12-Benzenesulfonyl-5,12-dihydro-5,12-diaza-indeno[1,2-b]phenanthren-6-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 12-Benzenesulfonyl-5,12-dihydro-5,12-diaza-indeno[1,2-b]phenanthren-6-one
• 英文别名: 10-(Benzenesulfonyl)-10,20-diazapentacyclo[11.8.0.03,11.04,9.014,19]henicosa-1(13),2,4,6,8,11,14,16,18-nonaen-21-one
• 化学式: C₂₅H₁₆N₂O₃S
• 分子量: 424.48
• InChiKey: UDVOLICLYIZZLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12-Benzenesulfonyl-5,12-dihydro-5,12-diaza-indeno[1,2-b]phenanthren-6-one 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 生成 8H-Quino<4,3-b>carbazol-1(2H)-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-Carbethoxy-9-(phenylsulfonyl)-2-(2'-nitrophenyl)carbazole 在 W₂ grade Ra-Ni 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 12-Benzenesulfonyl-5,12-dihydro-5,12-diaza-indeno[1,2-b]phenanthren-6-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