11-Methoxy-4,5-(methylenedioxy)-8H-quino<4,3-b>carbazol-1(2H)-one | 164261-54-5

• 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: 11-Methoxy-4,5-(methylenedioxy)-8H-quino<4,3-b>carbazol-1(2H)-one
• 英文别名: 18-Methoxy-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(21),17,19,23-nonaen-12-one
• CAS: 164261-54-5
• 化学式: C₂₁H₁₄N₂O₄
• 分子量: 358.353
• InChiKey: IZJLWRLYTSTZOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11-Methoxy-4,5-(methylenedioxy)-8H-quino<4,3-b>carbazol-1(2H)-one 在 三氯氧磷 作用下， 反应 24.0h， 生成 12-chloro-18-methoxy-5,7-dioxa-11,22-diazahexacyclo[11.11.0.02,10.04,8.015,23.016,21]tetracosa-1(13),2,4(8),9,11,14,16(21),17,19,23-decaene
  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：

  22-(Benzenesulfonyl)-18-methoxy-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(21),17,19,23-nonaen-12-one 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 生成 11-Methoxy-4,5-(methylenedioxy)-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