(Z)-4-dicyclopropylmethylene-3-[1-(2,5-dimethylfuryl)ethylidene]tetrahydrofuran-2,5-dione | 166194-21-4

• 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: (Z)-4-dicyclopropylmethylene-3-[1-(2,5-dimethylfuryl)ethylidene]tetrahydrofuran-2,5-dione
• 英文别名: (Z)-dicyclopropylidene(2,5-dimethyl-3-furyl)ethylidenesuccinic anhydride；(Z)-3-[1-(2,5-Dimethyl-3-furyl)ethylidene]-4-(dicyclopropylmethylene)tetrahydrofuran-2,5-dione；(4Z)-3-(dicyclopropylmethylidene)-4-[1-(2,5-dimethylfuran-3-yl)ethylidene]oxolane-2,5-dione
• CAS: 166194-21-4
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: FZKPXLWLLPOXPG-GDNBJRDFSA-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：

  (Z)-4-dicyclopropylmethylene-3-[1-(2,5-dimethylfuryl)ethylidene]tetrahydrofuran-2,5-dione 在 sodium hydrogensulfide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (Z)-4-dicyclopropylmethylene[1-(2,5-dimethyl-3-furyl)ethylidene]thiosuccinic anhydride
  参考文献：
  名称：

  Photochromic heteroaromatic thiofulgides and dimethoxybutanoic acid lactones

  摘要：

  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。

  DOI：

  10.1039/b002033h
• 作为产物：
  描述：

  dimethyldicyclopropylmethylene succinate 、 3-乙酰基-2,5-二甲基呋喃 在 potassium tert-butylate 、 氢氧化钾 作用下， 以 甲苯 、 乙醇 为溶剂， 反应 3.0h， 生成 (Z)-4-dicyclopropylmethylene-3-[1-(2,5-dimethylfuryl)ethylidene]tetrahydrofuran-2,5-dione 、 (E)-dicyclopropylidene(2,5-dimethyl-3-furyl)ethylidenesuccinic anhydride
  参考文献：
  名称：

  Spectral Studies on Charge Transfer Complexes Between (E)-Dicyclopropylmethylene(2,5-dimethyl-3-furylethyldiene)succinic Anhydride and π-Acceptors

  摘要：

  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.

  DOI：

  10.1080/15421400590946325

文献信息

• Photochromic fulgides: Transformation of the non-photochromic (Z)-isomer of a fulgide into a highly photochromic (<i>E</i>)-isomer<i>via</i>structural modification involving enhanced conjugation
  作者：Zhiyuan Sun、Ramachandra S. Hosmane、Maher Tadros

  DOI：10.1002/jhet.5570370606

  日期：2000.11

  The non-photochromic fulgide (1-Z) has been successfully converted into the highly photochromic (3-Z) analogue. A dicyanomethylene group was introduced at the 5-position of 1-Z in order to enhance the latter's conjugation properties that would facilitate the photochemical Z→E isomerization process. The irradiation of the product 3-Z with a UV light at λmax 350 nm formed a bluish green solution which

  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。
• 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。
• A new class of photochromic compounds exemplified by E-5-dicyanomethylene-4-(dialkyl and dicycloalkyl)methylene[1-(2,5-methyl-3-furyl) and (2-methyl-5-phenyl-3-thienyl)ethylidene]tetrahydrofuran-2-ones
  作者：Harry G. Heller、David S. Hughes、Michael B. Hursthouse、Kevin V. S. Kon

  DOI：10.1039/c39940002713

  日期：——

  The title photochromic compounds 4 photocyclise to thermally stable blue and infrared active 7-dicyanomethylene-5-oxo-5,7,8,8a-tetrahydro-2-substituted-4,8a-dimethylfuro[33,4-f]benzofurans or benzothiophenes 5 which absorb at longer wavelengths (>100 nm) than the photocyclised compounds 2 from the corresponding photochromic fulgides 1.

  标题光致变色化合物 4 经光循环生成热稳定的蓝色和红外活性 7-二氰亚甲基-5-氧代-5,7,8,8a-四氢-2-取代-4,8a-二甲基呋喃并[33,4-f]苯并呋喃或苯并噻吩 5，其吸收波长（大于 100 纳米）比相应光致变色富集物 1 光循环生成的化合物 2 更长。
• A convenient method for conversion of the Z-isomer to the E-isomer from a mixture containing both isomers of fulgides
  作者：Abdullah Mohamed Asiri

  DOI：10.1016/s0040-4039(02)01514-9

  日期：2002.9

  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.