(1S,5R)-1-(4-chlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one | 247102-85-8

• 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: (1S,5R)-1-(4-chlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one
• 英文别名: (-)-1-(4-chlorophenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one；(1S,5R)-1-(4-chlorophenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one
• CAS: 247102-85-8
• 化学式: C₁₁H₉ClO₂
• 分子量: 208.644
• InChiKey: HEMWVVNJMILOET-GZMMTYOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 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：

  (1S,5R)-1-(4-chlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one 在 氨 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 (1S,2R)-1-(4-chlorophenyl)-2-hydroxymethylcyclopropane carboxamide
  参考文献：
  名称：

  Synthesis of Conformationally Restricted Analogs of Baclofen, a Potent GABAB Receptor Agonist, by the Introduction of a Cyclopropane Ring.

  摘要：

  设计了一些构象受限的baclofen (2) 类似物，即5、6及其对映体ent-5和ent-6，通过引入环丙烷环来限制其构象，作为潜在的GABAB受体配体。在苯/四氢呋喃的存在下，(R)-环氯醇[(R)-7]与(4-氯苯基)乙腈在NaNH₂的作用下反应，得到手性环丙烷衍生物11和12，随后分别将其转化为目标化合物5和6。它们对应的对映体ent-5和ent-6也以(S)-环氯醇[(S)-7]为起始物合成。

  DOI：

  10.1248/cpb.47.1188
• 作为产物：
  描述：

  左旋环氧氯丙烷 、 对氯苯乙腈 在 sodium amide 、 氢氧化钾 作用下， 以 苯 、 乙醇 为溶剂， 反应 5.0h， 生成 (1S,5R)-1-(4-chlorophenyl)-3-oxabicyclo[3.1.0]hexan-2-one
  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

文献信息

• Cyclopropyl derivatives as nk3 receptor antagonists
  申请人：Kehler Jan

  公开号：US20060281746A1

  公开（公告）日：2006-12-14

  The present invention relates to cyclopropyl derivatives of formula (I) and salt thereof. These compounds are NK3 receptor antagonists and may therefore be useful for treatment of diseases where the NK3 receptor is implicated, e.g. psychotic disorders.

  本发明涉及式（I）的环丙基衍生物及其盐。这些化合物是NK3受体拮抗剂，因此可能对涉及NK3受体的疾病如精神疾患的治疗有用。
• 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.
• CYCLOPROPYL DERIVATIVES AS NK3 RECEPTOR ANTAGONISTS
  申请人：H. Lundbeck A/S

  公开号：EP1656349B1

  公开（公告）日：2011-10-12
• US7834008B2
  申请人：——

  公开号：US7834008B2

  公开（公告）日：2010-11-16
• 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.