Acetic acid (3aS,4aR,7aS,8R,8aS)-6,6-diethyl-8-hydroxy-2,2-dimethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester | 244231-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (3aS,4aR,7aS,8R,8aS)-6,6-diethyl-8-hydroxy-2,2-dimethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester
• CAS: 244231-07-0
• 化学式: C₁₇H₂₈O₇
• 分子量: 344.405
• InChiKey: NWBVINBEUPLDIB-FAHYXWLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aS,4aR,7aS,8R,8aS)-6,6-diethyl-8-hydroxy-2,2-dimethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到[(1S,3R,7R,9R)-5,5-diethyl-11,11-dimethyl-8-oxo-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecan-1-yl]methyl acetate
  参考文献：
  名称：

  A Class of C₂ and Pseudo C₂ Symmetric Ketone Catalysts for Asymmetric Epoxidation. Conformational Effect on Catalysis

  摘要：

  A class of C-2 and pseudo C-2 symmetric ketones with one fused ring at each side of the carbonyl group have been prepared from quinic acid and found to be effective catalysts for the asymmetric epoxidation of a variety of olefins. Electron deficient olefins such as enones can be efficiently epoxidized. Encouragingly good enantioselectivity is also obtained for the epoxidation of styrenes. The studies show that the ketone conformation plays an important role in the reactivity and selectivity of the catalyst.

  DOI：

  10.1021/jo9908849
• 作为产物：
  描述：

  methyl (3aR,7S,7aS)-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate 在 咪唑 、 4-二甲氨基吡啶 、 四氧化锇 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 二异丁基氢化铝 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 16.0h， 生成 Acetic acid (3aS,4aR,7aS,8R,8aS)-6,6-diethyl-8-hydroxy-2,2-dimethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester
  参考文献：
  名称：

  A Class of C₂ and Pseudo C₂ Symmetric Ketone Catalysts for Asymmetric Epoxidation. Conformational Effect on Catalysis

  摘要：

  A class of C-2 and pseudo C-2 symmetric ketones with one fused ring at each side of the carbonyl group have been prepared from quinic acid and found to be effective catalysts for the asymmetric epoxidation of a variety of olefins. Electron deficient olefins such as enones can be efficiently epoxidized. Encouragingly good enantioselectivity is also obtained for the epoxidation of styrenes. The studies show that the ketone conformation plays an important role in the reactivity and selectivity of the catalyst.

  DOI：

  10.1021/jo9908849