Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid,3-[[[(1S)-2-(1,1-dimethylethoxy)-2-oxo-1-(phenylmethyl)ethyl]amino]carbonyl]-, phenylmethyl ester, (1R,2S,3R,4S)- | 660439-21-4

• 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: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid,3-[[[(1S)-2-(1,1-dimethylethoxy)-2-oxo-1-(phenylmethyl)ethyl]amino]carbonyl]-, phenylmethyl ester, (1R,2S,3R,4S)-
• 英文别名: (2S,3R)-3-endo-(1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid benzyl ester
• CAS: 660439-21-4
• 化学式: C₂₉H₃₃NO₅
• 分子量: 475.585
• InChiKey: QUXAJSLPRYIUKY-MQZWXTIWSA-N

物化性质

• 沸点：
  629.7±55.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid,3-[[[(1S)-2-(1,1-dimethylethoxy)-2-oxo-1-(phenylmethyl)ethyl]amino]carbonyl]-, phenylmethyl ester, (1R,2S,3R,4S)- 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 13.0h， 生成 (2S,3R)-2-{[3-endo-(1-(tert-butoxycarbonyl)-2-phenylethylcarbamoyl)bicyclo[2.2.1]heptane-2-endo-carbonyl]amino}-4-methylpentanoic acid benzyl ester
  参考文献：
  名称：

  General Synthesis of Unsymmetrical Norbornane Scaffolds as Inducers for Hydrogen Bond Interactions in Peptides^,

  摘要：

  Starting from readily accessible endo-cis-(2S,3R)-norbornene dicarboxylic acid benzyl monoester, a general and efficient synthetic approach toward unsymmetrical two-stranded peptidic structures was developed. In these structures the peptide strands are oriented in a parallel geometry. Their synthesis is easily applicable to a variety of amino acids and peptides. Specifically, a norbornane template as molecular scaffold induces hydrogen bonding between the adjacent peptide strands. The specific hydrogen bonding patterns between these strands were revealed by detailed NMR analysis including TOCSY/NOE experiments.

  DOI：

  10.1021/jo030295+
• 作为产物：
  描述：

  L-苯基丙氨酸叔丁酯 、 (2R,3S)-3-endo-benzyloxycarbonyl-bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以85%的产率得到Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid,3-[[[(1S)-2-(1,1-dimethylethoxy)-2-oxo-1-(phenylmethyl)ethyl]amino]carbonyl]-, phenylmethyl ester, (1R,2S,3R,4S)-
  参考文献：
  名称：

  General Synthesis of Unsymmetrical Norbornane Scaffolds as Inducers for Hydrogen Bond Interactions in Peptides^,

  摘要：

  Starting from readily accessible endo-cis-(2S,3R)-norbornene dicarboxylic acid benzyl monoester, a general and efficient synthetic approach toward unsymmetrical two-stranded peptidic structures was developed. In these structures the peptide strands are oriented in a parallel geometry. Their synthesis is easily applicable to a variety of amino acids and peptides. Specifically, a norbornane template as molecular scaffold induces hydrogen bonding between the adjacent peptide strands. The specific hydrogen bonding patterns between these strands were revealed by detailed NMR analysis including TOCSY/NOE experiments.

  DOI：

  10.1021/jo030295+