6,8-dimethoxy-1,2,3,4-terahydro-β-carbolinone-1 | 94850-36-9

• 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: 6,8-dimethoxy-1,2,3,4-terahydro-β-carbolinone-1
• 英文别名: 6,8-Dimethoxy-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
• CAS: 94850-36-9
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: SQUSVCRGYDXUCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,8-dimethoxy-1,2,3,4-terahydro-β-carbolinone-1 在 氢氧化钾 作用下， 生成 5,7-dimethoxytryptamine-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
• 作为产物：
  描述：

  2,3-Piperidinedione 3-[(2,4-dimethoxyphenyl)hydrazone] 生成 6,8-dimethoxy-1,2,3,4-terahydro-β-carbolinone-1
  参考文献：
  名称：

  NARAYANAN, KRISHNASWAMY;SCHINDLER, LIESL;COOK, JAMES M., J. ORG. CHEM., 56,(1991) N, C. 359-365

  摘要：

  DOI：

文献信息

• Indole derivatives. 125. Synthesis of disubstitutep tryptamines
  作者：N. N. Suvorov、L. Kh. Vinograd、K. F. Turchin、G. N. Il'ina、M. M. Vigdorchik、T. Ya. Filipenko

  DOI：10.1007/bf00513577

  日期：1984.8
• 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.