4,8-diamino-1,5-dibutoxy-3,7-bis(trimethylsilylethynyl)-naphthalene | 668448-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,8-diamino-1,5-dibutoxy-3,7-bis(trimethylsilylethynyl)-naphthalene
• 英文别名: 4,8-Dibutoxy-2,6-bis(2-trimethylsilylethynyl)naphthalene-1,5-diamine
• CAS: 668448-72-4
• 化学式: C₂₈H₄₂N₂O₂Si₂
• 分子量: 494.825
• InChiKey: OJFNRDRNGPTKMR-UHFFFAOYSA-N

物化性质

• 沸点：
  588.7±50.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,8-diamino-1,5-dibutoxy-3,7-bis(trimethylsilylethynyl)-naphthalene 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以83%的产率得到5,10-dibutoxy-indolo<7,6-g>indole
  参考文献：
  名称：

  New route to the synthesis of the indolo[7,6-g]indole (“bis(pyrrolo)naphthalene”) system starting from 1,5-dihydroxynaphthalene

  摘要：

  A short and convenient route for the synthesis of indolo[7,6-g]indole derivatives starting from dihydroxynaphthalene is described. 1,9-Dihydroxynaphthalene (I) after alkylation, nitration and reduction gave 4,8-diamino-1,5-dibutoxynaphthalene (4). After reaction with iodine, 4,8-diamino-1,5-disubstituted naphthalene gave the corresponding 3,7-diodonaphthalene (5) in nearly quantitative yields. Palladium-catalyzed reaction of this diiodonaphthalene derivative with (trimethylsilyl)acetylene (TMSA), followed by efficient CuI-mediated cyclization with simultaneous elimination of the TMS substituent, allowed an efficient preparation of 5,10-dibutoxyindolo[7,6-g]indole (8). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00121-5
• 作为产物：
  描述：

  1,5-二羟基萘 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 tin 、 copper(l) iodide 、 硫酸 、 碘 、 硝酸 作用下， 以 乙醇 、 溶剂黄146 、 三乙胺 为溶剂， 反应 6.0h， 生成 4,8-diamino-1,5-dibutoxy-3,7-bis(trimethylsilylethynyl)-naphthalene
  参考文献：
  名称：

  New route to the synthesis of the indolo[7,6-g]indole (“bis(pyrrolo)naphthalene”) system starting from 1,5-dihydroxynaphthalene

  摘要：

  A short and convenient route for the synthesis of indolo[7,6-g]indole derivatives starting from dihydroxynaphthalene is described. 1,9-Dihydroxynaphthalene (I) after alkylation, nitration and reduction gave 4,8-diamino-1,5-dibutoxynaphthalene (4). After reaction with iodine, 4,8-diamino-1,5-disubstituted naphthalene gave the corresponding 3,7-diodonaphthalene (5) in nearly quantitative yields. Palladium-catalyzed reaction of this diiodonaphthalene derivative with (trimethylsilyl)acetylene (TMSA), followed by efficient CuI-mediated cyclization with simultaneous elimination of the TMS substituent, allowed an efficient preparation of 5,10-dibutoxyindolo[7,6-g]indole (8). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00121-5

文献信息

• New route to the synthesis of the indolo[7,6-g]indole (“bis(pyrrolo)naphthalene”) system starting from 1,5-dihydroxynaphthalene
  作者：Jadwiga Sołoducho

  DOI：10.1016/s0040-4039(99)00121-5

  日期：1999.3

  A short and convenient route for the synthesis of indolo[7,6-g]indole derivatives starting from dihydroxynaphthalene is described. 1,9-Dihydroxynaphthalene (I) after alkylation, nitration and reduction gave 4,8-diamino-1,5-dibutoxynaphthalene (4). After reaction with iodine, 4,8-diamino-1,5-disubstituted naphthalene gave the corresponding 3,7-diodonaphthalene (5) in nearly quantitative yields. Palladium-catalyzed reaction of this diiodonaphthalene derivative with (trimethylsilyl)acetylene (TMSA), followed by efficient CuI-mediated cyclization with simultaneous elimination of the TMS substituent, allowed an efficient preparation of 5,10-dibutoxyindolo[7,6-g]indole (8). (C) 1999 Elsevier Science Ltd. All rights reserved.