(1S,2S,3R)-2-benzyloxycarbonylamino-3-hydroxycyclohexyl 3-phenylpropanoate | 1448438-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,3R)-2-benzyloxycarbonylamino-3-hydroxycyclohexyl 3-phenylpropanoate
• 英文别名: [(1S,2S,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)cyclohexyl] 3-phenylpropanoate
• CAS: 1448438-58-1
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: WBWIQOHYDYVDMQ-URVUXULASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴-3-苯基丙醛 、 benzyl N-((1r,2R,6S)-2,6-dihydroxycyclohexyl)carbamate 在 (5aS,10bR)-9-nitro-2-phenyl-4,5a,6,10b-tetrahydroindeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate 、 4-二甲氨基苯甲酸 、 1,8-双二甲氨基萘 作用下， 以 氯仿 为溶剂， 反应 10.17h， 以98%的产率得到(1S,2S,3R)-2-benzyloxycarbonylamino-3-hydroxycyclohexyl 3-phenylpropanoate
  参考文献：
  名称：

  Enhanced Rate and Selectivity by Carboxylate Salt as a Basic Cocatalyst in Chiral N-Heterocyclic Carbene-Catalyzed Asymmetric Acylation of Secondary Alcohols

  摘要：

  The rate and enantioselectivity of chiral NHC-catalyzed asymmetric acylation of alcohols with an adjacent H-bond donor functionality are remarkably enhanced in the presence of a carboxylate cocatalyst. The degree of the enhancement is correlated with the basicity of the carboxylate. With a cocatalyst and a newly developed electron-deficient chiral NHC, kinetic resolution and desymmetrization of cyclic diols and amino alcohols were achieved with extremely high selectivity (up to s = 218 and 99% ee, respectively) at a low catalyst loading (0.5 mol %). This asymmetric acylation is characterized by a unique preference for alcohols over amines, which are not converted into amides under the reaction conditions.

  DOI：

  10.1021/ja4055838