1-methyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline | 16498-67-2

• 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-methyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: (+/-)-9-methyleleagnine；1,9-dimethyl-2,3,4,9-tetrahydro-1H-β-carboline；1,9-Dimethyl-1,2,3,4-tetrahydro-β-carbolin；9-Methyl-1,2,3,4-tetrahydroharman；1,9-dimethyl-2,3,4,9-tetrahydro-1H-beta-carboline；1,9-dimethyl-1,2,3,4-tetrahydropyrido[3,4-b]indole
• CAS: 16498-67-2
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: GDGWNEFBBLUBMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  17
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,2,3,4-四氢-9H-吡啶[3,4-B]并吲哚 在 正丁基锂 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 mineral oil 为溶剂， 反应 33.63h， 生成 1-methyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Preparation of 1-Substituted Tetrahydro-β-carbolines by Lithiation–Substitution

  摘要：

  A method to prepare 1-substituted N-Boc-tetrahydro-beta-carbolines was developed by lithiation followed by electrophilic substitution. The deprotonation to give the organolithium was optimized by in situ IR spectroscopy and showed that the Bot group rotates slowly at low temperature. The chemistry was applied to the synthesis of 9-methyleleagnine (N-methyltetrahydroharman) and 11-methylharmicine.

  DOI：

  10.1021/acs.joc.5b00725

文献信息

• Preparation of 1-Substituted Tetrahydro-β-carbolines by Lithiation–Substitution
  作者：Edward J. Cochrane、Lorraine A. Hassall、Iain Coldham

  DOI：10.1021/acs.joc.5b00725

  日期：2015.6.5

  A method to prepare 1-substituted N-Boc-tetrahydro-beta-carbolines was developed by lithiation followed by electrophilic substitution. The deprotonation to give the organolithium was optimized by in situ IR spectroscopy and showed that the Bot group rotates slowly at low temperature. The chemistry was applied to the synthesis of 9-methyleleagnine (N-methyltetrahydroharman) and 11-methylharmicine.