3-Carbethoxy-9-(phenylsulfonyl)-2-<3',4'-(methylenedioxy)-6'-nitrophenyl>carbazole | 164261-45-4

• 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: 3-Carbethoxy-9-(phenylsulfonyl)-2-<3',4'-(methylenedioxy)-6'-nitrophenyl>carbazole
• 英文别名: Ethyl 9-(benzenesulfonyl)-2-(6-nitro-1,3-benzodioxol-5-yl)carbazole-3-carboxylate
• CAS: 164261-45-4
• 化学式: C₂₈H₂₀N₂O₈S
• 分子量: 544.541
• InChiKey: DTDIOXKTZVWGLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 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-Carbethoxy-9-(phenylsulfonyl)-2-<3',4'-(methylenedioxy)-6'-nitrophenyl>carbazole 在 W₂ grade Ra-Ni 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 22-(Benzenesulfonyl)-5,7-dioxa-11,22-diazahexacyclo[11.11.0.02,10.04,8.015,23.016,21]tetracosa-1(13),2,4(8),9,14,16,18,20,23-nonaen-12-one
  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：

  3-(β-Carbethoxyvinyl)-1-(phenylsulfonyl)-2-<β'-<3',4'-(methylenedioxy)-6'-nitrophenyl>vinyl>indole 在 palladium on activated charcoal 作用下， 以 xylene 为溶剂， 反应 24.0h， 以88%的产率得到3-Carbethoxy-9-(phenylsulfonyl)-2-<3',4'-(methylenedioxy)-6'-nitrophenyl>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