2-cyano-1-(hydroxymethyl)-2-(p-tolyl)cyclopropane

• 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-(p-tolyl)cyclopropane
• 英文别名: (1R,2R)-2-(hydroxymethyl)-1-(4-methylphenyl)cyclopropane-1-carbonitrile
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: CIBGDKPOBCTCCK-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  对甲基苯乙腈 、 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， 生成 2-cyano-1-(hydroxymethyl)-2-(p-tolyl)cyclopropane 、 2-cyano-1-(hydroxymethyl)-2-(p-tolyl)cyclopropane
  参考文献：
  名称：

  Chemo-, Regio-, and Diastereoselective Synthesis of Functionalized Cyclopropanes by Cyclization of Dilithiated Nitriles with Epibromohydrin

  摘要：

  [GRAPHICS]The cyclization of 1,1-dianions with epibromohydrin results in chemo-, regio-, and diastereoselective formation of functionalized hydroxymethyl cyclopropanes.

  DOI：

  10.1021/ol010207c

文献信息

• WO2006/96810
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• 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.
• [EN] PROCESS FOR THE SYNTHESIS OF (+) AND (-)-1-ARYL-3-AZABICYCLO[3.1.0]HEXANES<br/>[FR] SYNTHÈSE DE (+) ET (-)-1-ARYL-3-AZABICYCLO[3.1.0]HEXANES
  申请人：MERCK & CO INC

  公开号：WO2007127421A2

  公开（公告）日：2007-11-08

  [EN] 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.
  [FR] La présente invention concerne de nouvelles méthodes de préparation de (+)-1-aryl-3-azabicyclo[3,10]hexanes ou d'un sel de qualité pharmaceutique de ces composés, et de (-)-1-aryl-3-azabicyclo[3,10]hexanes ou d'un sel de qualité pharmaceutique de ces composés. Lesdits composés sont connus pour leur utilité pharmaceutique dans le traitement de la douleur, de la dépression, des troubles de l'anxiété, des troubles de l'alimentation et de l'incontinence urinaire, notamment.