(1R,2S,5R)-menthyl-2-(diphenylmethylideneamino)propenoate | 395074-01-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,5R)-menthyl-2-(diphenylmethylideneamino)propenoate
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-(benzhydrylideneamino)prop-2-enoate
• CAS: 395074-01-8
• 化学式: C₂₆H₃₁NO₂
• 分子量: 389.538
• InChiKey: PCWDVRUKLQUSQX-VEXUSMLFSA-N

物化性质

• 沸点：
  488.2±37.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-menthyl-2-(diphenylmethylideneamino)propenoate 在 盐酸 、 三丁基膦 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 18.0h， 生成 1-(1R,2S,5R)-menthyl 3-ethyl (1R)-1-benzyloxycarbonylamino-3-cyclopentenedicarboxylate
  参考文献：
  名称：

  Synthesis and Biological Activities of Conformationally Restricted Cyclopentenyl-Glutamate Analogues

  摘要：

  An efficient method for preparing conformationally restricted cyclopentenyl-glutamate analogues in a regioselective and diastereoselective manner has been developed using a formal [3 + 2] cycloaddition reaction of dehydroamino acids. Methods for preparing optically active versions of these compounds have also been devised. Of these compounds, (S)-2 is an agonist at the mGlu5 (EC50 18 muM) and mGlu2 (EC50 45 muM) receptors.

  DOI：

  10.1021/jo010864i
• 作为产物：
  描述：

  (1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>acetate 在 n,n-二甲基亚甲基碘化胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 130.5h， 生成 (1R,2S,5R)-menthyl-2-(diphenylmethylideneamino)propenoate
  参考文献：
  名称：

  Synthesis and Biological Activities of Conformationally Restricted Cyclopentenyl-Glutamate Analogues

  摘要：

  An efficient method for preparing conformationally restricted cyclopentenyl-glutamate analogues in a regioselective and diastereoselective manner has been developed using a formal [3 + 2] cycloaddition reaction of dehydroamino acids. Methods for preparing optically active versions of these compounds have also been devised. Of these compounds, (S)-2 is an agonist at the mGlu5 (EC50 18 muM) and mGlu2 (EC50 45 muM) receptors.

  DOI：

  10.1021/jo010864i