction substrate is wide, and the yield is basically not influenced under the condition that the reaction substrate is amplified to the gram scale; and meanwhile,the invention overcomes the defects of high toxicity of reagents and harsh reaction conditions in the prior art, and has a good industrial application prospect.
Preparation method and application of tetrahydroisoquinoline derivative
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Paragraph 0035-0038, (2019/03/08)
The invention discloses a preparation method of a tetrahydroisoquinoline derivative. The tetrahydroisoquinoline derivative is prepared by subjecting 1-(tetrapyrrolidin-1-yl)-1,2,3,4-tetrahydroisoquinoline and 2,3-dihydro-indene-3-one-1-carboxylic acid to condensation. Process conditions are optimized so that preparation steps are simplified. Agents used in the preparation are pollution free. The prepared tetrahydroisoquinoline derivative 1-(tetrapyrrolidin-1-methyl)-2-(2,3-dihydro-indene-3-one-1-carbonyl)-1,2,3,4-tetrahydroisoquinoline can provide good calming effect against neuropathic pain.The tetrahydroisoquinoline derivative has high medical value in drug compositions for pain treatment and in replacing dependent analgesics, such as morphine.
Direct β-Selective Hydrocarboxylation of Styrenes with CO2 Enabled by Continuous Flow Photoredox Catalysis
Seo, Hyowon,Liu, Aofei,Jamison, Timothy F.
supporting information, p. 13969 - 13972 (2017/10/17)
The direct β-selective hydrocarboxylation of styrenes under atmospheric pressure of CO2 has been developed using photoredox catalysis in continuous flow. The scope of this methodology was demonstrated with a range of functionalized terminal styrenes, as well as α-substituted and β-substituted styrenes.
DERIVATIVES OF 2-PYRIDIN-2-YL-PYRAZOL-3(2H)-ONE, PREPARATION AND THERAPEUTIC USE THEREOF AS HIF ACTIVATORS
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, (2011/12/13)
The present invention relates to novel substituted dihydropyrazolone derivatives, to their preparation and to their therapeutic use as activators of the transcription factor HIF.
