6-methoxytryptamine-2-carboxylic acid | 20731-72-0

• 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: 6-methoxytryptamine-2-carboxylic acid
• 英文别名: 3-(2-azaniumylethyl)-6-methoxy-1H-indole-2-carboxylate
• CAS: 20731-72-0
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: BMXXBEUPHOWECR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methoxytryptamine-2-carboxylic acid 在 盐酸 作用下， 生成 3-(2-氨基乙基)-6-甲氧基吲哚
  参考文献：
  名称：

  881.色胺，咔啉和相关化合物。第三部分 1-甲基-和1：N-二甲基-色胺

  摘要：

  DOI：

  10.1039/jr9560004593
• 作为产物：
  描述：

  哈尔马拉西定碱 在 氢氧化钾 作用下， 以90%的产率得到6-methoxytryptamine-2-carboxylic acid
  参考文献：
  名称：

  Carboxyl-mediated Pictet-Spengler reaction. Direct synthesis of 1,2,3,4-tetrahydro-.beta.-carbolines from tryptamine-2-carboxylic acids

  摘要：

  The Pictet-Spengler condensation of various tryptamine-2-carboxylic acids 9a-f with carbonyl compounds in benzene/dioxane/trifluoroacetic acid (Table I) with simultaneous loss of carbon dioxide afforded directly the corresponding 1,2,3,4-tetrahydro-beta-carbolines 14a-j in good to excellent yields. This reaction greatly enhances the use of the Abramovitch-Shapiro method for the synthesis of highly oxygenated ring A substituted 1,2,3,4-tetrahydro-beta-carbolines (THBC). The lactams 14f,g and 14h are key intermediates for the synthesis of ring A substituted 1-methoxycanthin-6-one analogues.

  DOI：

  10.1021/jo00001a066

文献信息

• Carboxyl-mediated pictet-spengler reaction. Direct synthesis of 1,2,3,4-tetrahydro β-carbolines from tryptamine-2-carboxylic acids.
  作者：Krishnaswamy Narayanan、James M Cook

  DOI：10.1016/s0040-4039(00)97406-9

  日期：1990.1

  The Pictet-Spengler condensation of various tryptamine-2-carboxylic acids 1 with carbonyl compounds in benzene/dioxane/trifiuoroacetic acid (Table) with simultaneous loss of carbon dioxide, afforded directly the corresponding 1,2,3,4-tetrahydro β-carbolines 4 in good to excellent yields.

  各种色胺2-羧酸1与羰基化合物在苯/二恶烷/三氟乙酸中的Pictet-Spengler缩合反应（表），同时损失了二氧化碳，直接得到相应的1,2,3,4-四氢β-咔啉4优良至极佳的产量。
• NARAYANAN, KRISHNASWAMY;COOK, JAMES M., TETRAHEDRON LETT., 31,(1990) N4, C. 3397-3400
  作者：NARAYANAN, KRISHNASWAMY、COOK, JAMES M.

  DOI：——

  日期：——
• NARAYANAN, KRISHNASWAMY;SCHINDLER, LIESL;COOK, JAMES M., J. ORG. CHEM., 56,(1991) N, C. 359-365
  作者：NARAYANAN, KRISHNASWAMY、SCHINDLER, LIESL、COOK, JAMES M.

  DOI：——

  日期：——
• Carboxyl-mediated Pictet-Spengler reaction. Direct synthesis of 1,2,3,4-tetrahydro-.beta.-carbolines from tryptamine-2-carboxylic acids
  作者：Krishnaswamy Narayanan、Liesl Schindler、James M. Cook

  DOI：10.1021/jo00001a066

  日期：1991.1

  The Pictet-Spengler condensation of various tryptamine-2-carboxylic acids 9a-f with carbonyl compounds in benzene/dioxane/trifluoroacetic acid (Table I) with simultaneous loss of carbon dioxide afforded directly the corresponding 1,2,3,4-tetrahydro-beta-carbolines 14a-j in good to excellent yields. This reaction greatly enhances the use of the Abramovitch-Shapiro method for the synthesis of highly oxygenated ring A substituted 1,2,3,4-tetrahydro-beta-carbolines (THBC). The lactams 14f,g and 14h are key intermediates for the synthesis of ring A substituted 1-methoxycanthin-6-one analogues.
• 881. Tryptamines, carbolines, and related compounds. Part III. 1-Methyl- and 1 : N-dimethyl-tryptamines
  作者：R. A. Abramovitch

  DOI：10.1039/jr9560004593

  日期：——