5-methoxyindol-2-yl 3-carboxy-4-pyridyl ketone | 143706-88-1

• 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: 5-methoxyindol-2-yl 3-carboxy-4-pyridyl ketone
• 英文别名: 4-(5-methoxy-1H-indole-2-carbonyl)pyridine-3-carboxylic acid
• CAS: 143706-88-1
• 化学式: C₁₆H₁₂N₂O₄
• 分子量: 296.282
• InChiKey: CINICWPIBNHBCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  619.1±55.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  92.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methoxyindol-2-yl 3-carboxy-4-pyridyl ketone 在 乙酸酐 作用下， 反应 26.0h， 生成 8-methoxyindolo<1,2-b><2,7>naphthyridine-5,12-quinone
  参考文献：
  名称：

  A versatile and efficient construction of the 6H-pyrido[4,3-b]carbazole ring system. Syntheses of the antitumor alkaloids ellipticine, 9-methoxyellipticine, and olivacine, and their analogs

  摘要：

  A general and efficient synthesis of the 6H-pyrido[4,3-b]carbazole ring system is described, in which the key steps are (1) regioselective acylation of a 2-lithio-1-(phenylsulfonyl)indole (14) with 3,4-pyridinedicarboxylic acid anhydride (10), (2) cyclization of the deprotected keto acid 17 to keto lactam 19 with acetic anhydride, and (3) the addition of methyllithium to give, after reduction of the intermediate diol 23 with sodium borohydride, the target ring system. In this fashion, ellipticine (1a), 9-methoxyellipticine (1b), and 9-hydroxyellipticine (1c) were synthesized in excellent overall yields from indole. The use of Superhydride, in place of 1 equiv of methyllithium, provided a synthesis of olivacine (2), and the use of phthalic anhydride in the sequence allowed for the preparation of 6,11-dimethylbenzo[b]carbazole (48). The overall yields of ellipticine (1a) (54%) and 9-methoxyellipticine (1b) (47%) in six steps from their respective indoles represent one of the most efficient syntheses of these antitumor alkaloids.

  DOI：

  10.1021/jo00048a022
• 作为产物：
  描述：

  4-硝基间甲苯酚 在 palladium on activated charcoal 正丁基锂 、 氢气 、 sodium methylate 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， -100.0~25.0 ℃ 、303.98 kPa 条件下， 反应 59.0h， 生成 5-methoxyindol-2-yl 3-carboxy-4-pyridyl ketone
  参考文献：
  名称：

  A versatile and efficient construction of the 6H-pyrido[4,3-b]carbazole ring system. Syntheses of the antitumor alkaloids ellipticine, 9-methoxyellipticine, and olivacine, and their analogs

  摘要：

  A general and efficient synthesis of the 6H-pyrido[4,3-b]carbazole ring system is described, in which the key steps are (1) regioselective acylation of a 2-lithio-1-(phenylsulfonyl)indole (14) with 3,4-pyridinedicarboxylic acid anhydride (10), (2) cyclization of the deprotected keto acid 17 to keto lactam 19 with acetic anhydride, and (3) the addition of methyllithium to give, after reduction of the intermediate diol 23 with sodium borohydride, the target ring system. In this fashion, ellipticine (1a), 9-methoxyellipticine (1b), and 9-hydroxyellipticine (1c) were synthesized in excellent overall yields from indole. The use of Superhydride, in place of 1 equiv of methyllithium, provided a synthesis of olivacine (2), and the use of phthalic anhydride in the sequence allowed for the preparation of 6,11-dimethylbenzo[b]carbazole (48). The overall yields of ellipticine (1a) (54%) and 9-methoxyellipticine (1b) (47%) in six steps from their respective indoles represent one of the most efficient syntheses of these antitumor alkaloids.

  DOI：

  10.1021/jo00048a022

文献信息

• A versatile and efficient construction of the 6H-pyrido[4,3-b]carbazole ring system. Syntheses of the antitumor alkaloids ellipticine, 9-methoxyellipticine, and olivacine, and their analogs
  作者：Gordon W. Gribble、Mark G. Saulnier、Judy A. Obaza-Nutaitis、Daniel M. Ketcha

  DOI：10.1021/jo00048a022

  日期：1992.10

  A general and efficient synthesis of the 6H-pyrido[4,3-b]carbazole ring system is described, in which the key steps are (1) regioselective acylation of a 2-lithio-1-(phenylsulfonyl)indole (14) with 3,4-pyridinedicarboxylic acid anhydride (10), (2) cyclization of the deprotected keto acid 17 to keto lactam 19 with acetic anhydride, and (3) the addition of methyllithium to give, after reduction of the intermediate diol 23 with sodium borohydride, the target ring system. In this fashion, ellipticine (1a), 9-methoxyellipticine (1b), and 9-hydroxyellipticine (1c) were synthesized in excellent overall yields from indole. The use of Superhydride, in place of 1 equiv of methyllithium, provided a synthesis of olivacine (2), and the use of phthalic anhydride in the sequence allowed for the preparation of 6,11-dimethylbenzo[b]carbazole (48). The overall yields of ellipticine (1a) (54%) and 9-methoxyellipticine (1b) (47%) in six steps from their respective indoles represent one of the most efficient syntheses of these antitumor alkaloids.