(6aS,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline | 548-42-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: (6aS,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline
• CAS: 548-42-5
• 化学式: C₁₆H₁₈N₂
• 分子量: 238.332
• InChiKey: XJOOMMHNYOJWCZ-HIFRSBDPSA-N

物化性质

• 熔点：
  198-208℃ (decomposition) (ethyl ether )
• 比旋光度：
  D20 -155° (c = 0.9 in chloroform); D20 -182° (c = 0.5 in pyridine)
• 沸点：
  370.93°C (rough estimate)
• 密度：
  0.9597 (rough estimate)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  (4S,5R)-5-(2-methylprop-1-enyl)-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine 在 lithium aluminium tetrahydride 、 selenium(IV) oxide 、 potassium carbonate 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙腈 为溶剂， 生成 (6aS,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline
  参考文献：
  名称：

  Simple Total Syntheses of (-)-Ergot Alkaloids and Thier (+)-Enantiomers by a Common Synthesis Method Utilizing Optical Resolution

  摘要：

  The first and simple total syntheses of (-)-isochanoclavine-I ((-)-1b), (-)-agroclavine ((-)-3), (-)-agroclavine-I ((-)-4), and (-)-norchanoclavine-I ((-)-5C) and their (+)-enantiomers are achieved from indole-3-carboxaldehyde (8) by a common synthesis method utilizing optical resolution. Absolute configuration of (-)-agroclavine-I is determined to be 5R and 10S for the first time. Preparations of both enantiomers of chanoclavine-I (1c) are also included.

  DOI：

  10.3987/com-97-7821

文献信息

• Simple Total Syntheses of (-)-Ergot Alkaloids and Thier (+)-Enantiomers by a Common Synthesis Method Utilizing Optical Resolution
  作者：Masanori Somei、Kyoko Nakagawa

  DOI：10.3987/com-97-7821

  日期：——

  The first and simple total syntheses of (-)-isochanoclavine-I ((-)-1b), (-)-agroclavine ((-)-3), (-)-agroclavine-I ((-)-4), and (-)-norchanoclavine-I ((-)-5C) and their (+)-enantiomers are achieved from indole-3-carboxaldehyde (8) by a common synthesis method utilizing optical resolution. Absolute configuration of (-)-agroclavine-I is determined to be 5R and 10S for the first time. Preparations of both enantiomers of chanoclavine-I (1c) are also included.