(2S,3aR,8aR)-5-Hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester | 150852-18-9

• 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: (2S,3aR,8aR)-5-Hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester
• CAS: 150852-18-9
• 化学式: C₁₄H₁₆N₂O₅
• 分子量: 292.291
• InChiKey: WYJZXGHCEQSPHU-ADEWGFFLSA-N

物化性质

• 沸点：
  451.7±45.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  88.1
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3aR,8aR)-5-Hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester 在 吡啶 、 lithium diisopropyl amide 作用下， 生成 (2R,3aR,8aS)-8-Benzenesulfonyl-5-benzenesulfonyloxy-2-(2-trimethylsilanyl-ethoxymethyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of a-Substituted 5-Hydroxytryptophan Derivatives

  摘要：

  5-hydroxytryptophan was converted to pyrroloindole (3), which on deprotonation with LDA and subsequent reaction with alkyl halides gave the C-2 alkylated derivatives (6-9) cleanly with retention of configuration. Reversion to the 5-hydroxytryptophan skeleton was then achieved by stirring in trifluoroacetic acid and deprotection by treatment with sodium in liquid ammonia followed by saponification.

  DOI：

  10.3987/com-92-6313
• 作为产物：
  描述：

  methyl (S)-3-(5-hydroxy-1H-indol-3-yl)-2-((methoxycarbonyl)amino)propanoate 在 磷酸 作用下， 生成 (2S,3aR,8aR)-5-Hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of a-Substituted 5-Hydroxytryptophan Derivatives

  摘要：

  5-hydroxytryptophan was converted to pyrroloindole (3), which on deprotonation with LDA and subsequent reaction with alkyl halides gave the C-2 alkylated derivatives (6-9) cleanly with retention of configuration. Reversion to the 5-hydroxytryptophan skeleton was then achieved by stirring in trifluoroacetic acid and deprotection by treatment with sodium in liquid ammonia followed by saponification.

  DOI：

  10.3987/com-92-6313

文献信息

• Taniguchi, Mikio; Anjiki, Tomiko; Nakagawa, Masako, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 7, p. 2544 - 2554
  作者：Taniguchi, Mikio、Anjiki, Tomiko、Nakagawa, Masako、Hino, Tohru

  DOI：——

  日期：——