(+)-4,5-cis-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole | 79133-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+)-4,5-cis-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole
• 英文别名: (4R,5S)-5-(2-methylprop-1-enyl)-4-nitro-1,3,4,5-tetrahydrobenzo[cd]indole
• CAS: 79133-62-3；79133-63-4；111614-01-8；113532-93-7；113532-94-8；135968-42-2；135968-43-3；135968-44-4
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: JJGFJTLRHZOHTH-GXTWGEPZSA-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-cis-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenz-indole
  参考文献：
  名称：

  从4-oxo-4,5,6,7-四氢吲哚轻松合成4-（磺酰基甲基）吲哚：6,7-secoagroclavine的正式全合成

  摘要：

  开发了一种由4-氧代-4,5,6,7-四氢吲哚合成4-（磺酰基甲基）吲哚的简便方法，并完成了6,7-仲豆蔻的正式全合成以证明该砜的多功能性。

  DOI：

  10.1016/s0040-4039(00)84745-0
• 作为产物：
  描述：

  4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenz-indole 在 sodium methylate 、 溶剂黄146 作用下， 生成 (+)-4,5-cis-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole
  参考文献：
  名称：

  Total Syntheses of (±)-Agroclavine-I, (±)-6-Nor-chanoclavine-II, and (±)-Chanoclavine-II

  摘要：

  DOI：

  10.3987/r-1987-04-0895

文献信息

• A facile synthesis of 4-(sulfonylmethyl)indoles from 4-oxo-4,5,6,7-tetrahydroindole: Formal total synthesis of 6,7-secoagroclavine
  作者：Naoto Hatanaka、Osamu Ozaki、Masakatsu Matsumoto

  DOI：10.1016/s0040-4039(00)84745-0

  日期：——

  A facile and short procedure for 4-(sulfonylmethyl)indole synthesis from 4-oxo-4,5,6,7-tetrahydroindole is developed and formal total synthesis of 6,7-secoagroclavine is completed to prove the versatility of this sulfone.

  开发了一种由4-氧代-4,5,6,7-四氢吲哚合成4-（磺酰基甲基）吲哚的简便方法，并完成了6,7-仲豆蔻的正式全合成以证明该砜的多功能性。
• TOTAL SYNTHESIS OF ERGOT ALKALOID, (±)-6,7-SECOAGROCLAVINE
  作者：Masanori Somei、Fumio Yamada、Yoshio Karasawa、Chikara Kaneko

  DOI：10.1246/cl.1981.615

  日期：1981.5.5

  Ergot alkaloid, (±)-6,7-secoagroclavine was synthesized from 2-methyl-5-nitroisoquinolinium iodide by three routes. In the course of the study, a novel intra-molecular γ-alkylation of allyl alcohol was found. Reaction of Grignard reagents with nitroalkanes to afford N-alkyl hydroxylamines was effectively used in the present synthesis.

  麦角生物碱 (±)-6,7-secoagroclavine 由 2-methyl-5-nitroisoquinolinium iodide 通过三种途径合成。在研究过程中，发现了烯丙醇的新型分子内γ-烷基化。格氏试剂与硝基烷烃反应得到 N-烷基羟胺被有效地用于本合成。
• Total Syntheses of (±)-Agroclavine-I, (±)-6-Nor-chanoclavine-II, and (±)-Chanoclavine-II
  作者：Masanori Somei、Fumio Yamada、Yoshihiko Makita

  DOI：10.3987/r-1987-04-0895

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

  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.