1,2,3,4-tetrahydro-1-oxoacridine-9-carboxylic acid | 937644-37-6

• 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: 1,2,3,4-tetrahydro-1-oxoacridine-9-carboxylic acid
• 英文别名: 1-oxo-1,2,3,4-tetrahydroacridine-9-carboxylic acid；1-oxo-3,4-dihydro-2H-acridine-9-carboxylic acid
• CAS: 937644-37-6
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: WMRFUGBQHVSPTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-1-oxoacridine-9-carboxylic acid 、 胺苄醯甲酸 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以78%的产率得到6,7-dihydrodibenzo[b,j][1,7]phenanthroline-8,14-dicarboxylic acid
  参考文献：
  名称：

  Synthesis of 6,7-Dihydrodibenzo[b,j]phenanthroline Derivatives by Pfitzinger Condensation of Isatin and Cyclic Diketones

  摘要：

  All two kinds of 6,7-dihydrodibenzo[b,j]phenanthroline derivatives were synthesized by Pfitzinger condensation of isatins with 1,3-cyclohexanedione and 1,4-cyclohexanedione respectively. Structures of the derivatives were confirmed by NMR and other spectra data.

  DOI：

  10.3987/com-13-12894
• 作为产物：
  描述：

  靛红 在 对甲苯磺酸 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 1,2,3,4-tetrahydro-1-oxoacridine-9-carboxylic acid
  参考文献：
  名称：

  Synthesis of 6,7-Dihydrodibenzo[b,j]phenanthroline Derivatives by Pfitzinger Condensation of Isatin and Cyclic Diketones

  摘要：

  All two kinds of 6,7-dihydrodibenzo[b,j]phenanthroline derivatives were synthesized by Pfitzinger condensation of isatins with 1,3-cyclohexanedione and 1,4-cyclohexanedione respectively. Structures of the derivatives were confirmed by NMR and other spectra data.

  DOI：

  10.3987/com-13-12894

文献信息

• A simple one-pot synthesis of quinoline-4-carboxylic acid derivatives by Pfitzinger reaction of isatin with ketones in water
  作者：Qinghua Lv、Lizhen Fang、Pengfei Wang、Chenjuan Lu、Fulin Yan

  DOI：10.1007/s00706-012-0822-5

  日期：2013.3

  AbstractAn improved Pfitzinger condensation reaction performed under acidic conditions is established. It provides a simple and efficient synthetic method for some useful quinoline-4-carboxylic acid derivatives using isatins and ketones that cannot be obtained easily under ordinary conditions. The generality of this methodology and the catalysts used for this protocol are explored in this paper. Structures

  摘要建立了在酸性条件下进行的改进的Pfitzinger缩合反应。它为使用某些在常规条件下不易获得的靛红和酮为有用的喹啉-4-羧酸衍生物提供了一种简单有效的合成方法。本文探讨了该方法的一般性以及用于该方案的催化剂。所有合成化合物的结构均通过光谱数据表征。 图形概要
• Improved Synthesis of 1-Oxo-1,2,3,4-tetrahydroacridine-9-carboxylic Acids from Isatins and 1,3-Cyclohexanedione
  作者：Lizhen Fang、Qinghua Lv、Chenjuan Lu、Pengfei Wang

  DOI：10.3987/com-12-12479

  日期：——

  An improved protocol for the preparation of 1-oxo-1,2,3,4-tetrahydroacridine-9-carboxylic acid derivatives via Pfitzinger condensation under acidic conditions is described, it provides a simple one-pot synthetic method for some useful 1-oxo-1,2,3,4-tetrahydroacridine-9-carboxylic acids which could not be synthesized successfully by Pfitzinger reactions under usual conditions using the corresponding isatins and 1,3-diketones. All the synthesized compounds are characterized by spectral data.
• Synthesis of 6,7-Dihydrodibenzo[b,j]phenanthroline Derivatives by Pfitzinger Condensation of Isatin and Cyclic Diketones
  作者：Lizhen Fang、Jinshuo Ma、Chenjuan Lu、Huanhuan Li、Xiaoli Yang

  DOI：10.3987/com-13-12894

  日期：——

  All two kinds of 6,7-dihydrodibenzo[b,j]phenanthroline derivatives were synthesized by Pfitzinger condensation of isatins with 1,3-cyclohexanedione and 1,4-cyclohexanedione respectively. Structures of the derivatives were confirmed by NMR and other spectra data.