(3Z)-3-[1-(1,2-dimethyl-1H-indol-3-yl)-2,2,2-trifluoroethylidene]-4-(1-methylethylidene)dihydrofuran-2,5-dione | 186258-15-1

• 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)-3-[1-(1,2-dimethyl-1H-indol-3-yl)-2,2,2-trifluoroethylidene]-4-(1-methylethylidene)dihydrofuran-2,5-dione
• 英文别名: trifluoromethylisopropylideneindolylfulgide；PSS-570；(3Z)-3-[1-(1,2-dimethylindol-3-yl)-2,2,2-trifluoroethylidene]-4-propan-2-ylideneoxolane-2,5-dione
• CAS: 186258-15-1
• 化学式: C₁₉H₁₆F₃NO₃
• 分子量: 363.336
• InChiKey: ZIMWHTGSJJTJIG-NXVVXOECSA-N

物化性质

• 沸点：
  510.1±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

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：

  (3Z)-3-[1-(1,2-dimethyl-1H-indol-3-yl)-2,2,2-trifluoroethylidene]-4-(1-methylethylidene)dihydrofuran-2,5-dione 以 甲苯 为溶剂， 生成 3-[1-(1,2-Dimethyl-1H-indol-3-yl)-2,2,2-trifluoro-ethyl]-4-isopropenyl-furan-2,5-dione
  参考文献：
  名称：

  Thermolysis of a Fluorinated Indolylfulgide Features a Novel 1,5-Indolyl Shift

  摘要：

  DOI：

  10.1021/jo015693w
• 作为产物：
  描述：

  1-(1,2-dimethyl-1H-indol-3-yl)-2,2,2-trifluoroethan-1-one 在 氢氧化钾 作用下， 以 甲醇 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：

  Trifluoromethyl-substituted Photochromic Indolylfulgide. A Remarkably Durable Fulgide towards Photochemical and Thermal Treatments

  摘要：

  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。

  DOI：

  10.1246/cl.1996.1037

文献信息

• Ring-opening reaction of a trifluorinated indolylfulgide: mode-specific photochemistry after pre-excitation
  作者：Simone Draxler、Thomas Brust、Stephan Malkmus、Jessica A. DiGirolamo、Watson J. Lees、Wolfgang Zinth、Markus Braun

  DOI：10.1039/b819585d

  日期：——

  The ring-opening reaction of a trifluorinated indolylfulgide has been studied as a function of temperature and optical pre-excitation where it was found that reaction times decreased as temperature increased from 10.3 ps at 12 °C to 7.6 ps at 60 °C. Simultaneously, the quantum yields for the ring-opening reaction grew from 3.1% (12 °C) to 5.0% (60 °C). When the reaction was started from a non-equilibrium state generated by a directly preceding ring-closure process, the ring-opening reaction became faster and the quantum efficiency increased by more than a factor of three. Analysis of the experimental results points to mode-specific photochemistry in that the promoting, photochemically active modes of the photoreaction are efficiently excited by the directly preceding ring-closure reaction.

  我们研究了一种三氟吲哚乙酰苷的开环反应与温度和光学预激发的函数关系，发现反应时间随着温度的升高而缩短，从 12 ℃ 时的 10.3 ps 缩短到 60 ℃ 时的 7.6 ps。同时，开环反应的量子产率从 3.1%（12 °C）增至 5.0%（60 °C）。当反应从直接先于闭环过程产生的非平衡态开始时，开环反应变得更快，量子效率提高了三倍以上。对实验结果的分析表明了特定模式的光化学作用，即光反应中的促进模式、光化学活性模式被直接在前的开环反应有效激发。
• 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.
• 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.
• 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