tetraethyl 2,2'-(2,5-bis(bromomethyl)-1-(phenylsulfonyl)-1H-pyrrole-3,4-diyl)bis(methan-1-ylidene)dimalonate | 129661-79-6

• 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: tetraethyl 2,2'-(2,5-bis(bromomethyl)-1-(phenylsulfonyl)-1H-pyrrole-3,4-diyl)bis(methan-1-ylidene)dimalonate
• 英文别名: tetraethyl <(1-phenylsulfonyl-2,5-dibromomethyl-3,4-pyrrolediyl)dimethylene>bis(propanedioate)
• CAS: 129661-79-6
• 化学式: C₂₈H₃₁Br₂NO₁₀S
• 分子量: 733.429
• InChiKey: GHYAFIPVKRIBKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  144.27
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  tetraethyl 2,2'-(2,5-bis(bromomethyl)-1-(phenylsulfonyl)-1H-pyrrole-3,4-diyl)bis(methan-1-ylidene)dimalonate 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以35%的产率得到4-phenylsulfonyl-4,6-dihydro-2H-dipyrrolo<3,4-b:3',4'-d>pyrrole
  参考文献：
  名称：

  Synthesis of 2,4-Dihydropyrrolo[3,4-b]pyrroles and 4,6-Dihydro-2H-dipyrrolo[3,4-b:3',4'-d]pyrroles

  摘要：

  DOI：

  10.3987/com-89-5237
• 作为产物：
  描述：

  tetraethyl <(2,5-dimethyl-3,4-pyrrolediyl)dimethylene>bis(propanedioate) 在 N-溴代丁二酰亚胺(NBS) 、 potassium hydride 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 2.5h， 生成 tetraethyl 2,2'-(2,5-bis(bromomethyl)-1-(phenylsulfonyl)-1H-pyrrole-3,4-diyl)bis(methan-1-ylidene)dimalonate
  参考文献：
  名称：

  Synthesis of 2,4-Dihydropyrrolo[3,4-b]pyrroles and 4,6-Dihydro-2H-dipyrrolo[3,4-b:3',4'-d]pyrroles

  摘要：

  DOI：

  10.3987/com-89-5237

文献信息

• A Versatile Synthesis of Annulated Carbazole Analogs Involving a Domino Reaction of Bromomethylindoles with Arenes/Heteroarenes
  作者：Vasudevan Dhayalan、J. Arul Clement、Radhakrishnan Jagan、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.200801018

  日期：2009.2

  A ZnBr2-mediated arylation of aryl/heteroaryl methyl bromides with arenes at 80 °C led to the formation of arylated products, which underwent subsequent 1,5-sigmatropic rearrangement followed by electrocyclization and aromatization with loss of a diethylmalonate unit to afford the corresponding annulated products. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  ZnBr2 介导的芳基/杂芳基甲基溴与芳烃在 80°C 的芳基化形成芳基化产物，随后进行 1,5-σ 重排，然后进行电环化和芳构化，失去丙二酸二乙酯单元，得到相应的环化产物。产品。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• A one pot synthesis of annulated carbazole analogs
  作者：Arasambattu K. Mohanakrishnan、Vasudevan Dhayalan、J. Arul Clement、Ramalingam Balamurugan Radhakrishn Sureshbabu、Natarajan Senthil Kumar

  DOI：10.1016/j.tetlet.2008.07.036

  日期：2008.10.6

  A ZnBr2-mediated arylation of N-protected 2/3-bromomethylindoles containing an electron-deficient malonylidene unit with arenes at 80 degrees C led to the formation of arylated products, which on Unprecedented 1,5-sigmatropic rearrangement followed by electrocyclization and subsequent aromatization with loss of diethylmalonate furnished the corresponding annulated carbazoles in reasonable yields. (C) 2008 Published by Elsevier Ltd.
• Donor–acceptor-Type Polymers Based on Dithieno[2,3-<i>b</i>;7,6-<i>b</i>]carbazole Unit for Photovoltaic Applications
  作者：Atsushi Kimoto、Yusuke Tajima

  DOI：10.1021/ol300709u

  日期：2012.5.4

  Dithieno[2,3-b;7,6-b]carbazole (TCZT), a type of heteropentacene with nitrogen and sulfur atoms, was synthesized with a focus on the unique reactivity of carbazole via double intramolecular Friedel-Crafts acylation. A donor-acceptor-type polymer (PTCZTBT) was also synthesized, and Its physicochemical properties are reported.