2-(2-amino-4-nitrophenyl)benzo[d,e]isoquinoline-1,3-dione | 1035441-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-amino-4-nitrophenyl)benzo[d,e]isoquinoline-1,3-dione
• 英文别名: 2-(2-Amino-4-nitrophenyl)benzo[de]isoquinoline-1,3-dione；2-(2-amino-4-nitrophenyl)benzo[de]isoquinoline-1,3-dione
• CAS: 1035441-19-0
• 化学式: C₁₈H₁₁N₃O₄
• 分子量: 333.303
• InChiKey: SNOOBRNGUHWHKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,8-萘二甲酸酐 、 4-硝基邻苯二胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-(2-amino-4-nitrophenyl)benzo[d,e]isoquinoline-1,3-dione
  参考文献：
  名称：

  Solvation controlling reaction paths and gel-formation in imide derivatives

  摘要：

  1,8-Naphthalic anhydride condenses with 4-nitro-1,2-diaminobenzene in acetic acid to give 11-nitrobenzo[d,e]benzo[2,1-a]isoquinoline-1,3-dione (1), whereas the same reaction carried out in DMF gives 2-(2-amino-4-nitrophenyl)-benzo[d,e]isoquinoline-1,3-dione (2). The condensation reaction of 1,8-naphthalic anhydride with 1-amino 3,5-benzene dicarboxylic acid leads to corresponding imide, which forms a gel in a mixed solvent such as water in DMSO. A similar compound 5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-isophthalic acid derived from phthalic anhydride forms gel in a mixed solvent of DMSO and water, whereas a crystalline solvate of DMSO with 2 could be obtained upon crystallization from DMSO. The crystal structure of this solvate is determined and its structure is compared with 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-benzoic acid. The latter does not form a gel in the mixed solvent and adopts an intermolecular hydrogen bonded structure. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.030

文献信息

• Solvation controlling reaction paths and gel-formation in imide derivatives
  作者：Devendra Singh、Jubaraj B. Baruah

  DOI：10.1016/j.tetlet.2008.05.030

  日期：2008.7

  1,8-Naphthalic anhydride condenses with 4-nitro-1,2-diaminobenzene in acetic acid to give 11-nitrobenzo[d,e]benzo[2,1-a]isoquinoline-1,3-dione (1), whereas the same reaction carried out in DMF gives 2-(2-amino-4-nitrophenyl)-benzo[d,e]isoquinoline-1,3-dione (2). The condensation reaction of 1,8-naphthalic anhydride with 1-amino 3,5-benzene dicarboxylic acid leads to corresponding imide, which forms a gel in a mixed solvent such as water in DMSO. A similar compound 5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-isophthalic acid derived from phthalic anhydride forms gel in a mixed solvent of DMSO and water, whereas a crystalline solvate of DMSO with 2 could be obtained upon crystallization from DMSO. The crystal structure of this solvate is determined and its structure is compared with 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-benzoic acid. The latter does not form a gel in the mixed solvent and adopts an intermolecular hydrogen bonded structure. (C) 2008 Elsevier Ltd. All rights reserved.