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,2S)-2-(hydroxymethyl)-1-(p-tolyl)cyclopropanecarbonitrile；(1R,2S)-2-(hydroxymethyl)-1-(4-methylphenyl)cyclopropane-1-carbonitrile
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: CIBGDKPOBCTCCK-NEPJUHHUSA-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

• Methods and compositions for production, formulation and use of 1-aryl-3-azabicyclo[3.1.0]hexanes
  申请人：Skolnick Phil

  公开号：US20060223875A1

  公开（公告）日：2006-10-05

  The invention provides novel 1-aryl-3-azabicyclo[3.1.0]hexanes that are active for modulating biogenic amine transport, along with compositions and methods for using these compounds to treat central nervous system disorders. Certain 1-aryl-3-azabicyclo[3.1.0]hexanes are provided that have at least one substituent on the aryl ring. In other embodiments 1-aryl-3-azabicyclo[3.1.0]hexanes are provided that have a substitution on the nitrogen at the ‘3’ position. In additional embodiments 1-aryl-3-azabicyclo[3.1.0]hexanes are provided which have one substitution on the aryl ring, as well as a substitution on the nitrogen at the ‘3’ position. The invention also provides novel methods of making aryl- and aza-substituted 1-aryl-3-azabicyclo[3.1.0]hexanes, including synthetic methods that form novel intermediate compounds of the invention for producing aryl- and aza-substituted 1-aryl-3-azabicyclo[3.1.0]hexanes.

  本发明提供了新型的1-芳基-3-氮杂双环[3.1.0]己烷，它们对生物胺转运的调节具有活性，以及使用这些化合物治疗中枢神经系统疾病的组合物和方法。提供了某些1-芳基-3-氮杂双环[3.1.0]己烷，其在芳基环上至少有一个取代基。在其他实施例中，提供了在“3”位的氮上有取代基的1-芳基-3-氮杂双环[3.1.0]己烷。在其他实施例中，提供了在芳基环上有一个取代基以及在“3”位的氮上有一个取代基的1-芳基-3-氮杂双环[3.1.0]己烷。本发明还提供了制备芳基和氮取代的1-芳基-3-氮杂双环[3.1.0]己烷的新方法，包括形成本发明的新中间化合物的合成方法，用于生产芳基和氮取代的1-芳基-3-氮杂双环[3.1.0]己烷。
• Methods and compositions for the treatment of neuropathies and related disorders
  申请人：Lippa S. Arnold

  公开号：US20070082939A1

  公开（公告）日：2007-04-12

  The present invention provides novel compositions and methods for treating symptoms associated with neuropathic disorders such as hyperalgesia, allodynia, and parasthesias, using a 1-aryl-3-azabicyclo[3.1.0] hexane. The invention further relates to the use of 1-aryl-3-azabicyclo[3.1.0] hexanes in pharmaceutical compositions and methods for treating neuropathic disorders and related symptoms in mammals. Patients amenable to treatment according to the invention include those suffering from diabetic neuropathies, post-herpetic neuralgia, trigeminal neuralgia, chronic lower back pain, sciatica, idiopathic and post-traumatic neuropathies, HIV-associated neuropathic pain, among many other neuropathic disorders and related symptoms.

  本发明提供了一种新型组合物和方法，用于治疗与神经病理性疾病相关的症状，如过度疼痛、触痛和感觉异常，使用1-芳基-3-氮杂双环[3.1.0]己烷。本发明还涉及在制药组合物中使用1-芳基-3-氮杂双环[3.1.0]己烷以及治疗哺乳动物神经病理性疾病和相关症状的方法。根据本发明可治疗的患者包括患有糖尿病神经病变、带状疱疹后遗神经痛、三叉神经痛、慢性腰痛、坐骨神经痛、特发性和创伤后神经病变、HIV相关神经病理性疼痛等许多神经病理性疾病和相关症状的患者。
• 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：Merck Sharp & Dohme Corp.

  公开号：EP2016053B1

  公开（公告）日：2010-11-10