(Z)-2-phenyl-3-(4-(trifluoromethyl)phenyl)acrylonitrile | 147728-28-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-2-phenyl-3-(4-(trifluoromethyl)phenyl)acrylonitrile
• 英文别名: (Z)-2-phenyl-3-[4-(trifluoromethyl)phenyl]acrylonitrile；Z-2-phenyl-3-(4-trifluoromethylphenyl)acrylonitrile；alpha-Phenyl-4-(trifluoromethyl)-cis-cinnamonitrile；(Z)-2-phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-enenitrile
• CAS: 147728-28-7
• 化学式: C₁₆H₁₀F₃N
• 分子量: 273.257
• InChiKey: WMJSLIYHNRHXRU-GXDHUFHOSA-N

物化性质

• 熔点：
  112-114 °C
• 沸点：
  336.3±42.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(三氟甲基)苄醇 、 苯乙腈 在 C₃₂H₂₅Cl₂N₆O₂Rh₂⁽¹⁺⁾*Cl^(1-) 、 氧气 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以78%的产率得到(Z)-2-phenyl-3-(4-(trifluoromethyl)phenyl)acrylonitrile
  参考文献：
  名称：

  大气控制的化学选择性：铑催化的醇烷基化和烷基化

  摘要：

  通过简单地控制反应气氛，已经开发了烷基腈与醇的化学选择性烷基化和烯化。双核铑配合物可通过氢借入途径催化氩气下的烷基化反应，而需氧脱氢则可催化氧气下的烯化反应。展示了广泛的底物范围，可以合成一些重要的有机结构单元。机理研究表明，烷基化产物可通过氢化铑将烯烃中间体共轭还原而形成，而烯烃产物的形成可能是由于氢化铑络合物与分子氧的氧化所致。

  DOI：

  10.1002/chem.201704037

文献信息

• Atmosphere-Controlled Chemoselectivity: Rhodium-Catalyzed Alkylation and Olefination of Alkylnitriles with Alcohols
  作者：Junjun Li、Yuxuan Liu、Weijun Tang、Dong Xue、Chaoqun Li、Jianliang Xiao、Chao Wang

  DOI：10.1002/chem.201704037

  日期：2017.10.17

  The chemoselective alkylation and olefination of alkylnitriles with alcohols have been developed by simply controlling the reaction atmosphere. A binuclear rhodium complex catalyzes the alkylation reaction under argon through a hydrogen‐borrowing pathway and the olefination reaction under oxygen through aerobic dehydrogenation. Broad substrate scope is demonstrated, permitting the synthesis of some

  通过简单地控制反应气氛，已经开发了烷基腈与醇的化学选择性烷基化和烯化。双核铑配合物可通过氢借入途径催化氩气下的烷基化反应，而需氧脱氢则可催化氧气下的烯化反应。展示了广泛的底物范围，可以合成一些重要的有机结构单元。机理研究表明，烷基化产物可通过氢化铑将烯烃中间体共轭还原而形成，而烯烃产物的形成可能是由于氢化铑络合物与分子氧的氧化所致。
• Manganese Catalyzed α-Olefination of Nitriles by Primary Alcohols
  作者：Subrata Chakraborty、Uttam Kumar Das、Yehoshoa Ben-David、David Milstein

  DOI：10.1021/jacs.7b06993

  日期：2017.8.30

  Catalytic α-olefination of nitriles using primary alcohols, via dehydrogenative coupling of alcohols with nitriles, is presented. The reaction is catalyzed by a pincer complex of an earth-abundant metal (manganese), in the absence of any additives, base, or hydrogen acceptor, liberating dihydrogen and water as the only byproducts.

  介绍了通过醇与腈的脱氢偶联，使用伯醇催化 α-烯化腈。该反应由富含地球的金属（锰）的钳状络合物催化，不存在任何添加剂、碱或氢受体，释放出氢和水作为唯一的副产物。
• (<i>Z</i>)-2-(2-Bromophenyl)-3-{[4-(1-methyl-piperazine)amino]phenyl}acrylonitrile (DG172): An Orally Bioavailable PPARβ/δ-Selective Ligand with Inverse Agonistic Properties
  作者：Sonja Lieber、Frithjof Scheer、Wolfgang Meissner、Simone Naruhn、Till Adhikary、Sabine Müller-Brüsselbach、Wibke E. Diederich、Rolf Müller

  DOI：10.1021/jm2017122

  日期：2012.3.22

  The ligand-regulated nuclear receptor peroxisome proliferator-activated receptor beta/delta (PPAR beta/delta) is a potential pharmacological target due to its role in disease-related biological processes. We used TR-FRET-based competitive ligand binding and coregulator interaction assays to screen 2693 compounds of the Open Chemical Repository of the NCl/NIH Developmental Therapeutics Program for inhibitory PPAR beta/delta ligands. One compound, (Z)-3-(4-dimethylamino-phenyl)-2-phenyl-acrylonitrile, was used for a systematic SAR study. This led to the design of derivative 37, (Z)-2-(2-bromopheny1)-3-[4-(1-methyl-piperazine)amino]phenyl}acrylonitrile (DG172), a novel PPAR beta/delta-selective ligand showing high binding affinity (IC50 = 27 nM) and potent inverse agonistic properties. 37 selectively inhibited the agonist-induced activity of PPAR beta/delta, enhanced transcriptional corepressor recruitment, and down-regulated transcription of the PPAR beta/delta target gene Angptl4 in mouse myoblasts (IC50 = 9.5 nM). Importantly, 37 was bioavailable after oral application to mice with peak plasma levels in the concentration range of its maximal inhibitory potency, suggesting that 37 will be an invaluable tool to elucidate the functions and therapeutic potential of PPAR beta/delta.
• Solvent-free condensation of arylacetonitrile with aldehydes
  作者：Régis Guillot、André Loupy、Abdelkrim Meddour、Michèle Pellet、Alain Petit

  DOI：10.1016/j.tet.2005.07.040

  日期：2005.10

  The condensation of a series of arylacetonitriles with aldehydes can be carried out by mixing equivalent amounts of reagents with neat powdered KOH at room temperature for 3-60 min depending on the aldehyde steric hindrance. At higher temperature (110 degrees C), yields were generally higher and purity increased within very short reaction times (1-5 min). With pentamethylphenylacetonitrile, a phase transfer agent was necessary to give a satisfactory yield. (c) 2005 Elsevier Ltd. All rights reserved.
• US5792568A
  申请人：——

  公开号：US5792568A

  公开（公告）日：1998-08-11