α-N-benzyloxycarbonyl-β-(2,5-dimethoxyphenyl)tryptophan tert-butyl ester | 296235-56-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: α-N-benzyloxycarbonyl-β-(2,5-dimethoxyphenyl)tryptophan tert-butyl ester
• CAS: 296235-56-8
• 化学式: C₃₁H₃₄N₂O₆
• 分子量: 530.621
• InChiKey: AMEBRGSOBDKCRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  98.88
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  α-N-benzyloxycarbonyl-β-(2,5-dimethoxyphenyl)tryptophan tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 溶剂黄146 、 甲苯 为溶剂， 反应 5.0h， 生成 trans-(3S*,4R*)-4-(2,5-dimethoxyphenyl)-1,2,3,4-tetrahydrospiro[β-carboline-1,1'-cyclohexane]-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A Convenient Synthesis of Conformationally Constrained β-Substituted Tryptophans

  摘要：

  A short and general synthesis for the preparation of various conformationally constrained beta-substituted tryptophans has been elaborated starting from indole, aldehydes and Meldrum's acid by using trimolecular condensation and Curtius rearrangement mediated functional group transformations followed by deprotections, as key-steps. The relative configurations of the two diastereomeric series have been determined indirectly by the measurement of (3)J coupling constants in the corresponding tetrahydro-beta-carbolines, and further supported by means of molecular modelizations. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00446-4
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 在 二苯基磷酸 、 三乙胺 、 DL-脯氨酸 作用下， 以 吡啶 、 甲苯 、 乙腈 为溶剂， 反应 18.5h， 生成 α-N-benzyloxycarbonyl-β-(2,5-dimethoxyphenyl)tryptophan tert-butyl ester
  参考文献：
  名称：

  A Convenient Synthesis of Conformationally Constrained β-Substituted Tryptophans

  摘要：

  A short and general synthesis for the preparation of various conformationally constrained beta-substituted tryptophans has been elaborated starting from indole, aldehydes and Meldrum's acid by using trimolecular condensation and Curtius rearrangement mediated functional group transformations followed by deprotections, as key-steps. The relative configurations of the two diastereomeric series have been determined indirectly by the measurement of (3)J coupling constants in the corresponding tetrahydro-beta-carbolines, and further supported by means of molecular modelizations. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00446-4