2-cyano-1-(hydroxymethyl)-2-phenylcyclopropane

• 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: 2-cyano-1-(hydroxymethyl)-2-phenylcyclopropane
• 英文别名: (1R,2R)-2-(hydroxymethyl)-1-phenylcyclopropane-1-carbonitrile
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: YDIYUDSRGPPHKA-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙腈 、 环氧溴丙烷 在 正丁基锂 、 lithium perchlorate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 2-cyano-1-(hydroxymethyl)-2-phenylcyclopropane 、 1alpha-Phenyl-2beta-(hydroxymethyl)cyclopropanecarbonitrile
  参考文献：
  名称：

  One-pot cyclization of dilithiated nitriles with isothiocyanates and epibromohydrin. Synthesis of 2-cyano-1-(hydroxymethyl)cyclopropanes and 2-cyanomethylidene-4-(hydroxymethyl)thiazolidines

  摘要：

  The cyclization of dilithiated nitriles with epibromohydrin afforded 2-cyano-1-(hydroxymethyl)cyclopropanes. 2-Cyanomethylidene-(4-hydroxymethyl)thiazolidines were prepared by one-pot cyclization of dilithiated nitriles with isothiocyanates and epibromohydrin. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.072

文献信息

• Chemo-, Regio-, and Diastereoselective Synthesis of Functionalized Cyclopropanes by Cyclization of Dilithiated Nitriles with Epibromohydrin
  作者：Peter Langer、Ilia Freifeld

  DOI：10.1021/ol010207c

  日期：2001.11.1

  [GRAPHICS]The cyclization of 1,1-dianions with epibromohydrin results in chemo-, regio-, and diastereoselective formation of functionalized hydroxymethyl cyclopropanes.
• Process for the Synthesis of (+)and (-)-1 Aryl-3-Azabicyclo(3.1.0) Hexanes
  申请人：Corley Edward G.

  公开号：US20100204486A1

  公开（公告）日：2010-08-12

  The present invention is concerned with novel processes for the preparation of (+)-1-aryl-3-azabicyclo[3,10]hexanes or a pharmaceutically acceptable salt thereof, and (−)-1-aryl-3-azabicyclo[3,10]hexanes or a pharmaceutically acceptable salt thereof. These compounds have pharmaceutical utility and are known to be useful for treating e.g., pain, depression, anxiety disorders, eating disorders and urinary incontinence.
• One-pot cyclization of dilithiated nitriles with isothiocyanates and epibromohydrin. Synthesis of 2-cyano-1-(hydroxymethyl)cyclopropanes and 2-cyanomethylidene-4-(hydroxymethyl)thiazolidines
  作者：Uwe Albrecht、Ilia Freifeld、Helmut Reinke、Peter Langer

  DOI：10.1016/j.tet.2006.03.072

  日期：2006.6

  The cyclization of dilithiated nitriles with epibromohydrin afforded 2-cyano-1-(hydroxymethyl)cyclopropanes. 2-Cyanomethylidene-(4-hydroxymethyl)thiazolidines were prepared by one-pot cyclization of dilithiated nitriles with isothiocyanates and epibromohydrin. (c) 2006 Elsevier Ltd. All rights reserved.