(S)-2-phenylpent-4-enenitrile | 947622-43-7

• 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-phenylpent-4-enenitrile
• 英文别名: 2-phenylpent-4-enenitrile；(2S)-2-phenylpent-4-enenitrile
• CAS: 947622-43-7
• 化学式: C₁₁H₁₁N
• 分子量: 157.215
• InChiKey: UPGWWAVLPCHBAC-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2-phenylpent-4-enenitrile 在 臭氧 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 9.0h， 以27%的产率得到(S)-3-cyano-3-phenylpropionaldehyde
  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：

  (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

文献信息

• Electrophotochemical Metal‐Catalyzed Enantioselective Decarboxylative Cyanation
  作者：Kai Yang、Yukang Wang、Sanzhong Luo、Niankai Fu

  DOI：10.1002/chem.202203962

  日期：——

  reaction conditions for radical decarboxylation to produce alkyl radicals, which could be effectively intercepted by asymmetric electrochemical Cu catalysis for the construction of C−CN bonds in a highly stereoselective manner.

  开发了一种可持续且高效的电光化学金属催化方案，用于将现成的脂肪族羧酸直接转化为手性烷基腈。电光化学 Ce 催化能够在温和的反应条件下自由基脱羧产生烷基自由基，其可以被不对称电化学 Cu 催化有效拦截，以高度立体选择性的方式构建 C-CN 键。
• Copper-Catalyzed Enantioselective Decarboxylative Cyanation of Benzylic Acids Promoted by Hypervalent Iodine(III) Reagents
  作者：Zhaoxia Li、Guang’an Zhang、Yue Song、Miaomiao Li、Zhongxian Li、Wei Ding、Junliang Wu

  DOI：10.1021/acs.orglett.3c00816

  日期：2023.5.5

  directly decarboxylative cyanation reactions of common alkyl carboxylic acids remain largely elusive. Herein, we report a protocol for copper-catalyzed direct and enantioselective decarboxylative cyanation of benzylic acids. The in situ activation of acid substrates by a commercially inexpensive hypervalent iodine(III) reagent promoted the yield of the alkyl radicals under mild reaction conditions without

  铜催化的不对称自由基氰化反应已成为快速构建 α-手性腈的有力策略。然而，普通烷基羧酸的直接脱羧氰化反应在很大程度上仍然难以捉摸。在此，我们报告了一种用于铜催化的苄酸直接和对映选择性脱羧氰化的方案。通过商业上廉价的高价碘 (III) 试剂原位激活酸性底物，在温和的反应条件下促进了烷基自由基的产率，而无需预官能化。结构多样的手性烷基腈以良好的收率和高对映选择性生产。此外，手性产物可以通过进一步的转化很容易地转化为其他有用的手性化合物。
• Heteroatom-Directed Alkylcyanation of Alkynes
  作者：Yoshiaki Nakao、Akira Yada、Tamejiro Hiyama

  DOI：10.1021/ja1017078

  日期：2010.7.28

  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.