benzyl ((1R,2R)-2-hydroxycycloheptyl)carbamate | 1448438-55-8

• 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: benzyl ((1R,2R)-2-hydroxycycloheptyl)carbamate
• 英文别名: benzyl N-[(1R,2R)-2-hydroxycycloheptyl]carbamate
• CAS: 1448438-55-8
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: AMGAYIMPQQNONB-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氯甲酸苄酯 在 palladium 10% on activated carbon 、 (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 、 氢气 、 4-二甲氨基苯甲酸 、 1,8-双二甲氨基萘 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 45.17h， 生成 benzyl ((1R,2R)-2-hydroxycycloheptyl)carbamate
  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