(S)-2-phenyl-4-penteneamide | 500721-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-phenyl-4-penteneamide
• 英文别名: (2S)-2-phenylpent-4-enamide
• CAS: 500721-74-4
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: PLJIMCNZIZHJQR-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2-phenyl-4-penteneamide 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 24.0h， 以0.97 g的产率得到(S)-2-phenylpent-4-enenitrile
  参考文献：
  名称：

  Heteroatom-Directed Alkylcyanation of Alkynes

  摘要：

  Alkanenitriles having a heteroatom such as nitrogen, oxygen, and sulfur at the gamma-position are found to add across alkynes stereo- and regioselectively by nickel/Lewis acid catalysis to give highly substituted acrylonitriles. The heteroatom functionalities likely coordinate to the nickel center to make oxidative addition of the C-CN bonds of the alkyl cyanides kinetically favorable, forming a five-membered nickelacycle intermediate and, thus, preventing beta-hydride elimination to allow the alkylcyanation reaction.

  DOI：

  10.1021/ja1017078
• 作为产物：
  描述：

  在 ammonium hydroxide 作用下， 反应 1.5h， 生成 (S)-2-phenyl-4-penteneamide
  参考文献：
  名称：

  A Convenient Synthesis of Chiral β³-Amino Acids

  摘要：

  开发了一种合成手性β3-氨基酸的新方法，其中酸功能团是通过氧化断裂引入的α-烯丙基，该基团由Evans不对称烷基化适当的酸底物引入，而氨基部分则来自原始羧基的酰胺，经过改良的Hofmann重排反应后形成。

  DOI：

  10.1055/s-2002-35608

文献信息

• Synthesis of enantiomerically enriched (S)-(+)-2-aryl-4-pentenoic acids and (R)-(−)-2-aryl-4-pentenamides via microbial hydrolysis of nitriles, a chemoenzymatic approach to stereoisomers of α,γ-disubstituted γ-butyrolactones
  作者：Mei-Xiang Wang、Sheng-Min Zhao

  DOI：10.1016/s0957-4166(02)00470-6

  日期：2002.8

  In the presence of the nitrile hydratase amidase-containing Rhodococcus sp. AJ270 whole cell catalyst. 2-aryl-4-pentenenitriles 1 underwent enantioselective hydrolysis under mild conditions to afford (R)-(-)-2-aryl-4-pentenoic acid amides 2 and (S)-(+)-2-aryl-4-pentenoic acids 3 in almost quantitative yield. The amidase involved in the cells shows very high S-enantioselectivity whereas the nitrite hydratase exhibits low to moderate S-enatitioselectivity. The synthesis of stereoisomers of chi,gamma-disubstituted gamma-butyrolactones from iodolactonization of (S)-(+)-2-aryl-4-pentenoic acid was demonstrated. (C) 2002 Elsevier Science Ltd. All rights reserved.