(E)-dicyclopropylidene(2,5-dimethyl-3-furyl)ethylidenesuccinic anhydride | 152715-50-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-dicyclopropylidene(2,5-dimethyl-3-furyl)ethylidenesuccinic anhydride
• 英文别名: (E)-4-dicyclopropylmethylene-3-[1-(2,5-dimethylfuryl)ethylidene]tetrahydrofuran-2,5-dione；(E)-3-[1-(2,5-Dimethyl-3-furyl)ethylidene]-4-(dicyclopropylmethylene)tetrahydrofuran-2,5-dione；(E)-3-(dicyclopropylmethylene)-dihydro-4-[1-(2,5 dimethylfuran-3-yl)ethylidene]furan-2,5-dione；(4E)-3-(dicyclopropylmethylidene)-4-[1-(2,5-dimethylfuran-3-yl)ethylidene]oxolane-2,5-dione
• CAS: 152715-50-9
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: FZKPXLWLLPOXPG-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (E)-dicyclopropylidene(2,5-dimethyl-3-furyl)ethylidenesuccinic anhydride 在 乙酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (E)-5-dicyanomethylene-4-dicyclopropylmethylene-3-[1-(2,5-dimethylfuryl)ethylidene]tetrahydrofuran-2-one
  参考文献：
  名称：

  光致变色单体：通过增强共轭的结构修饰，将非致变剂的非光致变色（Z）异构体转变为高度光致变色（E）异构体

  摘要：

  非光致变色的fulgide（1-Z）已成功转化为高光致变色的（3-Z）类似物。在1-Z的5位引入一个二氰基亚甲基，以增强后者的共轭性能，从而促进光化学Z→E异构化过程。用在λmax 350 nm处的紫外线照射产物3-Z形成蓝绿色溶液，该溶液在λmax 620 nm处吸收，对应于闭环产物4。后者也由参比双氰基亚甲基产物3形成。 - ë自1-合成E. 4在λ照射最大532 nm产生了回复到3- E的原始浅黄色的信号。

  DOI：

  10.1002/jhet.5570370606
• 作为产物：
  描述：

  3-(Dicyclopropylmethylidene)-4-[1-(2,5-dimethylfuran-3-yl)ethylidene]oxolane-2,5-dione 以 吡啶 为溶剂， 反应 4.0h， 以0.95 g的产率得到(E)-dicyclopropylidene(2,5-dimethyl-3-furyl)ethylidenesuccinic anhydride
  参考文献：
  名称：

  A convenient method for conversion of the Z-isomer to the E-isomer from a mixture containing both isomers of fulgides

  摘要：

  A new method for the conversion of the Z-isomer of unsymmetrical substituted bis-methylenesuccinic anhydrides, 'fulgides', to their geometrical E-isomers was achieved by heating the Z-isomer under reflux or a mixture of both isomers in pyridine to give the E-isomer in near quantitative yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01514-9

文献信息

• Photochromic heteroaromatic thiofulgides and dimethoxybutanoic acid lactones
  作者：Matthew Badland、Alison Cleeves、Harry G. Heller、David S. Hughes、Michael B. Hursthouse

  DOI：10.1039/b002033h

  日期：——

  Thiofulgides 1, (X = S) cyclise on irradiation with UV light to form thermally stable photochromes 2, (X = S) that absorb at much longer wavelengths than photochromes 2, (X = O), formed from corresponding fulgides 1, (X = O), reverse reactions occur on exposure to white light; photochromic thiofulgides are prepared by reaction of fulgides with sodium hydrosulfide in hot toluene and photochromic lactones 9 and 12 are prepared by reaction of fulgides with sodium hydrosulfide in cold methanol followed by cyclisation with a carbodiimide.

  硫代氟化物1（X = S）在紫外线照射下环化，形成热稳定的光致变色体2（X = S），其吸收波长比光致变色体2（X = O）长得多，光致变色体2（X = O）由相应的硫代氟化物1（X = O）形成，在白光照射下发生逆反应；光致变色硫代氟化物通过氟化物与热甲苯中的氢化硫钠反应制备，光致变色内酯9和12通过氟化物与冷甲醇中的氢化硫钠反应制备，随后与碳二亚胺环化。
• On the spectroscopic analyses of (E)-3-(dicyclopropyl methylene)-dihydro-4-[1-(2,5 dimethylfuran-3-yl) ethylidene]furan-2,5-dione
  作者：M. Ibrahim、A.A. El-Barbary、M.M. El-Nahass、M.A. Kamel、M.A.M. El-Mansy、A.M. Asiri

  DOI：10.1016/j.saa.2011.11.039

  日期：2012.2

  In this work, a combined experimental and theoretical study on molecular structure and vibrational frequencies of (E)-3-(dicyclopropyl methylene)-dihydro-4-[1-(2,5 dimethylfuran-3-yl) ethylidene] furan-2,5-dione [DCPF] were reported. The FT-IR spectra of DCPF isomers are recorded in the solid phase. The equilibrium geometries, harmonic vibrational frequencies, thermo-chemical parameters, total dipole

  在这项工作中，对（E）-3-（二环丙基亚甲基）-二氢-4- [1-（2,5二甲基呋喃-3-基）亚乙基]呋喃-2的分子结构和振动频率进行组合的实验和理论研究。报道了5-5-二酮[DCPF]。DCPF异构体的FT-IR光谱记录在固相中。根据密度泛函理论DFT / B3LYP，使用6-311G（d，p）基集，计算了平衡几何形状，谐波振动频率，热化学参数，总偶极矩和HOMO-LUMO能量。结果表明，标度频率与实验值非常吻合。对于E和C异构体，DCPF异构体的HOMOs和LUMOs能量分别为3.8和2.7eV。
• Thermally stable fatigue resistant near infrared active photochromic compounds, exemplified by 6-amino-7-cyano-3-(dicyclopropylmethylene)-4-(2,5-dimethyl-3-furyl)-benzofuran-2(3H)-one
  作者：Harry G. Heller、David S. Hughes、Michael B. Hursthouse、Neil G. Rowles

  DOI：10.1039/b003496g

  日期：——

  The title pale yellow photochromic compound 11b in toluene, on irradiation at 366 nm, cyclises to the thermally stable infrared active blue–green photochrome, 8-amino-7-cyano-4,4-dicyclopropyl-3a,4-dihydro-6-hydroxy-2,3a-dimethylnaph tho[2,1-b]furan-5,6-carbolactone, 12b which has a λmax value of 720 nm for its broad long wavelength absorption band.

  淡黄色光致变色化合物 11b 在甲苯中，经 366 纳米波长照射后，循环生成热稳定的红外活性蓝绿色光致变色色素 8-氨基-7-氰基-4,4-二环丙基-3a,4-二氢-6-羟基-2,3a-二甲基萘并[2,1-b]呋喃-5,6-甲内酯 12b，其宽长波长吸收带的λmax 值为 720 纳米波长。
• Spectral Studies on Charge Transfer Complexes Between (<i>E</i>)-Dicyclopropylmethylene(2,5-dimethyl-3-furylethyldiene)succinic Anhydride and π-Acceptors
  作者：Shar S. Al-Shihry

  DOI：10.1080/15421400590946325

  日期：2005.5.1

  Charge transfer (CT) complexes formed through the reaction of (E)-dicyclopropyl-methylene(2,5-dimethyl-3-furylethyldiene)succinic anhydride as a donor and some pi-acceptors namely, 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), p-chloranil (CHL) and chloranilic acid (CNA) were prepared. The structure of the synthesized complexes were characterized by elemental analysis, IR and electronic absorption spectra. Spectral characteristics of the CT complexes were discussed in terms of donor molecular structure and pi-acceptor electron affinity. Ionization potential of the donor was estimated from the CT transition energies of its complexes.
• Photochromic and fluorescence properties of coumarin fulgimides
  作者：Khamis Nassor ALLY、Leyla ÖZTÜRK、Mahmut KÖSE

  DOI：10.3906/kim-2003-31

  日期：——

  Four new fulgimides possessing a fluorescent coumarin unit were synthesized from the corresponding fulgides, and their photochromic as well as fluorescence properties were investigated. The open-ring forms of coumarin fulgimides were found to exhibit fluorescence in the visible region. Upon exposure to UV light, the fulgimides were transformed into the nonfluorescent closed-ring forms, which can be reverted to the initial fluorescent open-ring forms on exposure to visible light. The efficiency of quenching of fluorescence was as high as 95% at the photostationary state of UV irradiation.