1-methoxycarbonyl-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole | 146062-18-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-methoxycarbonyl-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
• 英文别名: 1-Methoxycarbonyl-1-trifluoromethyl-1,2,3,4-tetrahydro-9h-pyrido[3,4-b]indole；methyl 1-(trifluoromethyl)-2,3,4,9-tetrahydropyrido[3,4-b]indole-1-carboxylate
• CAS: 146062-18-2
• 化学式: C₁₄H₁₃F₃N₂O₂
• 分子量: 298.265
• InChiKey: PVZUIGDLMHSPNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  色胺 、 三氟丙酮酸甲酯 以 乙腈 为溶剂， 反应 3.0h， 以81.6%的产率得到1-methoxycarbonyl-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
  参考文献：
  名称：

  Methyl trifluoropyruvate in the Pictet-Spengler reaction

  摘要：

  Condensation of methyl trifluoropyruvate with 2-(3,4-dimethoxyphenyl)ethylamine, tryptamine, and (D, L)-tryptophan yielded 1-methoxycarbonyl-1-trifluoromethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline, 1-methoxycarbonyl-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, and Z-1-methoxycarbonyl-1-trifluoromethyl-3-carboxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, respectively. The Z configuration of the latter was determined by x-ray structural analysis.

  DOI：

  10.1007/bf00864340

文献信息

• Methyl trifluoropyruvate in the Pictet-Spengler reaction
  作者：A. S. Golubev、N. D. Chkanikov、M. Yu. Antipin、Yu. T. Struchkov、A. F. Kolomiets、A. V. Fokin

  DOI：10.1007/bf00864340

  日期：1992.8

  Condensation of methyl trifluoropyruvate with 2-(3,4-dimethoxyphenyl)ethylamine, tryptamine, and (D, L)-tryptophan yielded 1-methoxycarbonyl-1-trifluoromethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline, 1-methoxycarbonyl-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, and Z-1-methoxycarbonyl-1-trifluoromethyl-3-carboxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, respectively. The Z configuration of the latter was determined by x-ray structural analysis.