Ethyl cis-5-hydroxybicyclo<3.3.0>octane-1-carboxylate | 129104-49-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl cis-5-hydroxybicyclo<3.3.0>octane-1-carboxylate
• 英文别名: ethyl (3aSR,6aSR)-6a-hydroxyhexahydropentalene-3a(1H)-carboxylate；ethyl cis-5-hydroxybicyclo<3.3.0>octanecarboxylate；Ethyl cis-5-hydroxybicyclo[3.3.0]octane-1-carboxylate
• CAS: 129104-49-0
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: SVVGZFDHWZNTTP-XYPYZODXSA-N

物化性质

• 沸点：
  274.7±23.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Ethyl cis-5-hydroxybicyclo<3.3.0>octane-1-carboxylate 在 lithium aluminium tetrahydride 、 lithium amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (3aSR,6aRS)-6a-(aminomethyl)hexahydropentalen-3a(1H)-ol
  参考文献：
  名称：

  Discovery of non-zwitterionic aryl sulfonamides as Nav1.7 inhibitors with efficacy in preclinical behavioral models and translational measures of nociceptive neuron activation

  摘要：

  Since zwitterionic benzenesulfonamide Na(v)1.7 inhibitors suffer from poor membrane permeability, we sought to eliminate this characteristic by replacing the basic moiety with non-basic bicyclic acetals and monocyclic ethers. These efforts led to the discovery of the non-zwitterionic aryl sulfonamide 49 as a selective Na(v)1.7 inhibitor with improved membrane permeability. Despite its moderate cellular activity, 49 exhibited robust efficacy in mouse models of neuropathic and inflammatory pain and modulated translational electromyogram measures associated with activation of nociceptive neurons. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.08.012
• 作为产物：
  描述：

  1-(3-溴丙基)-2-氧代环戊烷-1-羧酸乙酯 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 生成 Ethyl cis-5-hydroxybicyclo<3.3.0>octane-1-carboxylate
  参考文献：
  名称：

  Facile Ring Expansions of α-Halomethyl β-Keto Esters Mediated with SmI2

  摘要：

  用SmI2处理α-卤甲基β-酮酯，在HMPA或NiI2的帮助下得到了相应的一碳扩展产物。

  DOI：

  10.1055/s-2001-16064

文献信息

• Sequenced Reactions with Samarium(II) Iodide. Tandem Intramolecular Nucleophilic Acyl Substitution/Intramolecular Barbier Cyclizations
  作者：Gary A. Molander、Christina R. Harris

  DOI：10.1021/ja00118a007

  日期：1995.4

  Samarium(II) iodide has been employed to promote a tandem intramolecular nucleophilic acyl substitution/intramolecular Barbier cyclization sequence, generating bicyclic and tricyclic ring systems in excellent yield and high diastereoselectivity. Additionally, a highly versatile ring expansion-cyclization sequence allows entry into several different naturally occurring tricyclic ring systems containing seven- and eight-membered rings.
• Electroorganic chemistry. 124. Electroreductive intramolecular coupling of .alpha.-(.omega.-bromoalkyl) .beta.-keto esters
  作者：Tatsuya Shono、Naoki Kise、Nobuyuki Uematsu、Shinji Morimoto、Eiichi Okazaki

  DOI：10.1021/jo00304a014

  日期：1990.8