(+)-menthyl 2'-chloro-hippurate | 159043-72-8

• 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: (+)-menthyl 2'-chloro-hippurate
• CAS: 159043-72-8
• 化学式: C₁₉H₂₆ClNO₃
• 分子量: 351.873
• InChiKey: WNUXEEBNFKUVPR-VBQJREDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+)-menthyl 2'-chloro-hippurate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 0.75h， 以97%的产率得到(+)-menthyl-2-bromo-2-chloro-hippurate
  参考文献：
  名称：

  Elucidation of the stereochemistry of the ?-amidoalkylation products resulting from the interaction of allyltrimethylsilane with electrophilic glycine menthyl ester derivatives

  摘要：

  Alpha-Amidoalkylation of allyltrimethylsilane with (-)- and (+)-menthyl-2-(o-Chlorobenzoylamino)-2-halogenoethanoate (2, 4a and 4b) gave in the presence of zinc chloride. separable mixtures of the diastereomers (-)- and (+)-menthyl-2-(o-Chlorobenzoylamino)-4-pentenoate (5a, 5b and 6a, 6b). The absolute configurations of 5a, 5b and 6a, 6b were determined through conversion of 5a into S-(+)-norvaline hydrochloride.

  DOI：

  10.1002/prac.19943360410
• 作为产物：
  描述：

  2-氯苯甲酰氨基乙酸 、 D-薄荷醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以85%的产率得到(+)-menthyl 2'-chloro-hippurate
  参考文献：
  名称：

  Elucidation of the stereochemistry of the ?-amidoalkylation products resulting from the interaction of allyltrimethylsilane with electrophilic glycine menthyl ester derivatives

  摘要：

  Alpha-Amidoalkylation of allyltrimethylsilane with (-)- and (+)-menthyl-2-(o-Chlorobenzoylamino)-2-halogenoethanoate (2, 4a and 4b) gave in the presence of zinc chloride. separable mixtures of the diastereomers (-)- and (+)-menthyl-2-(o-Chlorobenzoylamino)-4-pentenoate (5a, 5b and 6a, 6b). The absolute configurations of 5a, 5b and 6a, 6b were determined through conversion of 5a into S-(+)-norvaline hydrochloride.

  DOI：

  10.1002/prac.19943360410