3-[Z-α-(2,5-dimethyl-3-thienyl)ethylidene]-4-isopropylidene-2,5-furanidinedione | 59000-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-[Z-α-(2,5-dimethyl-3-thienyl)ethylidene]-4-isopropylidene-2,5-furanidinedione
• 英文别名: (Z)-1-(2,5-dimethyl-3-thienyl)ethylidene(isopropylidene)succinic anhydride；(Z)-2-<α-(2,5-dimethyl-3-thienyl)ethylidene>-3-isopropylidenesuccinic anhydride；(Z)-3-[1-(2,5-Dimethyl-3-thienylfuryl)ethylidene]-4-isopropylidenetetrahydrofurandione；fulgide；3-(Z)-[1-(2,5-dimethyl-3-thienyl)ethylidene]-4-isopropylidenetetrahydrofuran-2,5-dione；(3Z)-3-[1-(2,5-dimethyl-3-thienyl)ethylidene-4-isopropylidene]-2,5-furandione；(3Z)-3-[1-(2,5-dimethyl-3-thienyl)ethylidene]-4-isopropylidenefuran-2,5-dione；(3z)-3-[1-(2,5-Dimethyl-3-thienyl)ethylidene]-4-isopropylidene-2,5-furandione；(3Z)-3-[1-(2,5-dimethylthiophen-3-yl)ethylidene]-4-propan-2-ylideneoxolane-2,5-dione
• CAS: 59000-90-7
• 化学式: C₁₅H₁₆O₃S
• 分子量: 276.356
• InChiKey: AQRCMKAWFZWRIR-LCYFTJDESA-N

物化性质

• 熔点：
  155-156 °C(Solv: chloroform (67-66-3); ligroine (8032-32-4))
• 沸点：
  411.5±45.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[Z-α-(2,5-dimethyl-3-thienyl)ethylidene]-4-isopropylidene-2,5-furanidinedione 在 二乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 2-{4-[1-(2,5-Dimethyl-thiophen-3-yl)-eth-(E)-ylidene]-3-isopropylidene-5-oxo-dihydro-furan-2-ylidene}-malononitrile
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.1039/b003496g
• 作为产物：
  描述：

  2,5-二甲基噻吩 在 potassium tert-butylate 、 四氯化锡 、 N,N'-羰基二咪唑 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 18.5h， 生成 3-[Z-α-(2,5-dimethyl-3-thienyl)ethylidene]-4-isopropylidene-2,5-furanidinedione
  参考文献：
  名称：

  通过（3 Z）-3- [1-（2,5-二甲基-3-噻吩基）-亚乙基] -4-异亚丙基-2,5-呋喃二酮与芳族二胺的缩合反应合成光致变色双富马酰亚胺

  摘要：

  通过（3Z）-3- [1-（2-（2,5-二甲基-3-噻吩基）亚乙基] -4-异亚丙基-2,5的缩合反应获得在一个分子中具有两个fulgimide片段的噻吩衍生物的首个代表-呋喃二酮与芳香族二胺。已经研究了获得的化合物的光致变色性质，并且研究了连接两个富马来酰亚胺片段的间隔基对这些化合物的光致变色和光致脱色反应速率的影响。

  DOI：

  10.1007/s10593-010-0589-8

文献信息

• Synthesis and spectral-kinetic investigation of fulgimide-based photochromic autocomplexes of the dinitroquinoline series
  作者：I. G. Ilyina、V. V. Mel’nikov、S. I. Luyksaar、M. M. Krayushkin、Yu. A. P’yankov、V. A. Barachevsky、I. V. Fedyanin

  DOI：10.1007/s11172-008-0187-4

  日期：2008.7

  Two new hybrid compounds, which belong to autocomplexes of the dinitroquinoline series and contain an NH spacer and fragments of photochromic fulgimides as donor components, were synthesized. These autocomplexes were used as ligands in the synthesis of cobalt-containing metal chelates. The spectral-kinetic study revealed that these compounds exhibit photochromism. The introduction of photochromic fulgimide moieties into the autocomplexes has no substantial effect on the spectral properties of the latter but influences the kinetics of photochromic transformations by decreasing their efficiency. Chelate complexes of the hybrid compounds with cobalt ions are characterized by the lowest efficiency of photochromic transformations due to a decrease in the intensity of activating radiation as a result of its absorption by the dinitroquinoline moieties, which are not conjugated with fragments of photochromic compounds.

  合成了两种新的杂合化合物，这些化合物属于二硝基喹啉系列的自复合物，包含一个NH间隔和光致变色的富尔基米德片段作为供体组分。这些自复合物被用作配体，合成了含钴的金属螯合物。光谱动力学研究表明，这些化合物表现出光致变色特性。将光致变色富尔基米德基团引入自复合物对后者的光谱性质没有实质性影响，但通过降低其效率影响了光致变色转变的动力学。与钴离子的杂合化合物的螯合络合物由于其吸收二硝基喹啉部分的激活辐射而导致激发光强度降低，表现出最低效的光致变色转变效率，而这些部分与光致变色化合物的片段并不共轭。
• Syntheses and UV/Vis Properties of Amino-Functionalized Fulgimides
  作者：Bernhard Otto、Karola Rück-Braun

  DOI：10.1002/ejoc.200200680

  日期：2003.7

  Functionalized fulgimides are regarded as a promising class of photochromic compounds for modulating the structure and function of biomolecules. A new synthetic route to fulgimides bearing amino-functionalized substituents at the imide nitrogen atom has been developed. The synthesis of the fulgimides has been achieved by base-catalyzed cyclization of phenacyl esters of the succinamic acids derived

  功能化的 fulgimides 被认为是一类很有前途的光致变色化合物，用于调节生物分子的结构和功能。已经开发了在酰亚胺氮原子上带有氨基官能化取代基的 fulgimides 的新合成路线。fulgimides 的合成是通过碱催化环化琥珀酰胺酸的苯甲酸酯和 N-Boc 保护的烷基和芳基取代的二胺与三乙胺或叔丁基锂而实现的。已经研究了这些新化合物的紫外/可见光谱数据和光致变色特性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Amino-substituted spirooxazine and fulgimide for the nanostructurized photochromic systems
  作者：E. A. Karpuzova、A. I. Shienok、L. S. Kol’tsova、N. L. Zaichenko、S. I. Luiksaar、M. M. Krayushkin、V. A. Barachevsky、G. V. Popova、M. F. Bobrov

  DOI：10.1007/s11172-010-0246-5

  日期：2010.7

  Comparative spectral kinetic studies of the photochromic properties of a novel N-aminofulgimide and the previously synthesized aminospirooxazine intended for the synthesis of organic-inorganic photochromic systems based on cyclotriphosphazene were performed. The results from the spectral kinetic studies evidence the fundamental suitability of these compounds for design of the multifunctional photochromic systems based on cyclotriphosphazene. Computer molecular models of aminospirooxazine and N-aminofulgimide were developed and optimization of geometric parameters was performed by the semiempirical quantum chemical method AM1.

  研究人员对一种新型 N-氨基富尔基酰亚胺和之前合成的氨基螺噁嗪的光致变色特性进行了光谱动力学比较研究，这些化合物旨在合成基于环三磷嗪的有机-无机光致变色系统。光谱动力学研究结果表明，这些化合物非常适合设计基于环三唑磷的多功能光致变色系统。通过半经验量子化学方法 AM1，建立了氨基螺噁嗪和 N-氨基富尔格米德的计算机分子模型，并对几何参数进行了优化。
• N,N’-Carbonyldiimidazole as a reagent of choice for the synthesis of thienyl-substituted pyrrolidine-2,5-diones
  作者：Mikhail M. Krayushkin、Felix M. Stoyanovich、Sergei V. Shorunov

  DOI：10.1070/mc2003v013n04abeh001761

  日期：2003.1

  o-3-[Z-α-(2,5-dimethyl-3-thienyl)ethylidene]-4-isopropylidenepyrrolidine-2,5-dione was prepared in 80% yield from the corresponding isomeric hydrazidic acids using N,N'-carbonyldiimidazole, whereas a number of other cyclisation reagents were ineffective.

  使用N，以80％的产率由相应的异构肼基酸制备N-叔丁氧基羰基氨基-3- [Z-α-（2,5-二甲基-3-噻吩基）亚乙基] -4-异亚丙基吡咯烷-2,5-二酮。 N，-羰基二咪唑，而许多其他环化试剂无效。
• Glaze, Alan P.; Harris, Stuart A.; Heller, Harry G., Journal of the Chemical Society. Perkin transactions I, 1985, p. 957 - 962
  作者：Glaze, Alan P.、Harris, Stuart A.、Heller, Harry G.、Johncock, William、Oliver, Stephen N.、et al.

  DOI：——

  日期：——