(E,E)-2-(cyclohex-1-enyl)-4-nitro-3-(4-phenylbuta-1,3-dienyl)pyrrole | 180282-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E,E)-2-(cyclohex-1-enyl)-4-nitro-3-(4-phenylbuta-1,3-dienyl)pyrrole
• 英文别名: 2-(cyclohexen-1-yl)-4-nitro-3-[(1E,3E)-4-phenylbuta-1,3-dienyl]-1H-pyrrole
• CAS: 180282-22-8
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: AOIVSPXHXZYLIQ-HPIZBCMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (E,E)-2-(cyclohex-1-enyl)-4-nitro-3-(4-phenylbuta-1,3-dienyl)pyrrole 以 various solvent(s) 为溶剂， 反应 2.0h， 以78%的产率得到rac-4-nitro-((1R,6S,8S)-6-phenyl-5,8-tetramethylenetricyclo[3.2.1.0^2,7]oct-3-eno)[4,3-b]pyrrole
  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
• 作为产物：
  描述：

  1-nitro-6-phenylhexa-1,3,5-triene 、 (isocyanotosylmethylidene)cyclohexane 在 potassium tert-butylate 作用下， 生成 (E,E)-2-(cyclohex-1-enyl)-4-nitro-3-(4-phenylbuta-1,3-dienyl)pyrrole
  参考文献：
  名称：

  An Efficient Synthesis of Substituted 3(4)-Nitropyrroles from Nitroalkenes and Tosylmethyl Isocyanides

  摘要：

  通过甲苯磺酰甲基异氰化物 (TosMIC) 或不饱和同系物的碱诱导加成，可在一次操作中有效合成一系列 2-位和 3-位（或仅 3-位）具有烯基取代基的 3(4)-硝基吡咯。 TosMIC，硝基烯烃。

  DOI：

  10.1055/s-1996-4306

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。
• An Efficient Synthesis of Substituted 3(4)-Nitropyrroles from Nitroalkenes and Tosylmethyl Isocyanides
  作者：Ronald ten Have、Frederik R. Leusink、Albert M. van Leusen

  DOI：10.1055/s-1996-4306

  日期：1996.7

  A series of 3(4)-nitropyrroles with alkenyl substituents in the 2- and 3-positions (or 3-position only) is synthesized efficiently in one operation by a base-induced addition of tosylmethyl isocyanide (TosMIC), or unsaturated homologs of TosMIC, to nitroalkenes.

  通过甲苯磺酰甲基异氰化物 (TosMIC) 或不饱和同系物的碱诱导加成，可在一次操作中有效合成一系列 2-位和 3-位（或仅 3-位）具有烯基取代基的 3(4)-硝基吡咯。 TosMIC，硝基烯烃。
• A novel synthesis of 3-nitroindoles via electrocyclization of 2,3-(dialk-1-enyl)-4-nitropyrroles
  作者：Ronald ten Have、Albert M van Leusen

  DOI：10.1016/s0040-4020(97)10405-7

  日期：1998.2

  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.