(E,E)-1-methyl-4-nitro-3-(4-phenylethenyl)-2-(1-phenylprop-1-enyl)pyrrole | 180282-19-3

• 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)-1-methyl-4-nitro-3-(4-phenylethenyl)-2-(1-phenylprop-1-enyl)pyrrole
• 英文别名: 1-methyl-4-nitro-3-[(E)-2-phenylethenyl]-2-[(E)-1-phenylprop-1-enyl]pyrrole
• CAS: 180282-19-3
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: JBUGWYIXKWKBFP-GAFTYJJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E,E)-1-methyl-4-nitro-3-(4-phenylethenyl)-2-(1-phenylprop-1-enyl)pyrrole 以 硝基苯 为溶剂， 反应 5.0h， 以85%的产率得到1,6-dimethyl-5,7-diphenyl-3-nitroindole
  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-4-phenylbutadiene 在 氢氧化钾 、 potassium tert-butylate 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成 (E,E)-1-methyl-4-nitro-3-(4-phenylethenyl)-2-(1-phenylprop-1-enyl)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

• 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.