trans-2-hydroxycyclohexyl diphenyl phosphate | 72216-36-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: trans-2-hydroxycyclohexyl diphenyl phosphate
• 英文别名: Phosphoric acid, 2-hydroxycyclohexyl diphenyl ester, trans-；[(1R,2R)-2-hydroxycyclohexyl] diphenyl phosphate
• CAS: 72216-36-5
• 化学式: C₁₈H₂₁O₅P
• 分子量: 348.336
• InChiKey: NHBIXTXJNPWATG-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  trans-1,2-cyclohexandiol 、 氯磷酸二苯酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以33.2%的产率得到trans-2-hydroxycyclohexyl diphenyl phosphate
  参考文献：
  名称：

  Lipophilic Oligopeptides for Chemo- and Enantioselective Acyl Transfer Reactions onto Alcohols

  摘要：

  Inspired by the extraordinary selectivities of acylases, we envisioned the use of lipophilic oligopeptidic organocatalysts for the acylative kinetic resolution/desymmetrization of rac- and meso-cycloalkane-1,2-diols. Here we describe in a full account the discovery and development process from the theoretical concept to the final catalyst, including scope and limitations. Competition experiments with various alcohols and electrophiles show the full potential of the employed oligopeptides. Additionally, we utilized NMR and IR-spectroscopic methods as well as computations to shed light on the factors responsible for the selectivity. The catalyst system can be readily modified to a multicatalyst by adding other catalytically active amino acids to the peptide backbone, enabling the stereoselective one-pot synthesis of complex molecules from simple starting materials.

  DOI：

  10.1021/jo401195c