(cis)-1-(p-Chlorophenyl)-2-phenylcyclopropane | 2001-61-8

• 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: (cis)-1-(p-Chlorophenyl)-2-phenylcyclopropane
• 英文别名: (cis)-1-chloro-4-(2-phenylcyclopropyl)benzene；cis-1-p-Chlorphenyl-2-phenylcyclopropan；rac-cis-1-(2-(4-chlorophenyl)cyclopropyl)benzene；1-chloro-4-[(1S,2R)-2-phenylcyclopropyl]benzene
• CAS: 2001-61-8
• 化学式: C₁₅H₁₃Cl
• 分子量: 228.721
• InChiKey: IMKVLZTWEQYKBR-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (cis)-1-(p-Chlorophenyl)-2-phenylcyclopropane 在 溴 作用下， 生成 1-p-(Chlorphenyl)-3-phenyl-1,3-dibrompropan
  参考文献：
  名称：

  Cyclopropane ring opening by photolytically generated bromine atoms

  摘要：

  DOI：

  10.1021/jo00909a001
• 作为产物：
  描述：

  4-氯查耳酮 在 氢氧化钾 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 反应 1.75h， 生成 (cis)-1-(p-Chlorophenyl)-2-phenylcyclopropane
  参考文献：
  名称：

  Kinetic study of the homolytic brominolysis of 1,2-diarylcyclopropanes

  摘要：

  DOI：

  10.1021/jo00325a014

文献信息

• Electron Transfer to Benzenes by Photoactivated Neutral Organic Electron Donor Molecules
  作者：Elise Cahard、Franziska Schoenebeck、Jean Garnier、Sylvain P. Y. Cutulic、Shengze Zhou、John A. Murphy

  DOI：10.1002/anie.201200084

  日期：2012.4.10

  Powerful reduction reactions: Simple organic electron donors, composed solely of the elements carbon, hydrogen, and nitrogen, reduce ground‐state benzene rings to their radical anions by electron transfer upon photoactivation (DMF=dimethylformamide).

  强大的还原反应：仅由碳，氢和氮元素组成的简单有机电子给体，通过光活化后的电子转移将基态苯环还原为自由基阴离子（DMF =二甲基甲酰胺）。
• 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。
• Cyclopropane–alkene metathesis by gold(<scp>i</scp>)-catalyzed decarbenation of persistent cyclopropanes
  作者：Mauro Mato、Inmaculada Martín-Torres、Bart Herlé、Antonio M. Echavarren

  DOI：10.1039/c9ob00359b

  日期：——

  A gold(I)-catalyzed cyclopropane–alkene metathesis has been demonstrated with two new families of cyclopropane derivatives of naphthalene and phenanthrene (benzo-fused norcaradienes). In this process, metal carbene units are transferred from a persistent cyclopropane to an alkene, upon release of naphthalene or phenanthrene, allowing the diastereoselective synthesis of a wide range of aryl and vinyl

  已经证明了金（I）催化的环丙烷-烯烃复分解反应具有两个新的萘和菲的环丙烷衍生物家族（苯并稠合的正二十碳烯）。在该方法中，在释放萘或菲时，金属卡宾单元从持久性环丙烷转移至烯烃，从而实现非对映选择性合成各种芳基和乙烯基环丙烷。
• Substituent Effects and the Mechanism of Gold to Alkene Benzylidene Transfer Employing a Gold Sulfonium Benzylide Complex
  作者：Mitch Rivers、Robert G. Carden、Ross A. Widenhoefer

  DOI：10.1021/acs.organomet.2c00097

  日期：2022.5.9

  sulfonium benzylide complex [(P)AuCHPh(SPh2)]+ B [3,5-CF3C6H3]4}− [P = P (t-Bu)2o-biphenyl; 1] at room temperature via the cationic two-coordinate gold benzylidene complex [(P)AuCHPh]+ (I) to form phenyclyclopropanes. The reactivity of p-substituted vinyl arenes toward I decreased with the decreasing electron donor ability of the vinyl arene (ρ = −1.49 ± 0.15), and the reactivity of aliphatic alkenes

  脂肪族和芳香族烯烃与金锍苄基络合物 [( P )AuCHPh(SPh 2 )] + B [3,5-CF 3 C 6 H 3 ] 4 } - [ P = P ( t -Bu ) 2邻联苯；1 ] 在室温下通过阳离子双配位金亚苄基配合物[( P )AuCHPh] + ( I ) 生成苯环丙烷。对位取代乙烯基芳烃对I的反应性随着乙烯基芳烃的电子供体能力降低（ρ = -1.49 ± 0.15），脂肪族烯烃对I的反应性在很大程度上取决于连接到更多取代烯烃末端的烷基数量。亚苄基向顺式和反式-β-甲基苯乙烯的转移发生，烯烃构型完全保留。亚苄基转移到乙烯基芳烃导致顺式的主要形成-环丙烷（dr = 4.1:1 至 13.9:1），而亚苄基转移至脂肪族烯烃的选择性通常较低（dr = 1.3:1 至 5.1:1）。我们所有的实验观察结果都与协调的、异步的、亲电的亚苄基转移机制一致。亚苄基转移的非对映选择性是在
• Olefin cyclopropanation with aryl diazocompounds upon catalysis by a dirhodium(II) complex
  作者：Mirella Verdecchia、Cristina Tubaro、Andrea Biffis

  DOI：10.1016/j.tetlet.2011.01.002

  日期：2011.3

  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.