(1R,5S)-1-(3-chlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one | 910028-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,5S)-1-(3-chlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one
• 英文别名: (-)-1-(3-chlorophenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one；(+/-)-1-(3-chlorophenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one
• CAS: 910028-52-3
• 化学式: C₁₁H₉ClO₂
• 分子量: 208.644
• InChiKey: MVTGZCCSDXOZTH-KCJUWKMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,5S)-1-(3-chlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one 在 三氯化铝 、 sodium azide 、 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (1R,2S)-2-(azidomethyl)-1-(3-chlorophenyl)-N,N-diethylcyclopropanecarboxamide
  参考文献：
  名称：

  Synthesis of enantiomerically pure milnacipran analogs and inhibition of dopamine, serotonin, and norepinephrine transporters

  摘要：

  A series of Milnacipran analogs with variation in the aromatic moiety were prepared in high enantionteric excess. Structure-activity relationships for two parallel enantionteric series are described. The (-)-(1R,2S)-naphthyl analog (8h) showed the highest potency in the two series and is a triple reuptake inhibitor of the SERT, NET, and DAT. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.054
• 作为产物：
  描述：

  allyl 2-(3-chlorophenyl)-2-diazoacetate 在 辛酸铑 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1R,5S)-1-(3-chlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Identification of a new series of non-peptidic NK3 receptor antagonists

  摘要：

  The identification and structure-activity relationships of 2-aminomethyl-1-aryl cyclopropane carboxamides as novel NK3 receptor antagonists are reported. The compound series was optimized to give analogues with low nanomolar binding to the NK3 receptor and brain exposure, leading to activity in vivo in the senktide-induced hypoactivity model in gerbils. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.135

文献信息

• Stereocontrolled Synthesis of Trisubstituted Cyclopropanes:  Expedient, Atom-Economical, Asymmetric Syntheses of (+)-Bicifadine and DOV21947
  作者：Feng Xu、Jerry A. Murry、Bryon Simmons、Edward Corley、Kenneth Fitch、Sandor Karady、David Tschaen

  DOI：10.1021/ol061650w

  日期：2006.8.1

  An expedient, atom-economical, asymmetric synthesis of 1-aryl-3-azabicyclo[3.1.0]hexanes, including (+)-Bicifadine and DOV21947, in a single-stage through process without isolation of any intermediates has been developed. The key of this synthesis is the in-depth mechanistic understanding of the complicated epoxy nitrile coupling at each reaction stage. Therefore, the desired trisubstituted cyclopropane can be prepared in high ee and yield by controlling the reaction pathway through manipulating the nitrile anion aggregation state.