(1R,3R,5S)-1,8,8-trimethyl-3-thiabicyclo<3.2.1>octane-3-oxide | 157239-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻庚烷
• 英文名称: (1R,3R,5S)-1,8,8-trimethyl-3-thiabicyclo<3.2.1>octane-3-oxide
• 英文别名: (1R,3S,5S)-1,8,8-trimethyl-3λ4-thiabicyclo[3.2.1]octane 3-oxide
• CAS: 157239-04-8
• 化学式: C₁₀H₁₈OS
• 分子量: 186.318
• InChiKey: CMFNSTZBOPMMSS-QRTLGDNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  丙酮 、 (1R,3R,5S)-1,8,8-trimethyl-3-thiabicyclo<3.2.1>octane-3-oxide 在 甲基锂 作用下， 生成 (1R,3R,4S,5S)-4-(1-methyl-ethan-1-ol)-1,8,8-trimethyl-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：

  在 sodium hydroxide 作用下， 反应 48.0h， 生成 (1R,3R,5S)-1,8,8-trimethyl-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

文献信息

• Unusual stereochemical results in the reaction of alpha-lithio derivatives of bicyclic sulfoxides
  作者：Robert N. Ben、Livain Breau、C. Bensimon、T. Durst

  DOI：10.1016/s0040-4020(01)90458-2

  日期：1994.1

  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.