cis-di-O-methanesulfonyl-1,3-bis(hydroxymethyl)cyclopentane | 157329-99-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: cis-di-O-methanesulfonyl-1,3-bis(hydroxymethyl)cyclopentane
• 英文别名: [(1S,3R)-3-(methylsulfonyloxymethyl)cyclopentyl]methyl methanesulfonate
• CAS: 157329-99-2
• 化学式: C₉H₁₈O₆S₂
• 分子量: 286.37
• InChiKey: DBJGFRASTHBFMK-DTORHVGOSA-N

物化性质

• 沸点：
  486.1±18.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  cis-di-O-methanesulfonyl-1,3-bis(hydroxymethyl)cyclopentane 在 sodium sulfide 、 sodium hydroxide 、 magnesium(II) perchlorate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 107.5h， 生成 endo-(1SR,5RS)-3-thiabicyclo<3.2.1>octane-3-oxide
  参考文献：
  名称：

  Unusual stereochemical results in the reaction of alpha-lithio derivatives of bicyclic sulfoxides

  摘要：

  The stereochemistry of the reaction of the lithio derivatives of two sets of isomeric 3-thia[3.2.1]octane-3-oxides with electrophiles such as benzyl bromide, acetone and D2O has been studied. Introduction of deuterium always occurred cis to the S=O bond as expected on the basis of earlier results described by Marquet for the related thiane-S-oxides. In contrast, benzyl groups were introduced either cis or trans to the existing S=O bond. The results are most readily rationalized in terms of a planar configuration at the a-carbanion center. The unexpected cis benzylations are due to steric hindrance of the preferred approach anti to the S=O bond by either the ethano bridge or the 8-endo methyl group.

  DOI：

  10.1016/s0040-4020(01)90458-2
• 作为产物：
  描述：

  (1S,3R)-环戊烷-1,3-二甲酸 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 cis-di-O-methanesulfonyl-1,3-bis(hydroxymethyl)cyclopentane
  参考文献：
  名称：

  Aryl sulfones: a new class of γ-secretase inhibitors

  摘要：

  The development of a novel series of 4-aryl, 4-phenylsulfonyl cyclohexananone-derived gamma-secretase inhibitors for the potential treatment of Alzheimer's disease is described. (c) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.017