(R)-cis-2-bromophenyl 4-(tert-butyl)cyclohexyl sulfoxide | 249743-98-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-cis-2-bromophenyl 4-(tert-butyl)cyclohexyl sulfoxide
• CAS: 249743-98-4
• 化学式: C₁₆H₂₃BrOS
• 分子量: 343.328
• InChiKey: JWZOXUMMWUIIFG-QHRIQVFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (R)-cis-2-bromophenyl 4-(tert-butyl)cyclohexyl sulfoxide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 生成 (R)-4-(tert-butyl)cyclohexene 、 (4S)-(-)-4-tert-butylcyclohexene
  参考文献：
  名称：

  Enantioselective Preparation of 4-Substituted Cyclohexenes by Radical Fragmentation of Sulfoxides

  摘要：

  [GRAPHICS]Radical fragmentation of o-bromophenyl sulfoxides is reported. Starting from enantiomerically pure material, 4-substituted cyclohexene derivatives have been prepared with enantiomeric excesses between 70% and 86%, The key step of the process is a diastereoselective abstraction of a hydrogen atom by the initial aryl radical. The highest enantiomeric exesses have been obtained in the presence of aluminum Lewis acids.

  DOI：

  10.1021/ol990859p
• 作为产物：
  描述：

  (R)-trans-2-bromophenyl 4-(tert-butyl)cyclohexyl sulfoxide 在 lithium diisopropyl amide 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-cis-2-bromophenyl 4-(tert-butyl)cyclohexyl sulfoxide
  参考文献：
  名称：

  Enantioselective Preparation of 4-Substituted Cyclohexenes by Radical Fragmentation of Sulfoxides

  摘要：

  [GRAPHICS]Radical fragmentation of o-bromophenyl sulfoxides is reported. Starting from enantiomerically pure material, 4-substituted cyclohexene derivatives have been prepared with enantiomeric excesses between 70% and 86%, The key step of the process is a diastereoselective abstraction of a hydrogen atom by the initial aryl radical. The highest enantiomeric exesses have been obtained in the presence of aluminum Lewis acids.

  DOI：

  10.1021/ol990859p