(R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone | 154699-07-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone
• CAS: 154699-07-7
• 化学式: C₂₄H₃₂O₂SSi
• 分子量: 412.668
• InChiKey: LQHMCZOMNHLGQL-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.77
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone 在 2,6-二甲基吡啶 、 palladium diacetate 、 cerium(III) chloride 、 三苯胂 、 Raney Ni(W₂) 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 9.75h， 生成 (1S,3R)-3-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-1,3-dimethyl-2-methylidenecyclopentanol
  参考文献：
  名称：

  A remarkable substituent effect on the enantioselectivity of tandem asymmetric epoxidation and enantiospecific ring expansion of cyclopropylidene alcohols: a new enantiocontrolled synthesis of (-)-debromoaplysin and (-)-aplysin

  摘要：

  A remarkable substituent effect by the tert-butyldimethylsiloxy group on the enantioselectivity of the tandem asymmetric epoxidation and enantiospecific ring expansion of 2-[2-(tert-butyldimethylsiloxy)-4-methylphenyl]-2-cyclopropylideneethanol (18), affording (S)-(-)-2-[2-(tert-butyldimethylsiloxy)-4-methylphenyl]-2-hydroxymethylcyclobutanone (21) in high yield and high enantiomeric excess, was observed. This enabled us to accomplish a concise and highly enantioselective total synthesis of (-)-debromoaplysin (2) and (-)-aplysin (1), providing a new and general strategy for the enantioselective synthesis of biologically important substances having the dihydrobenzofuran framework.

  DOI：

  10.1021/jo00080a014
• 作为产物：
  描述：

  1-(tert-Butyldiphenylsiloxy)-2-cyclopropylidene-2-(2-hydroxy-4-methylphenyl)ethane 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 三丁基膦 、 四丁基氟化铵 、 二异丁基氢化铝 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.75h， 生成 (R)-(-)-2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-<(phenylthio)methyl>cyclobutanone
  参考文献：
  名称：

  A remarkable substituent effect on the enantioselectivity of tandem asymmetric epoxidation and enantiospecific ring expansion of cyclopropylidene alcohols: a new enantiocontrolled synthesis of (-)-debromoaplysin and (-)-aplysin

  摘要：

  A remarkable substituent effect by the tert-butyldimethylsiloxy group on the enantioselectivity of the tandem asymmetric epoxidation and enantiospecific ring expansion of 2-[2-(tert-butyldimethylsiloxy)-4-methylphenyl]-2-cyclopropylideneethanol (18), affording (S)-(-)-2-[2-(tert-butyldimethylsiloxy)-4-methylphenyl]-2-hydroxymethylcyclobutanone (21) in high yield and high enantiomeric excess, was observed. This enabled us to accomplish a concise and highly enantioselective total synthesis of (-)-debromoaplysin (2) and (-)-aplysin (1), providing a new and general strategy for the enantioselective synthesis of biologically important substances having the dihydrobenzofuran framework.

  DOI：

  10.1021/jo00080a014