2-(carboxymethyl)-4,4,4a,5-tetramethyl-1,3-dioxo-1,2,3,4,4a,5-hexahydropyrrolo[3,4-b]carbazole-10-carboxylic acid | 1182714-59-5

• 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: 2-(carboxymethyl)-4,4,4a,5-tetramethyl-1,3-dioxo-1,2,3,4,4a,5-hexahydropyrrolo[3,4-b]carbazole-10-carboxylic acid
• 英文别名: 2-(Carboxymethyl)-9,9a,10,10-tetramethyl-1,3-dioxopyrrolo[3,4-b]carbazole-4-carboxylic acid
• CAS: 1182714-59-5
• 化学式: C₂₁H₂₀N₂O₆
• 分子量: 396.4
• InChiKey: QHAKZHSXXVVPMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(carboxymethyl)-4,4,4a,5-tetramethyl-1,3-dioxo-1,2,3,4,4a,5-hexahydropyrrolo[3,4-b]carbazole-10-carboxylic acid 生成 (2Z)-2-[1-(carboxymethyl)-2,5-dioxo-4-propan-2-ylidenepyrrolidin-3-ylidene]-2-(1,2-dimethylindol-3-yl)acetic acid
  参考文献：
  名称：

  Synthesis and Optical Properties of Aqueous Soluble Indolylfulgimides

  摘要：

  Three novel aqueous soluble fulgimides, trifluoromethyl carboxylic acid indolylfulgimide 4, dicarboxylic acid indolylfulgimide 5, and carboxylic acid indolylfulgimide 6, were synthesized. Both 4 and 5 can switch back and forth between open and closed forms upon illumination with specific wavelengths of light, whereas 6 can only switch from the closed form to the open form. In sodium phosphate buffer (pH 7.4) at 37 degrees C, an unusual hydrolysis of the trifluoromethyl group of the closed form of 4 resulted in 5, which has an additional carboxylic acid group. The closed form of 5 was further decarboxylated to generate 6, which was not photochromic. In buffer, the open form of 4 degraded 20% after 10 days, while the closed form of 4 was converted to 5 rapidly. In buffer, both forms of 5 degraded less than 20% after 21 days at 37 degrees C, and 5 underwent 670 photochemical cycles before degrading by 20%, It is the most robust fulgimide yet reported in aqueous solution.

  DOI：

  10.1021/jo900909d
• 作为产物：
  描述：

  2-[9,9a,10,10-Tetramethyl-1,3-dioxo-4-(trifluoromethyl)pyrrolo[3,4-b]carbazol-2-yl]acetic acid 反应 12.0h， 以42%的产率得到2-(carboxymethyl)-4,4,4a,5-tetramethyl-1,3-dioxo-1,2,3,4,4a,5-hexahydropyrrolo[3,4-b]carbazole-10-carboxylic acid
  参考文献：
  名称：

  Synthesis and Optical Properties of Aqueous Soluble Indolylfulgimides

  摘要：

  Three novel aqueous soluble fulgimides, trifluoromethyl carboxylic acid indolylfulgimide 4, dicarboxylic acid indolylfulgimide 5, and carboxylic acid indolylfulgimide 6, were synthesized. Both 4 and 5 can switch back and forth between open and closed forms upon illumination with specific wavelengths of light, whereas 6 can only switch from the closed form to the open form. In sodium phosphate buffer (pH 7.4) at 37 degrees C, an unusual hydrolysis of the trifluoromethyl group of the closed form of 4 resulted in 5, which has an additional carboxylic acid group. The closed form of 5 was further decarboxylated to generate 6, which was not photochromic. In buffer, the open form of 4 degraded 20% after 10 days, while the closed form of 4 was converted to 5 rapidly. In buffer, both forms of 5 degraded less than 20% after 21 days at 37 degrees C, and 5 underwent 670 photochemical cycles before degrading by 20%, It is the most robust fulgimide yet reported in aqueous solution.

  DOI：

  10.1021/jo900909d

文献信息

• Synthesis and Optical Properties of Aqueous Soluble Indolylfulgimides
  作者：Xi Chen、Nadezhda I. Islamova、Sandra P. Garcia、Jessica A. DiGirolamo、Watson J. Lees

  DOI：10.1021/jo900909d

  日期：2009.9.4

  Three novel aqueous soluble fulgimides, trifluoromethyl carboxylic acid indolylfulgimide 4, dicarboxylic acid indolylfulgimide 5, and carboxylic acid indolylfulgimide 6, were synthesized. Both 4 and 5 can switch back and forth between open and closed forms upon illumination with specific wavelengths of light, whereas 6 can only switch from the closed form to the open form. In sodium phosphate buffer (pH 7.4) at 37 degrees C, an unusual hydrolysis of the trifluoromethyl group of the closed form of 4 resulted in 5, which has an additional carboxylic acid group. The closed form of 5 was further decarboxylated to generate 6, which was not photochromic. In buffer, the open form of 4 degraded 20% after 10 days, while the closed form of 4 was converted to 5 rapidly. In buffer, both forms of 5 degraded less than 20% after 21 days at 37 degrees C, and 5 underwent 670 photochemical cycles before degrading by 20%, It is the most robust fulgimide yet reported in aqueous solution.