2-[(E)-1-(1,2-dimethyl-3-indolyl)ethylidene]-3-isopropylidene succinic anhydride | 119167-83-8

• 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-[(E)-1-(1,2-dimethyl-3-indolyl)ethylidene]-3-isopropylidene succinic anhydride
• 英文别名: (3Z)-3-[1-(1,2-dimethylindol-3-yl)ethylidene]-4-propan-2-ylideneoxolane-2,5-dione
• CAS: 119167-83-8
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: DUCPSKDZEJTXFR-BOPFTXTBSA-N

物化性质

• 沸点：
  498.1±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 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：
  3

反应信息

• 作为反应物：
  描述：

  2-[(E)-1-(1,2-dimethyl-3-indolyl)ethylidene]-3-isopropylidene succinic anhydride 以 甲苯 为溶剂， 生成 methyl indolylfulgide
  参考文献：
  名称：

  Fulgenolides. Thermally Irreversible Photochromic Lactones with Large Quantum Yields of Photoreactions

  摘要：

  我们合成了三种与一种吲哚富甙密切相关的新型光致变色内酯。羰基与异亚丙基相邻的内酯具有较大的光反应量子产率，而羰基与吲哚亚乙基相邻的异构体的光致变色性能较差。有色内酯的吸收最大值比吲哚乙酰基的吸收最大值短。

  DOI：

  10.1246/cl.1995.17
• 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 2-[(E)-1-(1,2-dimethyl-3-indolyl)ethylidene]-3-isopropylidene succinic anhydride
  参考文献：
  名称：

  Improved Synthesis of Indolyl Fulgides

  摘要：

  DOI：

  10.1021/jo005722n

文献信息

• Fulgimide derivatives
  申请人：Wako Pure Chemical Industries, Ltd.

  公开号：US05359085A1

  公开（公告）日：1994-10-25

  A fulgimide derivative of the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 are independently alkyl cycloalkyl aryl etc.; R.sup.4 is thienyl, indolyl, furyl, etc.; X is a divalent organic residue; and R is amino, OH, etc., or a vinyl group, has a photochromic action and can be used for producing photochromic polymers and copolymers.

  公式为：##STR1##的富尔吉酰亚胺衍生物，其中R.sup.1、R.sup.2、R.sup.3分别是烷基、环烷基、芳基等；R.sup.4是噻吩基、吲哚基、呋喃基等；X是二价有机残基；R是氨基、羟基等，或乙烯基，具有光致变色作用，可用于制备光致变色聚合物和共聚物。
• 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。
• Steric Effects of Substituents on the Photochromism of Indolylfulgides
  作者：Soichi Uchida、Shintaro Yamada、Yasushi Yokoyama、Yukio Kurita

  DOI：10.1246/bcsj.68.1677

  日期：1995.6

  with a bulky 1-alkyl-1-indolylmethylidene and/or a bulky alkylidene substituent were synthesized and their photochromic as well as absorption spectroscopic properties were compared with those of the known prototype indolylfulgide, 3-[1-(1,2-dimethyl-3-indolyl)ethylidene]-4-isopropylidenedihydro-2,5-furandione. An increase in steric bulkiness of the alkyl group (R1) on the indolylmethylidene group increased

  合成了具有庞大的 1-烷基-1-吲哚基亚甲基和/或庞大的亚烷基取代基的光致变色富酸酐，并将它们的光致变色和吸收光谱性质与已知原型吲哚基富酸酐、3-[1-(1,2-二甲基-3-吲哚基)亚乙基]-4-异亚丙基二氢-2,5-呋喃二酮。吲哚亚甲基上烷基 (R1) 的空间体积增加增加了着色量子产率 (ΦEC = 0.046 (R1 = 甲基) 至 0.31 (R1 = 异丙基))，而其他亚烷基的空间体积增加组 (R2) 增加了漂白量子产率 (ΦCE = 0.051 (R2 = 异丙叉) 到 0.42 (R2 = 2-金刚烷基))。然而，当 R1 和 R2 都很大时，着色量子产率并不大，尽管漂白量子产率仍然很大。
• Fulgenates. A New Class of Fulgide-Related Thermally Irreversible Photochromic System
  作者：Yasushi Yokoyama、Kazuhiro Sugiyama、Shintaro Yamada、Hitoshi Takimoto、Yukio Kurita

  DOI：10.1246/cl.1994.749

  日期：1994.4

  Thermally irreversible photochromic properties of indolylfulgenates, i.e. 2-alkylidene-3-[1-(1,2-dimethyl-3-indolyl)alkylidene]succinate esters were examined. A large indolylalkylidene group reduced the relative ratio of the colored species at the photostationary state of UV irradiation. Introduction of an adamantylidene group increased the bleaching quantum yield. The absorption maximum wavelengths

  检测了吲哚基富根酸盐，即 2-亚烷基-3-[1-(1,2-二甲基-3-吲哚基) 亚烷基]琥珀酸酯的热不可逆光致变色性能。大的吲哚亚烷基降低了在紫外线照射的光稳定状态下有色物质的相对比例。金刚烷基的引入增加了漂白量子产率。无色和有色物质的最大吸收波长短于相应的吲哚氟酸。
• A Liquid Crystal Opto-optical Switch: Nondestructive Information Retrieval Based on a Photochromic Fulgide as Trigger
  作者：Slawomir Z. Janicki、Gary B. Schuster

  DOI：10.1021/ja00138a005

  日期：1995.8

  Liquid crystals are a unique medium for sensing small structural changes in their environment. Cholesteric liquid crystals respond to these forces by changing their pitch. A photochromic dopant in a cholesteric liquid crystal was used to translate optical input to observable pitch change. The change is reversible solely by action of light, and a cyclic mode of operation is demonstrated. The information encoded by light can be read optically without its destruction. The doped liquid crystal system does not show fatigue during the course of these experiments.