3-(β-Carbethoxyvinyl)-1-(phenylsulfonyl)-2-<β'-(6'-nitroveratryl)vinyl>indole

• 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: 3-(β-Carbethoxyvinyl)-1-(phenylsulfonyl)-2-<β'-(6'-nitroveratryl)vinyl>indole
• 英文别名: ethyl (E)-3-[1-(benzenesulfonyl)-2-[(E)-2-(4,5-dimethoxy-2-nitrophenyl)ethenyl]indol-3-yl]prop-2-enoate
• 化学式: C₂₉H₂₆N₂O₈S
• 分子量: 562.6
• InChiKey: RXTCCBAPHZLPES-YXLFCKQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(β-Carbethoxyvinyl)-1-(phenylsulfonyl)-2-<β'-(6'-nitroveratryl)vinyl>indole 在 palladium on activated charcoal 作用下， 以 xylene 为溶剂， 反应 24.0h， 以91%的产率得到3-Carbethoxy-9-(phenylsulfonyl)-2-(6'-nitroveratryl)carbazole
  参考文献：
  名称：

  A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder

  摘要：

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.

  DOI：

  10.1021/jo00112a011
• 作为产物：
  描述：

  2-甲基吲哚-3-甲醛 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 、 乙二醇二甲醚 为溶剂， 反应 20.0h， 生成 3-(β-Carbethoxyvinyl)-1-(phenylsulfonyl)-2-<β'-(6'-nitroveratryl)vinyl>indole
  参考文献：
  名称：

  A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder

  摘要：

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.

  DOI：

  10.1021/jo00112a011

文献信息

• A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder
  作者：Arasambattu K. Mohanakrishnan、Panayencheri C. Srinivasan

  DOI：10.1021/jo00112a011

  日期：1995.4

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.