(E)-3-(4-bromophenyl)-2-(4-methoxybenzoyl)prop-2-enenitrile | 1261378-71-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(4-bromophenyl)-2-(4-methoxybenzoyl)prop-2-enenitrile
• CAS: 1261378-71-5
• 化学式: C₁₇H₁₂BrNO₂
• 分子量: 342.192
• InChiKey: OEJJAMBMGWNTHJ-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-bromophenyl)-2-(4-methoxybenzoyl)prop-2-enenitrile 在 叔丁基过氧化氢 、 S-Α,Α-双(3,5-二甲基苯基)脯氨醇 作用下， 以 癸烷 、 间二甲苯 为溶剂， 以99%的产率得到(2R,3S)-3-(4-bromophenyl)-2-(4-methoxybenzoyl)oxirane-2-carbonitrile
  参考文献：
  名称：

  Organocatalytic Stereoselective Epoxidation of Trisubstituted Acrylonitriles

  摘要：

  The first diastereospecific and enantioselective epoxidation of trans-2-aroyl-3-arylacrylonitriles by means of the commercially available diaryl L-prolinol/tert-butyl hydroperoxide system has been developed. These diversely functionalized epoxides were obtained in excellent yield (up to 99%), complete diastereoselectivity for the transisomer, and good enantioselectivity (up to 84% ee). Highly enantioenriched epoxides can be easily obtained after a single crystallization (ee > 90%).

  DOI：

  10.1021/jo102020a
• 作为产物：
  描述：

  对溴苯甲醛 、 4-甲氧基苯甲酰基乙腈 在 三乙烯二胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 (E)-3-(4-bromophenyl)-2-(4-methoxybenzoyl)prop-2-enenitrile
  参考文献：
  名称：

  One-pot highly diastereoselective annulation to N-unprotected tetrasubstituted 2-pyrrolines

  摘要：

  已开发出一种有效的一锅顺序Michael加成/去保护/环化/互变异构化方法，用于合成未保护的全取代的trans-2-吡咯烯。

  DOI：

  10.1039/c4gc02191f

文献信息

• Enantioselective synthesis of substituted pyrans via amine-catalyzed Michael addition and subsequent enolization/cyclisation
  作者：Utpal Das、Chan-Hui Huang、Wenwei Lin

  DOI：10.1039/c2cc31445b

  日期：——

  An organocatalytic construction of optically enriched substituted pyran derivatives via amine-catalyzed Michael addition and subsequent enolization/cyclisation has been described starting from electronically poor alkenes. Functionalized pyrans were obtained in high enantioselectivities (up to 96%) and good yields (up to 90%) having three contiguous chiral centers.

  从电子性差的烯类开始，通过胺催化的迈克尔加成和随后的烯醇化/环化，有机催化地构建了光学富集的取代吡喃衍生物。得到的官能化吡喃具有较高的对映选择性（高达 96%）和良好的产率（高达 90%），并具有三个连续的手性中心。
• Phosphine-catalysed intermolecular cyclopropanation reaction between benzyl bromides and activated alkenes
  作者：Jie Zhang、Xue Song、Zhi-Chao Chen、Wei Du、Ying-Chun Chen

  DOI：10.1039/d2nj03417d

  日期：——

  While phosphine-mediated reactions have been extensively explored over the past few decades, the catalytic cyclopropanation reaction via a phosphonium ylide pathway has been significantly underdeveloped, and an intermolecular version still remains to be disclosed. Presented herein is a catalytic cyclopropanation reaction between readily available benzyl bromides and activated alkenes, such as α-cyano

  尽管在过去的几十年中，膦介导的反应得到了广泛的探索，但通过鏻叶立德途径的催化环丙烷化反应还没有得到充分的开发，分子间的反应仍有待公开。本文介绍的是容易获得的苄基溴和活化烯烃（例如 α-氰基查耳酮）之间的催化环丙烷化反应，通过原位形成鏻叶立德中间体。高效地构建了一系列密集官能化的环丙烷衍生物，具有优异的非对映选择性，经过简单的转化，可以进一步转化为五元杂环化合物。此外，通过使用市售的 DuPhos 催化剂可以获得中等的对映选择性。
• One-pot highly diastereoselective annulation to N-unprotected tetrasubstituted 2-pyrrolines
  作者：Sara Meninno、Amedeo Capobianco、Andrea Peluso、Alessandra Lattanzi

  DOI：10.1039/c4gc02191f

  日期：——

  An effective one-pot sequential Michael addition/deprotection/cyclization/tautomerization approach to N-unprotected fully substituted trans-2-pyrrolines has been developed.

  已开发出一种有效的一锅顺序Michael加成/去保护/环化/互变异构化方法，用于合成未保护的全取代的trans-2-吡咯烯。
• Organocatalytic Stereoselective Epoxidation of Trisubstituted Acrylonitriles
  作者：Claudia De Fusco、Consiglia Tedesco、Alessandra Lattanzi

  DOI：10.1021/jo102020a

  日期：2011.1.21

  The first diastereospecific and enantioselective epoxidation of trans-2-aroyl-3-arylacrylonitriles by means of the commercially available diaryl L-prolinol/tert-butyl hydroperoxide system has been developed. These diversely functionalized epoxides were obtained in excellent yield (up to 99%), complete diastereoselectivity for the transisomer, and good enantioselectivity (up to 84% ee). Highly enantioenriched epoxides can be easily obtained after a single crystallization (ee > 90%).