12-chloro-5,7-dioxa-11,16-diazahexacyclo[11.11.0.02,10.04,8.015,23.017,22]tetracosa-1(13),2,4(8),9,11,14,17,19,21,23-decaene | 1027168-93-9

• 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-chloro-5,7-dioxa-11,16-diazahexacyclo[11.11.0.02,10.04,8.015,23.017,22]tetracosa-1(13),2,4(8),9,11,14,17,19,21,23-decaene
• CAS: 1027168-93-9
• 化学式: C₂₀H₁₁ClN₂O₂
• 分子量: 346.773
• InChiKey: LMUXXSGZLPNLDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二甲基-1,3-二氨基丙烷 、 12-chloro-5,7-dioxa-11,16-diazahexacyclo[11.11.0.02,10.04,8.015,23.017,22]tetracosa-1(13),2,4(8),9,11,14,17,19,21,23-decaene 反应 20.0h， 生成 1-<3'-(N,N-Dimethylamino)propyl>-4,5-(methylenedioxy)-12H-quino<3,4-b>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-Carbethoxy-9-(phenylsulfonyl)-3-<3',4'-(methylenedioxy)-6'-nitrophenyl>carbazole 在 sodium hydroxide 、 W₂ grade Ra-Ni 、 三氯氧磷 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 12-chloro-5,7-dioxa-11,16-diazahexacyclo[11.11.0.02,10.04,8.015,23.017,22]tetracosa-1(13),2,4(8),9,11,14,17,19,21,23-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