(1'R,3'R,4'S)-8'-phenylmenthyl (1R,2S,4R)-2-acetylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylate | 905733-13-3

• 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: (1'R,3'R,4'S)-8'-phenylmenthyl (1R,2S,4R)-2-acetylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (1R,2S,4R)-2-acetamidobicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 905733-13-3
• 化学式: C₂₆H₃₅NO₃
• 分子量: 409.569
• InChiKey: YMHBQDPTQGTYNR-YTOLCRLSSA-N

物化性质

• 熔点：
  230 °C(Solv: acetone (67-64-1))
• 沸点：
  553.1±50.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'R,3'R,4'S)-8'-phenylmenthyl (1R,2S,4R)-2-acetylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylate 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 反应 8.0h， 以97%的产率得到(1R,3R,4S)-8-phenylmenthyl (1S,2S,4R,5R,6S)-2-acetylamino-5,6-dihydroxybicyclo[2.2.1]heptane-2-carboxylate
  参考文献：
  名称：

  α，γ-二氨基酸：新的受约束的6-氨基-3-氮杂双环[3.2.1]辛烷-6-羧酸的不对称合成

  摘要：

  合成两种新的非对映异构的6-氨基-3-氮杂双环[3.2.1]辛烷-6-羧酸外切-和内- 8，9是使用报道外切和内切降冰片烯氨基酸作为手性结构单元。该方法提供了对光学纯氨基酸8和9的快速访问，这些氨基酸既可以视为具有空间限制并以α，α-二取代为特征的α，γ-和α，δ-二氨基酸。

  DOI：

  10.1021/jo061391o
• 作为产物：
  描述：

  2-乙酰氨基丙烯酸 在 magnesium(II) perchlorate 、 双(二丁基氯基锡(四))氧化物 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 38.0h， 生成 (1'R,3'R,4'S)-8'-phenylmenthyl (1R,2S,4R)-2-acetylamino-bicyclo[2.2.1]hept-5-ene-2-carboxylate
  参考文献：
  名称：

  An efficient synthesis of new diastereomeric enantiopure 1-aminocyclopentane-1,2,4-tricarboxylic acids

  摘要：

  Novel 1-aminocyclopentane-1,2,4-tricarboxylic acids 11 and 14 containing the glutamic acid skeleton were prepared as two diastereomers characterized by having the carbonyl groups in positions two and four cis to each other and trans with respect to the 1-carboxylic group and as all cis relationship, respectively. The reaction sequences, that is, Diels-Alder reaction to give norbornene cycloadducts, oxidative cleavage of the double bond of the cycloadducts, ensured the proper stereochemistry of both diastereomers. Each diastereomer was prepared in enantiopure form starting from exo- and endo-2-amino-norbornene-2-carboxylic acid derivatives 5 and 6 obtained through a very efficient asymmetric synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.05.001

文献信息

• An efficient synthesis of new diastereomeric enantiopure 1-aminocyclopentane-1,2,4-tricarboxylic acids
  作者：Francesco Caputo、Francesca Clerici、Maria Luisa Gelmi、Sara Pellegrino、Donato Pocar

  DOI：10.1016/j.tetasy.2006.05.001

  日期：2006.5

  Novel 1-aminocyclopentane-1,2,4-tricarboxylic acids 11 and 14 containing the glutamic acid skeleton were prepared as two diastereomers characterized by having the carbonyl groups in positions two and four cis to each other and trans with respect to the 1-carboxylic group and as all cis relationship, respectively. The reaction sequences, that is, Diels-Alder reaction to give norbornene cycloadducts, oxidative cleavage of the double bond of the cycloadducts, ensured the proper stereochemistry of both diastereomers. Each diastereomer was prepared in enantiopure form starting from exo- and endo-2-amino-norbornene-2-carboxylic acid derivatives 5 and 6 obtained through a very efficient asymmetric synthesis. (c) 2006 Elsevier Ltd. All rights reserved.
• α,γ-Diamino Acids:  Asymmetric Synthesis of New Constrained 6-Amino-3-azabicyclo[3.2.1]octane-6-carboxylic Acids
  作者：Francesco Caputo、Cristian Cattaneo、Francesca Clerici、Maria Luisa Gelmi、Sara Pellegrino

  DOI：10.1021/jo061391o

  日期：2006.10.1

  The synthesis of two new diastereomeric 6-amino-3-azabicyclo[3.2.1]octane-6-carboxylic acids exo- and endo-8,9 is reported using exo- and endo-norbornene amino acids as chiral building blocks. This method provides a fast access to optically pure amino acids 8 and 9 which can be considered both α,γ- and α,δ-diamino acids containing sterical constraints and characterized by α,α-disubstitution.

  合成两种新的非对映异构的6-氨基-3-氮杂双环[3.2.1]辛烷-6-羧酸外切-和内- 8，9是使用报道外切和内切降冰片烯氨基酸作为手性结构单元。该方法提供了对光学纯氨基酸8和9的快速访问，这些氨基酸既可以视为具有空间限制并以α，α-二取代为特征的α，γ-和α，δ-二氨基酸。