(4R,5R,6S)-6-Bromo-4-hydroxy-5-methyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohex-2-enone | 208447-85-2

• 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: (4R,5R,6S)-6-Bromo-4-hydroxy-5-methyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohex-2-enone
• CAS: 208447-85-2
• 化学式: C₁₅H₁₇BrO₃S
• 分子量: 357.268
• InChiKey: VTNIQOVYPUSZSG-MRQYSOIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4R,5R,6S)-6-Bromo-4-hydroxy-5-methyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohex-2-enone 在 lithium carbonate 、 lithium bromide 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (R)-4-Ethyl-2-methyl-1-((R)-toluene-4-sulfinylmethyl)-cyclohexa-2,5-diene-1,4-diol
  参考文献：
  名称：

  Studies of Diastereoselectivity in Conjugate Addition of Organoaluminum Reagents to (R)-[(p-Tolylsulfinyl)methyl]quinols and Derivatives

  摘要：

  (R)-4-Hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienones 1-3, and 6 reacted with organoaluminum derivatives from the pro-R conjugated position in a highly pi-facial diastereoselective manner directed by the C-4 OH. A similar facial diastereoselectivity arose from reactions with 3-alkyl-substituted analogues 4 and 5 and 5-alkyl-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2-cyclohexenones 10a,b. Semiempirical calculations (AM1 model) provide data on transition-state energies for additions in full agreement with the experimental results.

  DOI：

  10.1021/jo980084i
• 作为产物：
  描述：

  三甲基铝 、 [(S)R]-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienone 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 (4R,5R,6S)-6-Bromo-4-hydroxy-5-methyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohex-2-enone 、 (4R,5R,6R)-6-Bromo-4-hydroxy-5-methyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohex-2-enone
  参考文献：
  名称：

  Studies of Diastereoselectivity in Conjugate Addition of Organoaluminum Reagents to (R)-[(p-Tolylsulfinyl)methyl]quinols and Derivatives

  摘要：

  (R)-4-Hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienones 1-3, and 6 reacted with organoaluminum derivatives from the pro-R conjugated position in a highly pi-facial diastereoselective manner directed by the C-4 OH. A similar facial diastereoselectivity arose from reactions with 3-alkyl-substituted analogues 4 and 5 and 5-alkyl-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2-cyclohexenones 10a,b. Semiempirical calculations (AM1 model) provide data on transition-state energies for additions in full agreement with the experimental results.

  DOI：

  10.1021/jo980084i