2-ethyl-1-(3-fluorophenyl)-2,3,4,9-tetrahydro-1H-β-carboline | 141219-00-3

• 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: 2-ethyl-1-(3-fluorophenyl)-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: 2-Ethyl-1-(3-fluorophenyl)-2,3,4,9-tetrahydro-beta-carboline；2-ethyl-1-(3-fluorophenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole
• CAS: 141219-00-3
• 化学式: C₁₉H₁₉FN₂
• 分子量: 294.372
• InChiKey: UDTBAOGIUIVUQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethyl-1-(3-fluorophenyl)-2,3,4,9-tetrahydro-1H-β-carboline 、 丁炔二酸二甲酯 以 二氯甲烷 为溶剂， 反应 264.0h， 以27%的产率得到dimethyl 3-ethyl-6-(3-fluorophenyl)-2,3,6,7-tetrahydro-1H-azocino[5,4-b]indole-4,5-dicarboxylate
  参考文献：
  名称：

  Synthesis of 6-aryl-Substituted Azocino-[5,4-b]indoles from 1-aryl-Substituted 2-Ethyltetrahydro-β-Carbolines

  摘要：

  We optimized the reaction of tetrahydropyridine ring expansion in 1-aryl-substituted tetrahydro-beta-carbolines by the action of activated alkynes and achieved higher than 70% yields of the target indoloazocines. The substituents in the 1-aryl ring and at the indole nitrogen atom were shown to affect the rate and selectivity of this transformation.

  DOI：

  10.1007/s10593-014-1518-z
• 作为产物：
  描述：

  碘乙烷 、 1-(3-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 以75%的产率得到2-ethyl-1-(3-fluorophenyl)-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Synthesis of 6-aryl-Substituted Azocino-[5,4-b]indoles from 1-aryl-Substituted 2-Ethyltetrahydro-β-Carbolines

  摘要：

  We optimized the reaction of tetrahydropyridine ring expansion in 1-aryl-substituted tetrahydro-beta-carbolines by the action of activated alkynes and achieved higher than 70% yields of the target indoloazocines. The substituents in the 1-aryl ring and at the indole nitrogen atom were shown to affect the rate and selectivity of this transformation.

  DOI：

  10.1007/s10593-014-1518-z

文献信息

• Transformation of 2-ethyl-1-m-fluoro-phenyl-β-carboline by the action of dimethyl acetylenedicarboxylate in the presence of indoles. New method of synthesis of bisindolylarylmethanes
  作者：L. G. Voskressensky、L. N. Kulikova、A. S. Kasatochkina、A. V. Listratova、Flavien A. Toze、T. N. Borisova、A. V. Varlamov

  DOI：10.1007/s10593-010-0617-8

  日期：2010.12