(E)-1-methyl-3-nitro-5-(2-phenylethenyl)-6,7,8,9-tetrahydrobenz[g]indole | 144882-40-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-methyl-3-nitro-5-(2-phenylethenyl)-6,7,8,9-tetrahydrobenz[g]indole
• 英文别名: 1-methyl-3-nitro-5-[(E)-2-phenylethenyl]-6,7,8,9-tetrahydrobenzo[g]indole
• CAS: 144882-40-6
• 化学式: C₂₁H₂₀N₂O₂
• 分子量: 332.402
• InChiKey: VZERIGIMVZYYPY-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E,E)-2-(cyclohex-1-enyl)-1-methyl-4-nitro-3-(4-phenylbuta-1,3-dienyl)pyrrole 以 various solvent(s) 为溶剂， 反应 2.0h， 以1%的产率得到(E)-1-methyl-3-nitro-5-(2-phenylethenyl)-6,7,8,9-tetrahydrobenz[g]indole
  参考文献：
  名称：

  A novel synthesis of 3-nitroindoles via electrocyclization of 2,3-(dialk-1-enyl)-4-nitropyrroles

  摘要：

  3-Nitroindoles (10) are prepared in good yields via a thermal 6 pi-electrocyclization of 2,3-(dialkenyl)-4-nitropyrroles (4) in nitrobenzene, a solvent which causes in situ aromatization of the initially formed dihydroindoles (8). The corresponding reaction of 2-alkenyl-3-alkadienyl-4-nitropyrroles (5) also leads to 3-nitroindoles (11), however, now together with 3-nitrotetrahydroindole derivatives (12). The latter compounds are formed by a tandem 6 pi-electrocyclization - intramolecular Diels-Alder reaction, and are the predominant (or only) products when nitrobenzene is replaced by triglyme. (C) 1997, Elsevier Science Ltd. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10405-7

文献信息

• Generation of 2,3-dimethylene-2,3-dihydropyrrole derivatives; intermediates in intra- and inter-molecular Diels–Alder reactions
  作者：Frederik R. Leusink、Ronald ten Have、Kiempe J. van den Berg、Albert M. van Leusen

  DOI：10.1039/c39920001401

  日期：——

  Three different approaches are described for the generation of derivatives of 2,3-dimethylene-2,3-dihydropyrrole 2, which are reactive intermediates in Diels–Alder cycloaddition reactions; one of the intramolecular cycloadditions provides a new tricyclo[3.2.1.02,7]octane compound 8.

  本文介绍了生成 2,3-二亚甲基-2,3-二氢吡咯 2 衍生物的三种不同方法，这些衍生物是 DielsâAlder 环加成反应中的活性中间体；其中一种分子内环加成反应提供了一种新的三环[3.2.1.02,7]辛烷化合物 8。