(+/-)-Nb-acetyl-5-hydroxytryptophan methyl ester | 52068-33-4

• 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: (+/-)-Nb-acetyl-5-hydroxytryptophan methyl ester
• 英文别名: methyl 2-acetamido-3-(5-hydroxy-1H-indol-3-yl)propanoate
• CAS: 52068-33-4
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: BHZJFKVBLAUKAX-UHFFFAOYSA-N

物化性质

• 沸点：
  573.9±50.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-Nb-acetyl-5-hydroxytryptophan methyl ester 在 亚碘酰苯 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以39%的产率得到(+/-)-Nb-acetyltryptophan-4,5-dione methyl ester
  参考文献：
  名称：

  Nucleophilic Substitution Reaction of 1-Hydroxytryptophan and 1-Hydroxytryptamine Derivatives (Regioselective Syntheses of 5-Substituted Derivatives of Tryptophane and Tryptamine)

  摘要：

  Regioselective nucleophilic substitution at the 5-position of indole nucleus was observed in the reaction of 1-hydroxytryptophan and 1-hydroxytryptamine derivatives with acids, suggesting the mechanism of serotonin formation in the central nervous system.

  DOI：

  10.3987/com-93-6391
• 作为产物：
  描述：

  甲酸 、 (+/-)-Nb-acetyl-1-hydroxytryptophan methyl ester 反应 45.0h， 以40%的产率得到(+/-)-Nb-acetyl-1-formyl-5-hydroxytryptophan methyl ester
  参考文献：
  名称：

  Nucleophilic Substitution Reaction of 1-Hydroxytryptophan and 1-Hydroxytryptamine Derivatives (Regioselective Syntheses of 5-Substituted Derivatives of Tryptophane and Tryptamine)

  摘要：

  Regioselective nucleophilic substitution at the 5-position of indole nucleus was observed in the reaction of 1-hydroxytryptophan and 1-hydroxytryptamine derivatives with acids, suggesting the mechanism of serotonin formation in the central nervous system.

  DOI：

  10.3987/com-93-6391

文献信息

• Preparations of Tryptamine-4,5-dinones, and Their Diels-Alder and Nucleophilic Addition Reactions
  作者：Masanori Somei、Yoshikazu Fukui、Masakazu Hasegawa

  DOI：10.3987/com-95-7189

  日期：——

  Syntheses of Nb-acetyltryptamine-4,5-dione and (+/-)-Nb-acetyltryptophan-4,5-dione methyl ester are reported. They were excellent dienophiles as well as good electrophiles, and produced 6,7-disubstituted indoles in Diels-Alder reaction and various 7-substituted indoles with nucleophiles.
• US4001276A
  申请人：——

  公开号：US4001276A

  公开（公告）日：1977-01-04
• Nucleophilic Substitution Reaction of 1-Hydroxytryptophan and 1-Hydroxytryptamine Derivatives (Regioselective Syntheses of 5-Substituted Derivatives of Tryptophane and Tryptamine)
  作者：Masanori Somei、Yoshikazu Fukui

  DOI：10.3987/com-93-6391

  日期：——

  Regioselective nucleophilic substitution at the 5-position of indole nucleus was observed in the reaction of 1-hydroxytryptophan and 1-hydroxytryptamine derivatives with acids, suggesting the mechanism of serotonin formation in the central nervous system.