3-furylfulgide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-furylfulgide
• 英文别名: (e)-2-[1-(2,5-Dimethyl-3-furyl)ethylidene]-3-isopropylidenesuccinic anhydride；(3E)-3-[1-(2,5-dimethylfuran-3-yl)ethylidene]-4-propan-2-ylideneoxolane-2,5-dione
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: ITMSLXOTORBGQJ-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-furylfulgide 在 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 75.0h， 生成
  参考文献：
  名称：

  Probing Poly(n-butyl-methacrylate) Latex Film via Diffusion of Hydrophilic and Hydrophobic Dye Molecules

  摘要：

  In the study of holographic grating relaxation (forced Rayleigh scattering, FRS) in nascent latex films we examined poly(n-butyl methacrylate) films using two complementary diffusing probes: a hydrophobic fulgide, Aberchrome-540, and its hydrophilic salt derivative. In the former case, the grating decay follows a stretched exponential. Data analysis in terms of a two-state diffusion model yields tracer diffusion coefficients in the cores of the latex particles (10(-16) m(2) s(-1)) and the hydroplasticized interface meshes that surround them (10(-13) m(2) s(-1)). In the case of the hydrophilic tracer several distinct stages of grating decay can be isolated and interpreted as representing the dye diffusion in water (10(-10) m(2) s(-1)), in the interfaces (10(-13) m(2) s(-1)), in polymer cores (10(-16) m(2) s(-1)), and captured by surfactant clusters (10(-19) m(2) s(-1)), respectively. The contributions of particular environments depend on tracer hydrophilicity. Therefore, the two dyes employed provide complementary information on different types of spatial domains in mesoscopically heterogeneous latex films.

  DOI：

  10.1021/ma0258962
• 作为产物：
  描述：

  二乙基异亚丙基琥珀酸酯 在 N,N'-二环己基碳二亚胺 、 potassium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正庚烷 、 二氯甲烷 、 乙基苯 、 水 为溶剂， 反应 69.0h， 生成 3-furylfulgide
  参考文献：
  名称：

  受空间改性影响的旋转受阻呋喃磺酰化物的光致变色

  摘要：

  描述了具有增加的空间限制的双环呋喃基酸酐 14 和 (苯并呋喃基) 缩醛酸酐 15 的合成。通过紫外/可见光谱测量、X 射线晶体学和核磁共振实验分析了它们的光致变色行为，并将结果与​​呋喃 (甲基) 富酸酐 12 和呋喃 (异丙基) 富酸酐 13 的结果进行了比较。 化合物 13E 和与12E和15E（0.23和0.17）相比，14E的显色反应（E）->（C）表现出0.57和0.53的大量子产率。在用 350 nm 光照射后，13E 和 14E 几乎定量地转化为封闭的 (C) 形式，而 12E 和 15E 导致具有 (E)、(Z) 和 (C) 形式的混合物的光稳定状态。13E、14E、图 15E 和 15E 表明，硫化物采用可环化的螺旋 (P)-E(alpha) 构象，在己三烯单元中的原子距离没有显着差异。二维和温度依赖性 NMR 实验表明，对映异构化和非对映异构化过程首次在 fulgide

  DOI：

  10.1002/ejoc.201001649

文献信息

• Photochromic heterocyclic fulgides. Part 2. Electrocyclic reactions of (E)-α-2,5-dimethyl-3-furylethylidene(alkyl-substituted methylene)succinic anhydrides
  作者：Paul J. Darcy、Harry G. Heller、Peter J. Strydom、John Whittall

  DOI：10.1039/p19810000202

  日期：——

  undergo reversible photochemical conrotatory electrocyclic reactions to give in quantitative yields deep red 7,7a-dihydrobenzo[b]furan-5,6-dicarboxylic anhydrides, which are stable at 100 °C. These photochromic systems, which have high quantum yields for photocolouration, are highly resistant to photodegradation and retain their photochromic properties in a variety of solvents.

  浅黄色标题化合物经过可逆的光化学旋转电环反应，定量获得深红色的7,7a-二氢苯并[ b ]呋喃-5,6-二羧酸酐，其在100°C下稳定。这些用于光致变色的量子产率高的光致变色体系具有高度的耐光降解性，并在各种溶剂中保持其光致变色特性。
• Effects of Steric Bulkiness of Substituents on Quantum Yields of Photochromic Reactions of Furylfulgides
  作者：Yasushi Yokoyama、Tetsushi Inoue、Masato Yokoyama、Takakazu Goto、Takeshi Iwai、Naohiko Kera、Isamu Hitomi、Yukio Kurita

  DOI：10.1246/bcsj.67.3297

  日期：1994.12

  Furylfulgides with different sizes of alkyl substituents were synthesized and their photochromic properties were examined. While the quantum yield of coloring reaction increased and the quantum yield of the E-to-Z isomerization decreased as the steric bulkiness of the alkyl substitutent on the 2,5-dimethyl-3-furylmethylidene moiety increased, the bleaching quantum yield increased as the isopropylidene

  合成了具有不同大小烷基取代基的呋喃磺酰氯并检测了它们的光致变色性能。虽然随着 2,5-二甲基-3-呋喃亚甲基部分上烷基取代基的空间体积增加，着色反应的量子产率增加，E-to-Z 异构化的量子产率降低，但漂白量子产率随着异亚丙基被金刚烷基取代。两种效应独立起作用，并且在一个分子中具有异丙基的呋喃亚甲基部分和金刚烷亚基的呋喃酰氟酸在甲苯中显示出 0.51 (366 nm) 的着色量子产率和 0.26 (492 nm) 的漂白量子产率。
• Synthesis and Photochromic Properties of Fulgides with a<i>t</i>-Butyl Substituent on the Furyl- or Thienylmethylidene Moiety
  作者：Jitsuo Kiji、Tamon Okano、Hitoshi Kitamura、Yasushi Yokoyama、Shuji Kubota、Yukio Kurita

  DOI：10.1246/bcsj.68.616

  日期：1995.2

  as the catalyst. The reaction at 90 °C under 80 atm of carbon monoxide for 5 h directly gave both E and Z isomers of t-butyl-substituted furyl- or thienyl fulgides. The former had been reported impossible to synthesize by the Stobbe condensation. Similarly, furyl- and thienylfulgides with an isopropyl group were synthesized by this method. The fulgides were isolated by column chromatography in 37—75%

  2,6,6-三甲基-5-(2,5-二甲基-3-呋喃基和-3-噻吩基)-3-庚炔-2,5-二醇在苯中在 1:1-Pd( OAc)2/I2 作为催化剂。在 90°C 和 80 个大气压的一氧化碳下反应 5 小时，直接得到叔丁基取代的呋喃基或噻吩基强酸酐的 E 和 Z 异构体。据报道，前者不可能通过 Stobbe 缩合合成。类似地，通过这种方法合成了带有异丙基的呋喃基和噻吩基硫辛酸。通过柱层析分离出产率为 37-75% 的强酸酐。叔丁基-呋喃基-和-噻吩基强酸酐的着色量子产率分别为0.79和0.73，在具有相同杂芳环的各系列强酸酐中最高。
• Fulgides as Efficient Photochromic Compounds. Role of the Substituent on Furylalkylidene Moiety of Furylfulgides in the Photoreaction
  作者：Yasushi Yokoyama、Takakazu Goto、Tetsushi Inoue、Masato Yokoyama、Yukio Kurita

  DOI：10.1246/cl.1988.1049

  日期：1988.6.5

  Quantum yields of photoreactions of furylfulgides having Me, Et, n-Pr, or i-Pr on the furylalkylidene moiety were measured. The E–Z isomerization was greatly suppressed and the cyclization was accelerated when the alkyl group (R) became bulkier. When R was i-Pr, no E–Z isomerization was observed and the quantum yield of the colorizing cyclization was 0.62.

  测量了在呋喃基亚烷基部分上具有 Me、Et、n-Pr 或 i-Pr 的呋喃基硫酰化物的光反应的量子产率。当烷基 (R) 变得更大时，E-Z 异构化被大大抑制，环化加速。当 R 为 i-Pr 时，未观察到 E-Z 异构化，着色环化的量子产率为 0.62。
• Synthesis and photochromism of 1,2-bis(5-aryl-2-phenylethynylthien-3-yl)hexafluorocyclopentene derivatives
  作者：Jianxin Cai、Amani Farhat、Pavel B. Tsitovitch、Vivek Bodani、R. Daniel Toogood、R. Scott Murphy

  DOI：10.1016/j.jphotochem.2010.04.013

  日期：2010.5

  Photochromic dithienylethenes that possess elements of lipid complementarity, and undergo large, photoinduced changes in molecular geometry have been prepared. Further, a regioselective approach has been developed for the preparation of dithienylethenes containing phenylethynyl and various aryl substituents at C2 and C5 of the thiophene moieties, respectively. The prepared photochromic compounds were

  已经制备了具有脂质互补元素并经历了分子几何中的大的光诱导变化的光致变色二噻吩基乙烯。此外，已经开发了区域选择性方法用于制备分别在噻吩部分的C 2和C 5处含有苯基乙炔基和各种芳基取代基的二噻吩基乙烯。观察到制备的光致变色化合物经历可逆的光异构化。它们的吸收性质，反应的量子产率，并且在photoconversions测定Ñ正己烷。