(-)-8-phenylmenthyl (1R,2R,3S,4S)-2-(benzoylamino)-3-(ethoxycarbonyloxy)bicyclo[2.2.1]heptane-2-carboxylate | 878560-03-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-8-phenylmenthyl (1R,2R,3S,4S)-2-(benzoylamino)-3-(ethoxycarbonyloxy)bicyclo[2.2.1]heptane-2-carboxylate
• CAS: 878560-03-3
• 化学式: C₃₄H₄₃NO₆
• 分子量: 561.719
• InChiKey: NBGKBGYRNVAUQA-USBWRDSISA-N

物化性质

• 熔点：
  135 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  701.4±60.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (-)-8-phenylmenthyl (1R,2R,3S,4S)-2-(benzoylamino)-3-(ethoxycarbonyloxy)bicyclo[2.2.1]heptane-2-carboxylate 在 吡啶 、 水 、 sodium carbonate 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 (1S,3R,1'R) 3-(benzoylamino-ethoxycarbonylmethyl)cyclopentanecarboxylic acid
  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 2-(benzoylamino)-3-(ethoxycarbonyloxy)bicyclo[2.2.1]hept-5-ene-2-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 2.0h， 以96%的产率得到(-)-8-phenylmenthyl (1R,2R,3S,4S)-2-(benzoylamino)-3-(ethoxycarbonyloxy)bicyclo[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