(+/-)-1-(thiophen-2-yl)-3-oxa-bicyclo[3.1.0]hexan-2-one | 942493-40-5

• 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: (+/-)-1-(thiophen-2-yl)-3-oxa-bicyclo[3.1.0]hexan-2-one
• 英文别名: (-)-1-(thiophen-2-yl)-3-oxa-bicyclo[3.1.0]hexan-2-one
• CAS: 942493-40-5
• 化学式: C₉H₈O₂S
• 分子量: 180.227
• InChiKey: HWMYYILGECIWGS-HZGVNTEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(thiophen-2-yl)-3-oxa-bicyclo[3.1.0]hexan-2-one 在 palladium on activated charcoal 三氯化铝 、 sodium azide 、 四溴化碳 、 氢气 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (1R,2R)-2-(aminomethyl)-N,N-diethyl-1-(thiophen-2-yl)cyclopropanecarboxamide
  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：

  在 rhodium(II) acetate dimer 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (+/-)-1-(thiophen-2-yl)-3-oxa-bicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Studies on the structure–activity relationship of bicifadine analogs as monoamine transporter inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.05.077

文献信息

• 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.