(+)-1-(thiophen-3-yl)-3-oxa-bicyclo[3.1.0]hexan-2-one | 942493-80-3

• 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: (+)-1-(thiophen-3-yl)-3-oxa-bicyclo[3.1.0]hexan-2-one
• CAS: 942493-80-3
• 化学式: C₉H₈O₂S
• 分子量: 180.227
• InChiKey: HAJIAZHVZHUNCP-IONNQARKSA-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-3-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 (1S,2R)-2-(aminomethyl)-N,N-diethyl-1-(thiophen-3-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：

  3-噻吩乙腈 、 左旋环氧氯丙烷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (+)-1-(thiophen-3-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

• Studies on a series of milnacipran analogs containing a heteroaromatic group as potent norepinephrine and serotonin transporter inhibitors
  作者：Troy Vickers、Brian Dyck、Junko Tamiya、Mingzhu Zhang、Florence Jovic、Jonathan Grey、Beth A. Fleck、Anna Aparicio、Michael Johns、Liping Jin、Hui Tang、Alan C. Foster、Chen Chen

  DOI：10.1016/j.bmcl.2008.04.045

  日期：2008.6

  A series of milnacipran analogs containing a heteroaromatic group were synthesized and studied as monoamine transporter inhibitors. Many compounds exhibited higher potency than milnacipran at NET and NET/SERT with no significant change in lipophilicity. For example, compound R-26f was about 10-fold more potent than milnacipran with IC(50) values of 8.7 and 26 nM at NET and SERT, respectively. (C) 2008 Elsevier Ltd. All rights reserved.
• WO2007/98356
  申请人：——

  公开号：——

  公开（公告）日：——