(1R,2S,3R,5S)-2-benzyl-1,8,8-trimethyl-3-thiabicycl0<3.2.1>octane-3-oxide | 135608-55-8

• 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: (1R,2S,3R,5S)-2-benzyl-1,8,8-trimethyl-3-thiabicycl0<3.2.1>octane-3-oxide
• 英文别名: (1R,3S,4R,5S)-4-benzyl-1,8,8-trimethyl-3λ4-thiabicyclo[3.2.1]octane 3-oxide
• CAS: 135608-55-8
• 化学式: C₁₇H₂₄OS
• 分子量: 276.443
• InChiKey: CANXFLAAJPELRZ-RRIFGTCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  (1R,2S,3R,5S)-2-benzyl-1,8,8-trimethyl-3-thiabicycl0<3.2.1>octane-3-oxide 在 乙酰氯 、 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (1R,4R,5S)-4-Benzyl-1,8,8-trimethyl-3-thia-bicyclo[3.2.1]octane
  参考文献：
  名称：

  Preparation of optically active epoxides via sulfur ylides. Origin of the chiral induction.

  摘要：

  The sulfonium ylide derived from (1R, 2S, 3R, 5S)-2,3-dibenzyl-1,8,8-trimethyl-3-thianiumbicyclo-[3.2.1]octan perchlorate 6 (prepared from (1R,3S)-(+)-camphoric acid) transfers its benzylidene group to some carbonyl compounds with ee's approaching enatiomeric purity. It is suggested that in this system the chiral induction is due to the facial selectivity at the ylide rather than the carbonyl carbon.

  DOI：

  10.1016/s0957-4166(00)82121-7
• 作为产物：
  描述：

  (1R,5S)-1,8,8-Trimethyl-3-thia-bicyclo[3.2.1]octane 在 magnesium bis(monoperoxyphthalate)hexahydrate 、 甲基锂 作用下， 以 乙醇 、 水 为溶剂， 反应 9.25h， 生成 (1R,2S,3R,5S)-2-benzyl-1,8,8-trimethyl-3-thiabicycl0<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