(-)-8-phenylmenthyl (1R,2R,3S,4S)-2-(benzoylamino)-3-hydroxybicyclo[2.2.1]heptane-2-carboxylate | 878560-04-4

• 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: (-)-8-phenylmenthyl (1R,2R,3S,4S)-2-(benzoylamino)-3-hydroxybicyclo[2.2.1]heptane-2-carboxylate
• CAS: 878560-04-4
• 化学式: C₃₁H₃₉NO₄
• 分子量: 489.655
• InChiKey: ILZRLOJMWLBGEC-DNVWXAOXSA-N

物化性质

• 熔点：
  202 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  652.7±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (-)-8-phenylmenthyl (1R,2R,3S,4S)-2-(benzoylamino)-3-hydroxybicyclo[2.2.1]heptane-2-carboxylate 在 吡啶 、 水 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Enantioselective synthesis of epimeric cis-3-carboxycyclopentylglycines

  摘要：

  Two epimeric chiral cyclopentylglycines (-)-16 and (+)-17, functionalised with a carboxy group cis to the amino acid group, were prepared starting from chiral 2-amino-3-oxo-norbornanecarboxylic acid derivative exo-9 by combining two classical reactions such as the Diels-Alder and retro-Claisen reactions. Compounds 16 and 17 are non-proteinogenic amino acids of biological interest containing conformational constraints in which the skeletons of both 2-aminoadipic acid and 2-aminopimelic acid are included. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.011
• 作为产物：
  描述：

  (-)-8-phenylmenthyl (1R,2R,3S,4S)-2-(benzoylamino)-3-(ethoxycarbonyloxy)bicyclo[2.2.1]heptane-2-carboxylate 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以95%的产率得到(-)-8-phenylmenthyl (1R,2R,3S,4S)-2-(benzoylamino)-3-hydroxybicyclo[2.2.1]heptane-2-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of epimeric cis-3-carboxycyclopentylglycines

  摘要：

  Two epimeric chiral cyclopentylglycines (-)-16 and (+)-17, functionalised with a carboxy group cis to the amino acid group, were prepared starting from chiral 2-amino-3-oxo-norbornanecarboxylic acid derivative exo-9 by combining two classical reactions such as the Diels-Alder and retro-Claisen reactions. Compounds 16 and 17 are non-proteinogenic amino acids of biological interest containing conformational constraints in which the skeletons of both 2-aminoadipic acid and 2-aminopimelic acid are included. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.011