cis-2-(2,2,2-trichloroacetoxy)cyclohexyl isobutyrate | 1228440-24-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-2-(2,2,2-trichloroacetoxy)cyclohexyl isobutyrate
• 英文别名: [(1S,2R)-2-(2,2,2-trichloroacetyl)oxycyclohexyl] 2-methylpropanoate
• CAS: 1228440-24-1
• 化学式: C₁₂H₁₇Cl₃O₄
• 分子量: 331.624
• InChiKey: GKAZKIOAQFNIPH-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  cis-2-hydroxycyclohexyl 2,2,2-trichloroacetate 、 异丁酸酐 在 methyl (S)-2-(3,5-di-tert-butylphenylthioamido)-3-(1-methyl-1H-imidazol-5-yl)propanoate 、 N,N-二异丙基乙胺 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 生成 cis-2-(2,2,2-trichloroacetoxy)cyclohexyl isobutyrate 、 cis-2-(2,2,2-trichloroacetoxy)cyclohexyl isobutyrate
  参考文献：
  名称：

  Desymmetrization of meso-1,2-Diols via the Dynamic Kinetic Resolution of Its Monodichloroacetates

  摘要：

  Enantioselective acylation catalyzed by the thioamide modified 1-methylhistidine methyl ester 1 in combination with DABCO-mediated racemization of the substrate led to the efficient dynamic kinetic resolution or meso-1,2-diol monodichloroacetates. In this way, cyclic and acyclic meso-1,2-diol monodichloroacetates can be transformed to the enantiomerically enriched (1S,2R)-heterosubstituted diol diesters which are stable in enantiomerically pure form and can be readily used for further organic transformations.

  DOI：

  10.1021/jo100435f

文献信息

• Desymmetrization of <i>meso</i>-1,2-Diols via the Dynamic Kinetic Resolution of Its Monodichloroacetates
  作者：Jin-Li Cao、Jin Qu

  DOI：10.1021/jo100435f

  日期：2010.6.4

  Enantioselective acylation catalyzed by the thioamide modified 1-methylhistidine methyl ester 1 in combination with DABCO-mediated racemization of the substrate led to the efficient dynamic kinetic resolution or meso-1,2-diol monodichloroacetates. In this way, cyclic and acyclic meso-1,2-diol monodichloroacetates can be transformed to the enantiomerically enriched (1S,2R)-heterosubstituted diol diesters which are stable in enantiomerically pure form and can be readily used for further organic transformations.