(-)-4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole | 111614-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (-)-4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole
• 英文别名: (-)-4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenz(cd)indole；(4R,5R)-5-(2-methylprop-1-enyl)-4-nitro-1,3,4,5-tetrahydrobenzo[cd]indole
• CAS: 111614-01-8
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: JJGFJTLRHZOHTH-TZMCWYRMSA-N

物化性质

• 沸点：
  456.6±45.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 在 盐酸 、 叔丁基过氧化氢 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 selenium(IV) oxide 、 amalgamated zinc 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 裸麦角碱
  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
• 作为产物：
  描述：

  (4S,5R)-5-(2-methylprop-1-enyl)-4-nitro-1,3,4,5-tetrahydrobenzo[cd]indole 在 三乙胺 作用下， 以79%的产率得到(-)-4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole
  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

• Nakagawa, Kyoko; Somei, Masanori, Heterocycles, 1991, vol. 32, # 5, p. 873 - 878
  作者：Nakagawa, Kyoko、Somei, Masanori

  DOI：——

  日期：——
• ——
  作者：SOMEHI MASANORI

  DOI：——

  日期：——
• SOMEI, MASANORI;YAMADA, FUMIO;MAKITA, YOSHIHIKO, HETEROCYCLES, 26,(1987) N 1, 895-899
  作者：SOMEI, MASANORI、YAMADA, FUMIO、MAKITA, YOSHIHIKO

  DOI：——

  日期：——
• 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.