顺式-4-二甲基氨基肉桂腈 | 31145-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 顺式-4-二甲基氨基肉桂腈
• 中文别名: 顺-4-二甲氨基肉桂腈(含约15反-异构体)
• 英文名称: (Z)-3-(4-dimethylaminophenyl)acrylonitrile
• 英文别名: (Z)-4-(N,N-dimethylamino)cinnamonitrile；(Z)-p-(dimethylamino)cinnamonitrile；4-dimethylamino-cis-cinnamonitrile；4-Dimethylamino-cis-cinnamonitril；4-dimethylaminocinnamonitrile；p-Dimethylamino-cis-zimtsaeure-nitril；cis-4-Dimethylaminocinnamonitrile；(Z)-3-[4-(dimethylamino)phenyl]prop-2-enenitrile
• CAS: 31145-02-5
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: CSCOHKCYDZVRMQ-ARJAWSKDSA-N

物化性质

• 熔点：
  58.0 to 62.0 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-2-cyano-3-(4-(dimethylamino)phenyl)acrylic acid 在 copper(I) oxide 作用下， 生成 顺式-4-二甲基氨基肉桂腈
  参考文献：
  名称：

  Transmission of substituent effects through extended systems—II. Substituted cis and trans cinnamonitriles

  摘要：

  DOI：

  10.1016/0584-8539(82)80001-9

文献信息

• Synthetic studies related to diketopyrrolopyrrole (DPP) pigments. Part 1: The search for alkenyl-DPPs. Unsaturated nitriles in standard DPP syntheses: a novel cyclopenta[c]pyrrolone chromophore
  作者：Colin J.H Morton、Ryan Gilmour、David M Smith、Philip Lightfoot、Alexandra M.Z Slawin、Elizabeth J MacLean

  DOI：10.1016/s0040-4020(02)00443-x

  日期：2002.7

  methacrylonitrile give 4,4-bis(cyanoethyl) and 4,4-bis(2-cyanopropyl) derivatives, and cinnamonitrile, substituted cinnamonitriles and 3-(2-thienyl)acrylonitrile give deep red 3-aryl-5-cyano-4-hydroxy-2H-cyclopenta[c]pyrrol-1-ones. These ambident nucleophiles may undergo N- and either O- or C-alkylation according to the alkylating agent used.

  4,5-二氢-5-氧代-2-苯基吡咯-3-羧酸乙酯的阴离子与丙烯腈和各种二烯的狄尔斯-阿尔德加合物的反应很少产生预期的DPP衍生物。与环己-3-烯腈的反应提供了一个值得注意的例外：所生成的环己烯基-DPP的热解产生了丁二烯和不纯的3-乙烯基-6-苯基-DPP，后者是热不稳定的。当上述阴离子与α，β-不饱和腈反应时，迈克尔加成反应占主导：丙烯腈和甲基丙烯腈产生4,4-双（氰基乙基）和4,4-双（2-氰基丙基）衍生物，以及肉桂腈，取代的肉桂腈和3-（ 2-噻吩基）丙烯腈得到深红色的3-芳基-5-氰基-4-羟基-2 H-环戊[ c ]吡咯-1-酮。这些亲核试剂两可可经历Ñ-和根据所用烷基化剂的O-或C-烷基化。
• A new method for the synthesis of cinnamonitriles by catalytic olefination
  作者：V. G. Nenajdenko、I. V. Golubinskii、O. N. Lenkova、A. V. Shastin、E. S. Balenkova

  DOI：10.1007/s11172-005-0245-0

  日期：2005.1

  Catalytic olefination of hydrazones of aromatic aldehydes with dibromoacetonitrile affords cinnamonitriles.

  芳香醛的肼醇衍生物与二溴乙腈的催化烯化反应可得到肉桂腈。
• Optimization of Chemical Functionalities of Indole-2-carboxamides To Improve Allosteric Parameters for the Cannabinoid Receptor 1 (CB1)
  作者：Leepakshi Khurana、Hamed I. Ali、Teresa Olszewska、Kwang H. Ahn、Aparna Damaraju、Debra A. Kendall、Dai Lu

  DOI：10.1021/jm5000112

  日期：2014.4.10

  5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide (1; ORG27569) is a prototypical allosteric modulator for the cannabinoid type I receptor (CBI). Here, we reveal key structural requirements of indole-2-carboxamides for allosteric modulation of CBI: a critical chain length at the C3-position, an electron withdrawing group at the CS-position, the length of the linker between the amide bond and the phenyl ring B, and the amino substituent on the phenyl ring B. These significantly impact the binding affinity (K-B) and the binding cooperativity (alpha). A potent CB1 allosteric modulator 5-chloro-N-(4(dimethylamino)phenethyl)-3-propyl-1H-indole-2-carboxamide (12d) was identified. It exhibited a K-B of 259.3 nM with a strikingly high binding alpha of 24.5. We also identified 5-chloro-N-(4-(dimethylamino)phenethyl)-3-hexyl-1H-indole-2-carboxamide (120 with a K-B of 89.1 nM, which is among the lowest K-B values obtained for any allosteric modulator of CB1. These positive allosteric modulators of orthosteric agonist binding nonetheless antagonized the agonist-induced G-protein coupling to the CB1 receptor, yet induced beta-arrestin mediated ERK/2 phosphorylation.
• Razus, Alexandra C.; Nitu, Carmen; Tecuceanu, Victorita, Revue Roumaine de Chimie, 2005, vol. 50, # 9-10, p. 729 - 736
  作者：Razus, Alexandra C.、Nitu, Carmen、Tecuceanu, Victorita、Birzan, Liviu

  DOI：——

  日期：——
• Huang, Xian; Pi, Jin-Hong; Huang, Zhi-Zhen, Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 67, # 1-4, p. 177 - 182
  作者：Huang, Xian、Pi, Jin-Hong、Huang, Zhi-Zhen

  DOI：——

  日期：——