(-)-8-phenylmenthyl (Z)-2-(benzoylamino)-3-(ethoxycarbonyloxy)acrylate | 878560-00-0

• 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: (-)-8-phenylmenthyl (Z)-2-(benzoylamino)-3-(ethoxycarbonyloxy)acrylate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (Z)-2-benzamido-3-ethoxycarbonyloxyprop-2-enoate
• CAS: 878560-00-0
• 化学式: C₂₉H₃₅NO₆
• 分子量: 493.6
• InChiKey: WIJKNOAFMAIMOK-NAHUABNISA-N

物化性质

• 熔点：
  133 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  629.8±55.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-8-phenylmenthyl (Z)-2-(benzoylamino)-3-(ethoxycarbonyloxy)acrylate 在 palladium on activated charcoal 吡啶 、 magnesium(II) perchlorate 、 水 、 氢气 、 sodium carbonate 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 91.0h， 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：

  4-hydroxymethylene-2-phenyl-2-oxazolin-5-one 在 双(二丁基氯基锡(四))氧化物 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 27.0h， 生成 (-)-8-phenylmenthyl (Z)-2-(benzoylamino)-3-(ethoxycarbonyloxy)acrylate
  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

文献信息

• Enantioselective synthesis of epimeric cis-3-carboxycyclopentylglycines
  作者：Francesco Caputo、Francesca Clerici、Maria Luisa Gelmi、Sara Pellegrino、Tullio Pilati

  DOI：10.1016/j.tetasy.2005.11.011

  日期：2006.1

  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.