diethyl cis-2-benzoyl-3-(4-chlorophenyl)cyclopropane-1,1-dicarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl cis-2-benzoyl-3-(4-chlorophenyl)cyclopropane-1,1-dicarboxylate
• 英文别名: diethyl (2R,3R)-2-benzoyl-3-(4-chlorophenyl)cyclopropane-1,1-dicarboxylate
• 化学式: C₂₂H₂₁ClO₅
• 分子量: 400.859
• InChiKey: RXFDQWDTSGAUMG-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl cis-2-benzoyl-3-(4-chlorophenyl)cyclopropane-1,1-dicarboxylate 、 4-氯异硫氰酸苯酯 在 aluminum (III) chloride 作用下， 以 硝基甲烷 为溶剂， 反应 0.08h， 以57%的产率得到(4,5-trans, 2Z)-diethyl 4-benzoyl-5-(4-chlorophenyl)-2-(4-chlorophenylimino)dihydrothiophene-3,3(2H)-dicarboxylate
  参考文献：
  名称：

  AlCl3-promoted [3 + 2] annulation of cis-2,3-disubstituted cyclopropane 1,1-diesters with isothiocyanates: stereoselective synthesis of densely substituted 2-iminodihydrothiophenes

  摘要：

  人们发现顺式-2,3-二取代环丙烷1,1-二酯在AlCl3促进的与异硫氰酸酯的[3 + 2]-成环反应中比其相应的反式异构体更具反应性。与顺式环丙烷的反应在几分钟内完成，以中等至优异的产率提供各种密集取代的非对映体纯2-亚氨基二氢噻吩。

  DOI：

  10.1039/c3ob41678j
• 作为产物：
  描述：

  2-溴-3-(4-氯苯基)-1-苯基丙-2-烯-1-酮 、 丙二酸二乙酯 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以46%的产率得到diethyl trans-2-benzoyl-3-(4-chlorophenyl)-cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Stereoselective cyclopropanation of α-bromochalcone with diethyl malonate promoted by K2CO3

  摘要：

  A new Michael-initiated cyclopropanation reaction using alpha-bromochalcones as Michael acceptor was developed. Compared to previous works using arylidenemalonates as Michael acceptor, this novel protocol could improve the synthesis of trans-isomers of diethyl 2-benzoyl-3-phenyl-cyclopropane-1,1-dicarboxylates. More importantly, this method also provided the first access to the cis-isomers of these densely substituted cyclopropanes with the Michael-initiated ring closure (MIRC) strategy, albeit with a poor diastereoselectivity. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.02.011

文献信息

• AlCl₃-Catalyzed [3+2] Annulations of<i>cis</i>-2,3-Disubstituted Cyclopropane 1,1-Diesters with Cyclic Ketones: Diastereoselective Construction of Spirotetrahydrofurans
  作者：Gaosheng Yang、Tingting Wang、Jun Chai、Zhuo Chai

  DOI：10.1002/ejoc.201403325

  日期：2015.2

  The stereoselective [3+2] annulations of cis-2,3-disubstituted cyclopropane 1,1-diesters with cyclic/acyclic aliphatic ketones were effected by AlCl3 to provide highly functionalized spirotetrahydrofurans in moderate to excellent yields under very mild conditions.

  顺式-2,3-二取代环丙烷1,1-二酯与环状/非环状脂肪族酮的立体选择性[3+2]环化受AlCl3影响，在非常温和的条件下以中等至优异的产率提供高度官能化的螺四氢呋喃。
• <i>cis</i>-2,3-Disubstituted Cyclopropane 1,1-Diesters in [3 + 2] Annulations with Aldehydes: Highly Diastereoselective Construction of Densely Substituted Tetrahydrofurans
  作者：Gaosheng Yang、Yongxian Sun、Yue Shen、Zhuo Chai、Shuangliu Zhou、Jiang Chu、Jun Chai

  DOI：10.1021/jo400554a

  日期：2013.6.7

  A series of cis-2,3-disubstituted cyclopropane 1,1-diesters were examined in the AlCl3-promoted [3 + 2]-annulations with aldehydes. In this reaction, these cis-cyclopropanes displayed reactivities starkly different from their trans counterparts in terms of the high chemical yields (up to 98%) and provided the desired annulation products with excellent diastereomeric purity. This protocol provides a

  在AlCl 3促进的[3 + 2]醛环中，研究了一系列顺式-2,3-二取代的环丙烷1,1-二酯。在该反应中，这些顺式-环丙烷在高化学收率（高达98％）方面显示出与反式对应物完全不同的反应性，并提供具有优异的非对映体纯度的所需环合产物。该方案提供了一种简便且高度立体选择性的方法来构建合成有用的五取代的四氢呋喃，而该五取代的四氢呋喃难以使用其他方法获得。
• AlCl3-promoted [3 + 2] annulation of cis-2,3-disubstituted cyclopropane 1,1-diesters with isothiocyanates: stereoselective synthesis of densely substituted 2-iminodihydrothiophenes
  作者：Yongxian Sun、Gaosheng Yang、Zhuo Chai、Xiaolong Mu、Jun Chai

  DOI：10.1039/c3ob41678j

  日期：——

  cis-2,3-Disubstituted cyclopropane 1,1-diesters were found to be much more reactive than their corresponding trans-isomers in the AlCl3-promoted [3 + 2]-annulations with isothiocyanates. The reaction with the cis-cyclopropanes proceeded to completion within minutes, providing a variety of densely substituted diastereomerically pure 2-iminodihydrothiophenes in moderate to excellent yields.

  人们发现顺式-2,3-二取代环丙烷1,1-二酯在AlCl3促进的与异硫氰酸酯的[3 + 2]-成环反应中比其相应的反式异构体更具反应性。与顺式环丙烷的反应在几分钟内完成，以中等至优异的产率提供各种密集取代的非对映体纯2-亚氨基二氢噻吩。
• Stereoselective cyclopropanation of α-bromochalcone with diethyl malonate promoted by K2CO3
  作者：Yongxian Sun、Gaosheng Yang、Yue Shen、Zan Hua、Zhuo Chai

  DOI：10.1016/j.tet.2013.02.011

  日期：2013.4

  A new Michael-initiated cyclopropanation reaction using alpha-bromochalcones as Michael acceptor was developed. Compared to previous works using arylidenemalonates as Michael acceptor, this novel protocol could improve the synthesis of trans-isomers of diethyl 2-benzoyl-3-phenyl-cyclopropane-1,1-dicarboxylates. More importantly, this method also provided the first access to the cis-isomers of these densely substituted cyclopropanes with the Michael-initiated ring closure (MIRC) strategy, albeit with a poor diastereoselectivity. (C) 2013 Published by Elsevier Ltd.