(1R,2S)-2-(benzyloxymethyl)-1-(4-bromophenyl)cyclopropanecarbonitrile

• 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: (1R,2S)-2-(benzyloxymethyl)-1-(4-bromophenyl)cyclopropanecarbonitrile
• 英文别名: (1R,2S)-1-(4-bromophenyl)-2-(phenylmethoxymethyl)cyclopropane-1-carbonitrile
• 化学式: C₁₈H₁₆BrNO
• 分子量: 342.235
• InChiKey: AUWIHJRNKLSRJL-AEFFLSMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对溴苯乙腈 、 苄氧基乙醛 、 三甲基碘化亚砜 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以61%的产率得到(1R,2S)-2-(benzyloxymethyl)-1-(4-bromophenyl)cyclopropanecarbonitrile
  参考文献：
  名称：

  Diastereoselective One-Pot Knoevenagel Condensation/Corey–Chaykovsky Cyclopropanation

  摘要：

  Efforts to substitute the cyclopropane ring in a series of aryl cyclopropylnitriles led to the discovery of an operationally simple one-pot method for Knoevenagel condensation and subsequent Corey-Chaykovsky cyclopropanation giving diastereomerically pure products as a racemic mixture of enantiomers. Method development and results for variably substituted aryl acetonitriles and aldehydes in the reaction are reported. A concise synthesis of (+/-)-bicifadine in two steps is provided to demonstrate the utility of the method.

  DOI：

  10.1021/jo302443k

文献信息

• Diastereoselective One-Pot Knoevenagel Condensation/Corey–Chaykovsky Cyclopropanation
  作者：Jeremy J. Clemens、Juliana L. Asgian、Brett B. Busch、Timothy Coon、Justin Ernst、Leonard Kaljevic、Paul J. Krenitsky、Timothy D. Neubert、Edwin J. Schweiger、Andreas Termin、Dean Stamos

  DOI：10.1021/jo302443k

  日期：2013.1.18

  Efforts to substitute the cyclopropane ring in a series of aryl cyclopropylnitriles led to the discovery of an operationally simple one-pot method for Knoevenagel condensation and subsequent Corey-Chaykovsky cyclopropanation giving diastereomerically pure products as a racemic mixture of enantiomers. Method development and results for variably substituted aryl acetonitriles and aldehydes in the reaction are reported. A concise synthesis of (+/-)-bicifadine in two steps is provided to demonstrate the utility of the method.