methyl (1R,3R,7R,8R,9S)-8-[tert-butyl(dimethyl)silyl]oxy-11,11-diethyl-5,5-dimethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecane-1-carboxylate | 244230-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R,3R,7R,8R,9S)-8-[tert-butyl(dimethyl)silyl]oxy-11,11-diethyl-5,5-dimethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecane-1-carboxylate
• CAS: 244230-96-4
• 化学式: C₂₂H₄₀O₇Si
• 分子量: 444.641
• InChiKey: KCZJZZQUYJVJMN-GQTOQBHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (1R,3R,7R,8R,9S)-8-[tert-butyl(dimethyl)silyl]oxy-11,11-diethyl-5,5-dimethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecane-1-carboxylate 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 [(1S,3R,7S,8R,9S)-11,11-diethyl-8-hydroxy-5,5-dimethyl-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：

  右旋奎宁酸 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 camphor-10-sulfonic acid 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 pyridinium chlorochromate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 51.5h， 生成 methyl (1R,3R,7R,8R,9S)-8-[tert-butyl(dimethyl)silyl]oxy-11,11-diethyl-5,5-dimethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecane-1-carboxylate
  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

文献信息

• A Class of <i>C</i><i>₂</i> and Pseudo <i>C</i><i>₂</i> Symmetric Ketone Catalysts for Asymmetric Epoxidation. Conformational Effect on Catalysis
  作者：Zhi-Xian Wang、Susie M. Miller、Oren P. Anderson、Yian Shi

  DOI：10.1021/jo9908849

  日期：1999.8.1

  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.