methyl 4-methyl-β-carboline-3-carboxylate | 78539-13-6

• 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: methyl 4-methyl-β-carboline-3-carboxylate
• 英文别名: 4-methyl-β-carbolin-3-carboxylic acid methyl ester；4-Methyl-9h-pyrido[3,4-b]indole-3-carboxylic acid methyl ester；methyl 4-methyl-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 78539-13-6
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: BSWGBPCMNJROKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-methyl-β-carboline-3-carboxylate 生成 4-methyl-β-carbolin-3-carboxylic acid n-propyl ester
  参考文献：
  名称：

  EDER, U.;NEEF, G.;HUTH, A.;RAHTZ, D.;SCHMIECHEN, R.

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲氧基-N-甲基-1H-吲哚-2-甲酰胺 在 lithium aluminium tetrahydride 、 molecular sieve 、 四氯化钛 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 13.67h， 生成 methyl 4-methyl-β-carboline-3-carboxylate
  参考文献：
  名称：

  A new efficient synthesis of ethyl β-carboline-3-carboxylate (β-CCE) and methyl 4-methyl-β-carboline-3-carboxylate (4-methyl-β-CCM) starting fr

  摘要：

  Ethyl beta-carboline-3-carboxylate (9) and methyl 4-methyl-beta-carboline-3-carboxylate (15) were prepared in high yields hy condensing indole-2-carboxaldehyde (5) (itself prepared by lithium aluminum hydride reduction of the Weinreb amide derived from indole-2-carboxylic acid) with ethyl 2-amino-3,3-diethoxypropionate (6) and methyl 2-amino-3,3-diethoxybutyrate (12), respectively, followed by reduction of the imine bonds formed with sodium cyanoborohydride and cyclization of the resulting amines (8 and 14, respectively) using titanium (IV) chloride.

  DOI：

  10.1016/s0040-4020(01)80649-9

文献信息

• .beta.-Carbolin-3-carboxylic acid derivatives
  申请人：A/S Ferrosan

  公开号：US04371536A1

  公开（公告）日：1983-02-01

  A .beta.-carbolin-3-carboxylic acid derivative of the formula ##STR1## has valuable pharmacological properties when administered to patients, e.g. humans as a drug, have been shown to possess interesting tranquilizing activity.

  当给予患者，例如人类作为药物时，具有有价值的药理特性的一种公式为##STR1##的β-咔啉-3-羧酸衍生物已被证明具有有趣的镇静活性。
• Beta-carbolin-3-carboxylic acid derivatives, pharmaceutical compositions containing them and their therapeutical use
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0030254A1

  公开（公告）日：1981-06-17

  β-Carbolin-3-carboxylic acid derivatives of the formula wherein X, R3, R4, R9 and RA have various significances. These compounds possess valuable pharmacological properties. In particular, they act on the central nervous system and are suitable for use in psychopharmaceutical preparations.

  式中β-咔啉-3-羧酸衍生物 其中 X、R3、R4、R9 和 RA 具有不同的含义。 这些化合物具有宝贵的药理特性。特别是，它们可作用于中枢神经系统，适用于精神药物制剂。
• US4371536A
  申请人：——

  公开号：US4371536A

  公开（公告）日：1983-02-01
• US5010077A
  申请人：——

  公开号：US5010077A

  公开（公告）日：1991-04-23
• A new efficient synthesis of ethyl β-carboline-3-carboxylate (β-CCE) and methyl 4-methyl-β-carboline-3-carboxylate (4-methyl-β-CCM) starting fr
  作者：Mouloud Dekhane、Robert H. Dodd

  DOI：10.1016/s0040-4020(01)80649-9

  日期：1994.1

  Ethyl beta-carboline-3-carboxylate (9) and methyl 4-methyl-beta-carboline-3-carboxylate (15) were prepared in high yields hy condensing indole-2-carboxaldehyde (5) (itself prepared by lithium aluminum hydride reduction of the Weinreb amide derived from indole-2-carboxylic acid) with ethyl 2-amino-3,3-diethoxypropionate (6) and methyl 2-amino-3,3-diethoxybutyrate (12), respectively, followed by reduction of the imine bonds formed with sodium cyanoborohydride and cyclization of the resulting amines (8 and 14, respectively) using titanium (IV) chloride.