(E)-2-methyl-3-[(4R,5R)-4-nitro-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol | 194346-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2-methyl-3-[(4R,5R)-4-nitro-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol
• CAS: 194346-18-4
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: BTWNBZAQUWJLDN-DHTPOUDLSA-N

物化性质

• 沸点：
  523.7±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-3-[(4R,5R)-4-nitro-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol 在 盐酸 、 amalgamated zinc 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 [(4R,5R)-5-((E)-3-Hydroxy-2-methyl-propenyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid methyl ester
  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 叔丁基过氧化氢 、 sodium tetrahydroborate 、 selenium(IV) oxide 、 三乙胺 作用下， 反应 2.0h， 生成 (E)-2-methyl-3-[(4R,5R)-4-nitro-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol
  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