(E)-4,5-trans-5-(2-hydroxymethyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole | 106488-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-4,5-trans-5-(2-hydroxymethyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole
• 英文别名: (E)-4,5-trans-5-(2-hydroxymethyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenz[cd]indole；(E)-2-methyl-3-[(4S,5S)-4-nitro-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol
• CAS: 106488-71-5；106566-45-4；106566-46-5；109216-12-8；109216-13-9；109216-14-0
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: BTWNBZAQUWJLDN-HDPQFUGUSA-N

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)-4,5-trans-5-(2-hydroxymethyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 在 盐酸 、 sodium hypochlorite 、 2-甲基-2-丁烯 、 三乙胺 、 pyridinium chlorochromate 、 汞 、 锌 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  The First Total Synthesis of (±)-Chanoclavine-I Acid and an Alternative Total Synthesis of (±)-Chanoclavine-I

  摘要：

  The total synthesis of (+/-)-chanoclavine-I acid was achieved for the first time. An alternative total synthesis of (+/-)-chanoclavine-I was also reported.

  DOI：

  10.3987/com-90-5577
• 作为产物：
  描述：

  (E)-4,5-trans-5-(2-formyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenz[cd]indole 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以93%的产率得到(E)-4,5-trans-5-(2-hydroxymethyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole
  参考文献：
  名称：

  Yamada, Fumio; Makita, Yoshihiko; Somei, Masanori, Heterocycles, 2007, vol. 72, p. 599 - 620

  摘要：

  DOI：

文献信息

• Somei, Masanori; Makita, Yoshihiko; Yamada, Fumio, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 2, p. 948 - 950
  作者：Somei, Masanori、Makita, Yoshihiko、Yamada, Fumio

  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.
• Yamada, Fumio; Makita, Yoshihiko; Somei, Masanori, Heterocycles, 2007, vol. 72, p. 599 - 620
  作者：Yamada, Fumio、Makita, Yoshihiko、Somei, Masanori

  DOI：——

  日期：——
• The First Total Synthesis of (±)-Chanoclavine-I Acid and an Alternative Total Synthesis of (±)-Chanoclavine-I
  作者：Masanori Somei、Harunobu Mukaiyama、Yoko Nomura、Kyoko Nakagawa

  DOI：10.3987/com-90-5577

  日期：——

  The total synthesis of (+/-)-chanoclavine-I acid was achieved for the first time. An alternative total synthesis of (+/-)-chanoclavine-I was also reported.