(3E)-3-[1-(1,2-dimethylindol-3-yl)-2,2,2-trifluoroethylidene]-4-propan-2-ylideneoxolane-2,5-dione | 186258-16-2

• 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: (3E)-3-[1-(1,2-dimethylindol-3-yl)-2,2,2-trifluoroethylidene]-4-propan-2-ylideneoxolane-2,5-dione
• CAS: 186258-16-2
• 化学式: C₁₉H₁₆F₃NO₃
• 分子量: 363.336
• InChiKey: ZIMWHTGSJJTJIG-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3E)-3-[1-(1,2-dimethylindol-3-yl)-2,2,2-trifluoroethylidene]-4-propan-2-ylideneoxolane-2,5-dione 以 甲苯 为溶剂， 生成 (3Z)-3-[1-(1,2-dimethyl-1H-indol-3-yl)-2,2,2-trifluoroethylidene]-4-(1-methylethylidene)dihydrofuran-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
• 作为产物：
  描述：

  二乙基异亚丙基琥珀酸酯 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 25.17h， 生成 (3E)-3-[1-(1,2-dimethylindol-3-yl)-2,2,2-trifluoroethylidene]-4-propan-2-ylideneoxolane-2,5-dione
  参考文献：
  名称：

  Improved Synthesis of Indolyl Fulgides

  摘要：

  DOI：

  10.1021/jo005722n

文献信息

• Trifluoromethyl-substituted Photochromic Indolylfulgide. A Remarkably Durable Fulgide towards Photochemical and Thermal Treatments
  作者：Yasushi Yokoyama、Kazuyuki Takahashi

  DOI：10.1246/cl.1996.1037

  日期：1996.12

  An indolylfulgide having a 1-(1,2-dimethyl-3-indolyl)-2,2,2-trifluoroethylidene group on the succinic anhydride showed an excellent resistivity towards the repetition of photochromic transformation between the photostationary states of UV- and visible-light irradiation both in toluene and in a PMMA film under the atmospheric environment. The colored form also showed the remarkable thermal stability.

  一种在琥珀酸酐上具有 1-（1,2-二甲基-3-吲哚基）-2,2,2-三氟亚乙基的吲哚乙酰苷在甲苯中和大气环境下的 PMMA 薄膜中对紫外线和可见光照射下的光致变色态之间的重复光致变色转换表现出极佳的电阻率。这种有色形态还具有显著的热稳定性。
• Thermolysis of a Fluorinated Indolylfulgide Features a Novel 1,5-Indolyl Shift
  作者：Mason A. Wolak、Jeremy M. Sullivan、Craig J. Thomas、Robert C. Finn、Robert R. Birge、Watson J. Lees

  DOI：10.1021/jo015693w

  日期：2001.6.1
• 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.
• Improved Synthesis of Indolyl Fulgides
  作者：Craig J. Thomas、Mason A. Wolak、Robert R. Birge、Watson J. Lees

  DOI：10.1021/jo005722n

  日期：2001.3.1