(1R,5S)-1-(3,4-dichlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one | 910028-58-9

• 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,5S)-1-(3,4-dichlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one
• 英文别名: (+)-1-(3,4-dichlorophenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one
• CAS: 910028-58-9
• 化学式: C₁₁H₈Cl₂O₂
• 分子量: 243.089
• InChiKey: RMGUFGMJSKNPDK-HQJQHLMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 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
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,5S)-1-(3,4-dichlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one 在 aluminum (III) chloride 、 硫酸 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (-)-1-(3,4-dichlorophenyl)-3-oxa-bicyclo[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
• 作为产物：
  描述：

  (1R,2S)-1-(3,4-dichlorophenyl)-2-(hydroxymethyl)cyclopropane-1-carbonitrile 在 sodium hydroxide 、 乙醇 、 水 、 盐酸 作用下， 反应 18.0h， 以55%的产率得到(1R,5S)-1-(3,4-dichlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  WO2008/57575

  摘要：

  公开号：

文献信息

• Novel Arylbicyclo[3.1.0]Hexylamines And Methods And Compositions For Their Preparation And Use
  申请人：Skolnick Phil

  公开号：US20080194696A1

  公开（公告）日：2008-08-14

  The invention provides novel arylbicyclo[3.1.0]hexylamines, and related processes and intermediates for preparing these compounds, as well as compositions and methods employing these compounds for the treatment and/or prevention of central nervous system (CNS) disorders, including but not limited to depression and anxiety.

  本发明提供了新型芳基双环[3.1.0]己基胺，以及制备这些化合物的相关过程和中间体，以及使用这些化合物的组合物和方法，用于治疗和/或预防中枢神经系统（CNS）疾病，包括但不限于抑郁症和焦虑症。
• Arylbicyclo[3.1.0]hexylamines and methods and compositions for their preparation and use
  申请人：DOV Pharmaceutical, Inc.

  公开号：US08138377B2

  公开（公告）日：2012-03-20

  The invention provides novel arylbicyclo[3.1.0]hexylamines, and related processes and intermediates for preparing these compounds, as well as compositions and methods employing these compounds for the treatment and/or prevention of central nervous system (CNS) disorders, including but not limited to depression and anxiety.

  本发明提供了新型芳基双环[3.1.0]己基胺，以及用于制备这些化合物的相关过程和中间体，以及使用这些化合物治疗和/或预防中枢神经系统（CNS）疾病的组合物和方法，包括但不限于抑郁症和焦虑症。
• 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.
• Synthesis of enantiomerically pure milnacipran analogs and inhibition of dopamine, serotonin, and norepinephrine transporters
  作者：Heidi Roggen、Jan Kehler、Tine Bryan Stensbøl、Tore Hansen

  DOI：10.1016/j.bmcl.2007.02.054

  日期：2007.5

  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.
• Studies on the structure–activity relationship of bicifadine analogs as monoamine transporter inhibitors
  作者：Mingzhu Zhang、Florence Jovic、Troy Vickers、Brian Dyck、Junko Tamiya、Jonathan Grey、Joe A. Tran、Beth A. Fleck、Rebecca Pick、Alan C. Foster、Chen Chen

  DOI：10.1016/j.bmcl.2008.05.077

  日期：2008.7

  Compounds with various activities and selectivities were discovered through structure -activity relationship studies of bicifadine analogs as monoamine transporter inhibitors. The norepinephrine-selective 2-thienyl compound S-6j was efficacious in a rodent pain model. (C) 2008 Elsevier Ltd. All rights reserved.