(S)-2-{[(1S,2R)-2-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-cyclohexanecarbonyl]-amino}-3-phenyl-propionic acid benzyl ester | 184529-81-5

• 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: (S)-2-{[(1S,2R)-2-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-cyclohexanecarbonyl]-amino}-3-phenyl-propionic acid benzyl ester
• CAS: 184529-81-5
• 化学式: C₄₀H₄₂N₂O₆
• 分子量: 646.783
• InChiKey: QLJRDZXTBTUFEU-WLPVSNDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  48.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  110.8
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-{[(1S,2R)-2-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-cyclohexanecarbonyl]-amino}-3-phenyl-propionic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到(S)-2-{[(1S,2R)-2-((S)-1-Carboxy-2-phenyl-ethylcarbamoyl)-cyclohexanecarbonyl]-amino}-3-phenyl-propionic acid
  参考文献：
  名称：

  The influence of molecular conformation upon the self-assembly of cyclohexane diamide diacids

  摘要：

  Background: Information regarding the self-association of small peptide motifs can be used in the design of peptide microstructures. Previous work in our laboratories illustrated the self-association of certain diamide diacids into microcapsules. In this report a series of cyclohexane diamide diacids are investigated. The cyclohexylene (R-C6H10-R) system (with its axial and equatorial requirements) provided an opportunity to study the influence of molecular conformation upon the self-aggregation process.Results: Condensation of the respective cis- and trans-1,2-, 1,3-, and 1,4-cyclohexane dicarboxylic acid platforms with two equivalents of a L-Phe ester followed by deprotection gave the desired diamide diacids. Basic solutions of cis-1,2-,trans-1,3-, and cis-1,4-diamide diacids generated solid microspheres when acidified to pH 2.4 Molecular modeling revealed that 1,3-diaxial interactions favor a helical turn within these diamides.Conclusions: Access to 'complementary' molecular geometries is needed to self-associate into microscopic architectures. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00139-9
• 作为产物：
  描述：

  1,2-cis-cyclohexanedicarboxylic anhydride 在 N-甲基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 (S)-2-{[(1S,2R)-2-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-cyclohexanecarbonyl]-amino}-3-phenyl-propionic acid benzyl ester
  参考文献：
  名称：

  The influence of molecular conformation upon the self-assembly of cyclohexane diamide diacids

  摘要：

  Background: Information regarding the self-association of small peptide motifs can be used in the design of peptide microstructures. Previous work in our laboratories illustrated the self-association of certain diamide diacids into microcapsules. In this report a series of cyclohexane diamide diacids are investigated. The cyclohexylene (R-C6H10-R) system (with its axial and equatorial requirements) provided an opportunity to study the influence of molecular conformation upon the self-aggregation process.Results: Condensation of the respective cis- and trans-1,2-, 1,3-, and 1,4-cyclohexane dicarboxylic acid platforms with two equivalents of a L-Phe ester followed by deprotection gave the desired diamide diacids. Basic solutions of cis-1,2-,trans-1,3-, and cis-1,4-diamide diacids generated solid microspheres when acidified to pH 2.4 Molecular modeling revealed that 1,3-diaxial interactions favor a helical turn within these diamides.Conclusions: Access to 'complementary' molecular geometries is needed to self-associate into microscopic architectures. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00139-9