(1R,2S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-cyclohexanecarboxylic acid methyl ester | 167281-08-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R,2S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-cyclohexanecarboxylic acid methyl ester
• CAS: 167281-08-5
• 化学式: C₁₆H₃₀O₄Si
• 分子量: 314.497
• InChiKey: LRSVNYDXJSUPCQ-IACUBPJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-cyclohexanecarboxylic acid methyl ester 在 camphor-10-sulfonic acid 、 4-甲基苯磺酸吡啶 作用下， 生成 (3S,3aS,7aR)-3-Methyl-tetrahydro-isobenzofuran-1,5-dione
  参考文献：
  名称：

  Internal activation of acrylate-type dienophiles in Diels-Alder reactions

  摘要：

  Diels-Alder reactions of less reactive acrylate-type dienophiles with dienes were achieved by replacing its ester counterpart to a pentafluorophenyl group, which remarkably enhanced the reactivity of the dienophiles to give the corresponding cycloadducts in excellent yields with a high stereoselectivity.

  DOI：

  10.1016/0040-4039(94)02379-p
• 作为产物：
  描述：

  (1R,2S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-cyclohexanecarboxylic acid pentafluorophenyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,2S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-cyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  Internal activation of acrylate-type dienophiles in Diels-Alder reactions

  摘要：

  Diels-Alder reactions of less reactive acrylate-type dienophiles with dienes were achieved by replacing its ester counterpart to a pentafluorophenyl group, which remarkably enhanced the reactivity of the dienophiles to give the corresponding cycloadducts in excellent yields with a high stereoselectivity.

  DOI：

  10.1016/0040-4039(94)02379-p