(E)-3-(4-chlorophenyl)-N-phenethylacrylamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(4-chlorophenyl)-N-phenethylacrylamide
• 英文别名: (2E)-3-(4-chlorophenyl)-N-(2-phenylethyl)prop-2-enamide；(E)-3-(4-chlorophenyl)-N-(2-phenylethyl)prop-2-enamide
• 化学式: C₁₇H₁₆ClNO
• 分子量: 285.773
• InChiKey: UIVHFGGSZLLTNW-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对氯肉桂酸 在 氯化亚砜 、 三乙胺 作用下， 生成 (E)-3-(4-chlorophenyl)-N-phenethylacrylamide
  参考文献：
  名称：

  N-(2-(4-hydroxyphenyl)ethyl)-4-chlorocinnamide: A novel antagonist at the 1a/2B NMDA receptor subtype

  摘要：

  A series of N-(2-phenethyl)cinnamides was synthesized and assayed for antagonism at three N-methyl-D-asparate (NMDA) receptor subtypes (NR1A/2A-C). N-(2-(4-hydroxyphenyl)ethyl)-4-chlorocinnamide (6) was identified as a highly potent and selective antagonist of the NR1A/2B subtype. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)10215-3

文献信息

• Rapid access to cinnamamides and piper amides <i>via</i> three component coupling of arylaldehydes, amines, and Meldrum's acid
  作者：Santanu Ghosh、Chandan K. Jana

  DOI：10.1039/c9gc02937k

  日期：——

  A practical method for the synthesis of cinnamamides and piper amides via a conceptually novel three component reaction of aldehydes, amines and Meldrum's acid has been reported. The reaction proceeds under operationally simple conditions without the aid of coupling reagents, oxidants, or catalysts, which are essential for the preparation of cinnamamides/piper amides via known methods. The formation

  已经报道了通过概念上新颖的醛，胺和梅德鲁姆酸的三组分反应合成肉桂酰胺和哌啶酰胺的实用方法。该反应在操作简单的条件下进行，无需借助偶联剂，氧化剂或催化剂，而偶联剂，氧化剂或催化剂是通过已知方法制备肉桂酰胺/哌酰胺所必需的。避免了通常由于使用偶联剂，氧化剂或催化剂而产生的不希望有的化学废物，从而使该反应更经济。
• Efficient Syntheses of β-Amino-<i>N</i>-acylbenzotriazoles and Cinnamides through Regioselective 1,4- or 1,2-Addition of Amines to<i>N</i>-Cinnamoylbenzotriazoles
  作者：Xiaoxia Wang、Xuefei Zou、Jian Li、Qinghong Hu

  DOI：10.1055/s-2005-921918

  日期：——

  Amines react with N-cinnamoylbenzotriazoles to afford either β-amino-N-acylbenzotriazoles or cinnamides depending on the structure of the amines. Aromatic amines react with N-­cinnamoylbenzotriazoles via 1,4-addition to give β-amino-N-acylbenzotriazoles in good yields. For o-phenylenediamine, the 1,4-addition products were further acylated to provide a facile route to substituted 1,3,4,5-tetrahydro-1,5-benzodiazepine-2-ones. Ali­phatic amines, however, react exclusively through the 1,2-addition pathway to produce cinnamides in good yields.

  根据胺的结构，胺与 N-肉桂酰基苯并三唑反应可生成δ-氨基-N-酰基苯并三唑或肉桂酰胺。芳香胺与 N-肉桂酰基苯并三唑通过 1,4-加成反应生成δ-氨基-N-酰基苯并三唑，产率高。对于邻苯二胺，1,4-加成产物可进一步酰化，从而为获得取代的 1,3,4,5-四氢-1,5-苯并二氮杂卓-2-酮提供了便捷的途径。然而，脂肪族胺只能通过 1,2-加成途径进行反应，从而以良好的产率生成肉桂酰胺。
• Features and applications of reactions of α,β-unsaturated N-acylbenzotriazoles with amino compounds
  作者：Xiaoxia Wang、Zhifang Li、Xiangming Zhu、Hui Mao、Xuefei Zou、Lichun Kong、Xinsheng Li

  DOI：10.1016/j.tet.2008.04.054

  日期：2008.6

  triethylamine, α,β-unsaturated N-acylbenzotriazoles reacted with amino compounds in a variety of ways. Thus, N-cinnamoylbenzotriazoles reacting with aromatic amines afforded novel addition products β-benzotriazolyl amides 3, which might be normally formed from the alternative but unknown 1,4-addition of benzotriazole to N-cinnamoylamides. The type 3 compounds could also result from the reaction between

  在三乙胺的促进下，α，β-不饱和N-酰基苯并三唑以多种方式与氨基化合物反应。因此，N-肉桂酰基苯并三唑与芳族胺反应提供了新的加成产物β-苯并三唑基酰胺3，其通常可以由苯并三唑与N-肉桂酰基酰胺的1,4-取代但未知的加成反应形成。N-巴豆酰苯并三唑与脂族胺之间的反应也可能产生3型化合物。但是，在α，β-不饱和脂肪族N-酰基苯并三唑与芳族胺之间可能会发生正常的1,4-加成反应，从而导致β-氨基N-酰基苯并三唑4丰产。此外，脂族胺与N-肉桂酰基苯并三唑的独家1,2-加成反应使肉桂酸酯5的收率极高。因此，三种可能的途径提出合理化化合物的形成3 - 5。最后，以邻苯二胺和邻氨基苯硫酚为底物，可以同时发生α，β-不饱和N-酰基苯并三唑的1,4-和1,2-加成反应，相应的杂环1,5-苯并二氮杂-2-分别构建1个和1，5-苯并硫氮杂-4-酮。
• Structure−Activity Relationship of <i>N</i>-(Phenylalkyl)cinnamides as Novel NR2B Subtype-Selective NMDA Receptor Antagonists
  作者：Amir P. Tamiz、Sui Xiong Cai、Zhang-Lin Zhou、Po-Wai Yuen、Robert M. Schelkun、Edward R. Whittemore、Eckard Weber、Richard M. Woodward、John F. W. Keana

  DOI：10.1021/jm990199u

  日期：1999.8.1

  A novel series of N-(phenylalkyl)cinnamides related to N-(4-phenylbutyl)-3,4-dihydroxy-beta-cyanocinnamide (6, an EGFR-K inhibitor with high antiproliferative activity) was synthesized and tested for antagonism at N-methyl-D-aspartate (NMDA) receptor subtypes. Potency and subunit selectivity were assayed by electrical recordings in Xenopus oocytes expressing three binary combinations of cloned rat NMDA receptor subunits: NR1A expressed in combination with either NR2A, NR2B, or NR2C. The N-(phenylalkyl)cinnamides are selective antagonists of NR1A/2B receptors. Assayed under steady-state conditions, N-(4-phenylbutyl)-4-hydroxycinnamide (16) has an IC50 value of 77 nM and >1000-fold selectivity with respect to NR1A/2A and NR1A/2C receptors. Potency at alpha(1) adrenergic receptors is low for the four cinnamides tested. Inhibition of NR1A/2B receptors does not correlate with EGFR and ErbB2/neu tyrosine kinase inhibitor activity. The N-(phenylalkyl)cinnamide series we describe provides a novel and structurally diverse framework for designing new NR2B-selective NMDA antagonists as potential CNS therapeutics.