(-)-8-phenylmenthyl 2-(benzoylamino)-3-(ethoxycarbonyloxy)bicyclo[2.2.1]hept-5-ene-2-carboxylate | 878560-01-1

• 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 2-(benzoylamino)-3-(ethoxycarbonyloxy)bicyclo[2.2.1]hept-5-ene-2-carboxylate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (1S,2R,3S,4R)-2-benzamido-3-ethoxycarbonyloxybicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 878560-01-1
• 化学式: C₃₄H₄₁NO₆
• 分子量: 559.703
• InChiKey: NRKXGJGWOQGKBU-USBWRDSISA-N

物化性质

• 沸点：
  702.0±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 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 2-(benzoylamino)-3-(ethoxycarbonyloxy)bicyclo[2.2.1]hept-5-ene-2-carboxylate 在 palladium on activated charcoal 吡啶 、 水 、 氢气 、 sodium carbonate 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 55.0h， 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 (Z)-2-(benzoylamino)-3-hydroxyacrylate 在 magnesium(II) perchlorate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 39.0h， 生成 (-)-8-phenylmenthyl 2-(benzoylamino)-3-(ethoxycarbonyloxy)bicyclo[2.2.1]hept-5-ene-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

文献信息

• β-Hydroxynorbornane amino acid derivatives: valuable synthons for the diastereoselective preparation of substituted cyclopentylglycine derivatives
  作者：Sara Pellegrino、Francesca Clerici、Maria Luisa Gelmi

  DOI：10.1016/j.tet.2008.04.038

  日期：2008.6

  The behaviour towards the retro-aldol or retro-Dieckmann reactions of several norbornene and norbornane amino acids functionalized with an oxygen atom at C-β and characterized by different features, such as the substitution pattern and the constraints, was investigated. By C2–C3 disconnection new differently functionalized cyclopentenyl- and cyclopentylglycines were prepared. This synthetic approach

  研究了在C-β处被氧原子官能化并具有不同特征（例如取代模式和限制条件）的几种降冰片烯和降冰片烷氨基酸对逆醛醇或逆Dieckmann反应的行为。通过C 2 -C 3断开，制备了新的不同官能的环戊烯基和环戊基甘氨酸。该合成方法允许根据起始降冰片烷衍生物将立体化学控制在两个到四个立体中心，并为每个衍生物在氨基酸立体中心提供一对差向异构化合物。取决于起始试剂的特征和反应条件，氨基酸碳原子的立体化学的部分控制也是可能的。