N-octyl-2,7-bis(4,4,5,5-tetramethyl-1,3-dioxa-2-borolan-2-yl)-1,8-dimethylcarbazole | 755758-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-octyl-2,7-bis(4,4,5,5-tetramethyl-1,3-dioxa-2-borolan-2-yl)-1,8-dimethylcarbazole
• 英文别名: 1,8-Dimethyl-9-octyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole
• CAS: 755758-80-6
• 化学式: C₃₄H₅₁B₂NO₄
• 分子量: 559.405
• InChiKey: QJGYXFIYYFGTNE-UHFFFAOYSA-N

物化性质

• 熔点：
  168-170 °C
• 沸点：
  633.7±55.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.37
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  41.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-octyl-2,7-bis(4,4,5,5-tetramethyl-1,3-dioxa-2-borolan-2-yl)-1,8-dimethylcarbazole 、 1-溴-2-硝基苯 在 palladium diacetate potassium carbonate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以73%的产率得到N-octyl-2,7-bis(2'-nitrophenyl)-1,8-dimethylcarbazole
  参考文献：
  名称：

  Synthesis of Diindolocarbazoles by Cadogan Reaction:  Route to Ladder Oligo(p-aniline)s

  摘要：

  Symmetric and nonsymmetric diindolocarbazoles were successfully synthesized for the first time by a Cadogan ring closure using N-alkyl-2,7-disubstituted carbazole precursors. Cyclization reaction on N-alkyl-2,7-di(2'-nitrophenyl) carbazole derivatives is not regioselective and produced a separable mixture of symmetric and nonsymmetric diindolocarbazoles. A carbazole derivative with methyl protective groups at the 1- and 8-positions was therefore used to obtain a symmetric ladder oligo-(p-aniline) (compound 22). Optical and electrochemical properties of compound 22 indicate that its neutral semiconducting form is stable in air. This novel class of electroactive ladder oligomers should create new opportunities in micro- and nanoelectronics.

  DOI：

  10.1021/jo049419o
• 作为产物：
  描述：

  N-octyl-2,7-dihydroxy-1,8-dimethylcarbazole 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 4-二甲氨基吡啶 、 三乙胺 作用下， 以 吡啶 、 1,2-二氯乙烷 为溶剂， 反应 29.0h， 生成 N-octyl-2,7-bis(4,4,5,5-tetramethyl-1,3-dioxa-2-borolan-2-yl)-1,8-dimethylcarbazole
  参考文献：
  名称：

  Synthesis of Diindolocarbazoles by Cadogan Reaction:  Route to Ladder Oligo(p-aniline)s

  摘要：

  Symmetric and nonsymmetric diindolocarbazoles were successfully synthesized for the first time by a Cadogan ring closure using N-alkyl-2,7-disubstituted carbazole precursors. Cyclization reaction on N-alkyl-2,7-di(2'-nitrophenyl) carbazole derivatives is not regioselective and produced a separable mixture of symmetric and nonsymmetric diindolocarbazoles. A carbazole derivative with methyl protective groups at the 1- and 8-positions was therefore used to obtain a symmetric ladder oligo-(p-aniline) (compound 22). Optical and electrochemical properties of compound 22 indicate that its neutral semiconducting form is stable in air. This novel class of electroactive ladder oligomers should create new opportunities in micro- and nanoelectronics.

  DOI：

  10.1021/jo049419o

文献信息

• Synthesis of Diindolocarbazoles by Cadogan Reaction:  Route to Ladder Oligo(<i>p</i>-aniline)s
  作者：Jimmy Bouchard、Salem Wakim、Mario Leclerc

  DOI：10.1021/jo049419o

  日期：2004.8.1

  Symmetric and nonsymmetric diindolocarbazoles were successfully synthesized for the first time by a Cadogan ring closure using N-alkyl-2,7-disubstituted carbazole precursors. Cyclization reaction on N-alkyl-2,7-di(2'-nitrophenyl) carbazole derivatives is not regioselective and produced a separable mixture of symmetric and nonsymmetric diindolocarbazoles. A carbazole derivative with methyl protective groups at the 1- and 8-positions was therefore used to obtain a symmetric ladder oligo-(p-aniline) (compound 22). Optical and electrochemical properties of compound 22 indicate that its neutral semiconducting form is stable in air. This novel class of electroactive ladder oligomers should create new opportunities in micro- and nanoelectronics.