(3Z)-1-(dimethylamino)-3-[1-(1,2-dimethylindol-3-yl)-2,2,2-trifluoroethylidene]-4-propan-2-ylidenepyrrolidine-2,5-dione | 496951-20-3

• 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: (3Z)-1-(dimethylamino)-3-[1-(1,2-dimethylindol-3-yl)-2,2,2-trifluoroethylidene]-4-propan-2-ylidenepyrrolidine-2,5-dione
• CAS: 496951-20-3
• 化学式: C₂₁H₂₂F₃N₃O₂
• 分子量: 405.42
• InChiKey: XTEDINBXHPYKLD-ZCXUNETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3Z)-1-(dimethylamino)-3-[1-(1,2-dimethylindol-3-yl)-2,2,2-trifluoroethylidene]-4-propan-2-ylidenepyrrolidine-2,5-dione 以 甲苯 为溶剂， 生成 2-Dimethylamino-4,4,4a,5-tetramethyl-10-trifluoromethyl-4a,5-dihydro-4H-pyrrolo[3,4-b]carbazole-1,3-dione
  参考文献：
  名称：

  Tuning the Optical Properties of Fluorinated Indolylfulgimides

  摘要：

  Photochromic fluorinated indolylfulgides have been identified as potential candidates for a wide range of applications including optical switches, photoregulators of biological processes, and optical memory media. In humid environments or biological systems, hydrolytic stability is essential. In an effort to improve hydrolytic stability, a series of indolylfulgimides has been synthesized from a parent trifluoromethyl-substituted indolylfulgide. The nitrogen of the succinimide moiety is linked to either a dimethyl amino or one of seven substituted phenyl groups. The phenyl groups feature substituents with increasing electron-withdrawing ability. The spectral characteristics of each compound have been examined, revealing that the wavelength absorption maxima of each form increases with increasing electron-withdrawing ability of the substituted N-phenyl ring. The quantum yields of the photoreactions have been determined with the N-(phenyl)fulgimide showing a ring closure value of nearly 0.30 in toluene. In addition, the hydrolytic, thermal, and photochemical stabilities of each compound have been measured. The fulgimides exhibit at least a 200-fold enhancement of hydrolytic stability for the Z-form and over a 1000-fold enhancement for the C-form in comparison to the same form of the parent fulgide. The N-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)fulgimide can undergo up to 3000 photochemical cycles (coloration followed by bleaching) before losing 20% of its initial absorbance at photostationary state.

  DOI：

  10.1021/jo026374n
• 作为产物：
  描述：

  2-Dimethylamino-4,4,4a,5-tetramethyl-10-trifluoromethyl-4a,5-dihydro-4H-pyrrolo[3,4-b]carbazole-1,3-dione 以 甲苯 为溶剂， 以100%的产率得到(3Z)-1-(dimethylamino)-3-[1-(1,2-dimethylindol-3-yl)-2,2,2-trifluoroethylidene]-4-propan-2-ylidenepyrrolidine-2,5-dione
  参考文献：
  名称：

  Tuning the Optical Properties of Fluorinated Indolylfulgimides

  摘要：

  Photochromic fluorinated indolylfulgides have been identified as potential candidates for a wide range of applications including optical switches, photoregulators of biological processes, and optical memory media. In humid environments or biological systems, hydrolytic stability is essential. In an effort to improve hydrolytic stability, a series of indolylfulgimides has been synthesized from a parent trifluoromethyl-substituted indolylfulgide. The nitrogen of the succinimide moiety is linked to either a dimethyl amino or one of seven substituted phenyl groups. The phenyl groups feature substituents with increasing electron-withdrawing ability. The spectral characteristics of each compound have been examined, revealing that the wavelength absorption maxima of each form increases with increasing electron-withdrawing ability of the substituted N-phenyl ring. The quantum yields of the photoreactions have been determined with the N-(phenyl)fulgimide showing a ring closure value of nearly 0.30 in toluene. In addition, the hydrolytic, thermal, and photochemical stabilities of each compound have been measured. The fulgimides exhibit at least a 200-fold enhancement of hydrolytic stability for the Z-form and over a 1000-fold enhancement for the C-form in comparison to the same form of the parent fulgide. The N-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)fulgimide can undergo up to 3000 photochemical cycles (coloration followed by bleaching) before losing 20% of its initial absorbance at photostationary state.

  DOI：

  10.1021/jo026374n

文献信息

• Tuning the Optical Properties of Fluorinated Indolylfulgimides
  作者：Mason A. Wolak、Craig J. Thomas、Nathan B. Gillespie、Robert R. Birge、Watson J. Lees

  DOI：10.1021/jo026374n

  日期：2003.1.1

  Photochromic fluorinated indolylfulgides have been identified as potential candidates for a wide range of applications including optical switches, photoregulators of biological processes, and optical memory media. In humid environments or biological systems, hydrolytic stability is essential. In an effort to improve hydrolytic stability, a series of indolylfulgimides has been synthesized from a parent trifluoromethyl-substituted indolylfulgide. The nitrogen of the succinimide moiety is linked to either a dimethyl amino or one of seven substituted phenyl groups. The phenyl groups feature substituents with increasing electron-withdrawing ability. The spectral characteristics of each compound have been examined, revealing that the wavelength absorption maxima of each form increases with increasing electron-withdrawing ability of the substituted N-phenyl ring. The quantum yields of the photoreactions have been determined with the N-(phenyl)fulgimide showing a ring closure value of nearly 0.30 in toluene. In addition, the hydrolytic, thermal, and photochemical stabilities of each compound have been measured. The fulgimides exhibit at least a 200-fold enhancement of hydrolytic stability for the Z-form and over a 1000-fold enhancement for the C-form in comparison to the same form of the parent fulgide. The N-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)fulgimide can undergo up to 3000 photochemical cycles (coloration followed by bleaching) before losing 20% of its initial absorbance at photostationary state.