(trans)-1-(p-Cyanophenyl)-2-phenylcyclopropane | 35506-02-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (trans)-1-(p-Cyanophenyl)-2-phenylcyclopropane
• 英文别名: 4-(2-phenylcyclopropyl)benzonitrile；1-(p-Cyanophenyl)-2-phenylcyclopropan；4-[(1S,2S)-2-phenylcyclopropyl]benzonitrile
• CAS: 35506-02-6
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: PURWFOYEGZNJKY-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  甲醇 、 (trans)-1-(p-Cyanophenyl)-2-phenylcyclopropane 生成 1-(p-Cyanophenyl)-2-methoxy-3-phenylpropan
  参考文献：
  名称：

  Arylcyclopropane photochemistry. Photochemical addition of hydroxylic compounds to 1,2-diarylcyclopropanes

  摘要：

  DOI：

  10.1021/ja00822a026
• 作为产物：
  描述：

  benzaldehyde p-toluenesulfonylhydrazone 在 tetrakis-dirhodium(II)-N-perfluorooctylsulfonyl-L-prolinate 、 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 1-(p-Cyanophenyl)-2-phenylcyclopropan 、 (trans)-1-(p-Cyanophenyl)-2-phenylcyclopropane
  参考文献：
  名称：

  Olefin cyclopropanation with aryl diazocompounds upon catalysis by a dirhodium(II) complex

  摘要：

  A dirhodium(II) complex with N-perfluorooctylsulfonylprolinate ligands is found to catalyze the cyclopropanation of olefins with simple aryl diazomethanes. In contrast to previously reported dirhodium(II) catalysts, the present complex works well not only with very electron-rich olefins such as enol ethers, but also with styrenes. Consequently, the present catalyst allows to prepare functionalized diarylcyclopropanes in moderate yields with good diastereoselectivity for the cis product, whereas the enantioselectivity of the reaction appears negligible. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.002

文献信息

• Iron-catalyzed synthesis of cyclopropanes by <i>in situ</i> generation and decomposition of electronically diversified diazo compounds
  作者：Emmanuelle M. D. Allouche、Afnan Al-Saleh、André B. Charette

  DOI：10.1039/c8cc07060a

  日期：——

  The modular synthesis of a variety of trans 1,2-disubstituted cyclopropanes in a safe and user-friendly one-pot iron-catalyzed cyclopropanation reaction is described. Easily synthesized N-nosylhydrazones are used as diazo precursors, allowing the in situ generation of electron-rich diazo compounds under mild reaction conditions and their direct participation in the cyclopropanation reaction.

  描述了在安全和用户友好的一锅铁催化的环丙烷化反应中各种反式1,2-二取代的环丙烷的模块化合成。易于合成的N- nosylhydrazones用作重氮前体，可在温和的反应条件下原位生成富电子的重氮化合物，并直接参与环丙烷化反应。
• Kinetic study of the homolytic brominolysis of 1,2-diarylcyclopropanes
  作者：Douglas E. Applequist、Rick D. Gdanski

  DOI：10.1021/jo00325a014

  日期：1981.6