3,4-bis(2,5-dimethylthiophen-3-yl)furan-2(5H)-one | 876928-85-7

• 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: 3,4-bis(2,5-dimethylthiophen-3-yl)furan-2(5H)-one
• 英文别名: 3,4-Bis(2,5-dimethylthiophen-3-yl)furan-2(5h)-one；3,4-bis(2,5-dimethylthiophen-3-yl)-2H-furan-5-one
• CAS: 876928-85-7
• 化学式: C₁₆H₁₆O₂S₂
• 分子量: 304.434
• InChiKey: CDPLXVYZCCUASC-UHFFFAOYSA-N

物化性质

• 熔点：
  153-155 °C
• 沸点：
  490.1±45.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-bis(2,5-dimethylthiophen-3-yl)furan-2(5H)-one 在 氧气 、 potassium carbonate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 N-[3,4-bis(2,5-dimethyl-3-thienyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl]thiourea
  参考文献：
  名称：

  Synthesis and photochromic properties of dithienylmaleimides with sulfur-containing fragments

  摘要：

  合成了多种含硫二噻吩马来酰亚胺衍生物。对所得化合物的光谱和动力学特性进行了研究，结果表明合成的所有二噻吩乙烯均具有光致变色性能。

  DOI：

  10.1007/s11172-012-0295-z
• 作为产物：
  描述：

  2,5-二甲基噻吩 在 三氯化铝 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3,4-bis(2,5-dimethylthiophen-3-yl)furan-2(5H)-one
  参考文献：
  名称：

  Synthesis and properties of dihetaryl-substituted furanones. Synthesis of photochromic dithienylethenes containing a furanone bridging fragment

  摘要：

  The reaction of 2,5-dimethylthiophen-3-ylacetic acid with 2,5-dimethylthiophen-3-ylacetyl chloride gave 3,4-bis(2,5-dimethylthiophen-3-yl)furan-2(5H)-one which was converted into a series of 5-methylidene and 5-arylmethylidene derivatives.

  DOI：

  10.1134/s1070428006120104

文献信息

• Thermally irreversible organic photochromic compounds for optical memory
  作者：V. A. Barachevsky、Yu. P. Strokach、Yu. A. Puankov、M. M. Krayushkin

  DOI：10.1002/poc.1191

  日期：2007.11

  some photochromic compounds (58 diarylethenes and 9 fulgimides), the results of our spectral and kinetic studies are presented. Aiming at targeted synthesis of new photochromic compounds, the structure – photochromic behavior relationship (SPBR) for the synthesized compounds has been analyzed. The perspectives for application of these compounds in development of recording media for use in optical memory

  对于某些光致变色化合物（58个双芳硫醚和9个全黄酰亚胺），我们给出了光谱和动力学研究的结果。为了有针对性地合成新的光致变色化合物，已经分析了合成化合物的结构-光致变色行为关系（SPBR）。概述了这些化合物在开发用于光学存储设备的记录介质中的应用前景。版权所有©2007 John Wiley＆Sons，Ltd.
• Photochromic organic compounds for optical memory
  作者：V. A. Barachevsky、M. M. Krayushkin

  DOI：10.1007/s11172-008-0124-6

  日期：2008.4

  For the purpose of target syntheses of new photochromic compounds, a relationship between the structure and properties of a series of the known thermally irreversible photochromes was analyzed using the spectral kinetic data obtained by the authors.

  为了合成新的光致变色化合物，使用作者获得的光谱动力学数据分析了一系列已知的热不可逆光致变色化合物的结构和性质之间的关系。
• Quantitative study of photochromic transformations of diarylethene derivatives with either perhydrocyclopentene or oxazolone or lactone units
  作者：J.-C. Micheau、C. Coudret、O.I. Kobeleva、V.A. Barachevsky、V.N. Yarovenko、S.N. Ivanov、B.V. Lichitsky、M.M. Krayushkin

  DOI：10.1016/j.dyepig.2014.02.013

  日期：2014.7

  This work is devoted to the determination of ring-closure and ring-opening quantum yield values of 18 thermally irreversible photochromic diarylethene derivatives. Three classes have been systematically investigated. They have been obtained (i) by changing the bridging ring that stabilizes the central ethenic double bond in the cis configuration from perhydrocyclopentene, oxazolone and lactones, and (ii) by varying the lateral aryl moieties from thiophene, benzothiophene and thiazoles. Numerical modeling of UV/visible absorption vs time kinetic curves recorded under continuous monochromatic irradiation in combination with chemical actinometry was employed to determine the photo-cyclisation and cycloreversion quantum yields together with the molar absorption coefficient of the closed form. Structure-properties diagrams obtained by plotting lambda(A) vs lambda(B), epsilon(A) VS epsilon(B) and phi(AB) VS phi(BA) Visualize all the structural effects helping the evaluation of these compounds as possible photoswitches or high-density optical recording materials. (C) 2014 Elsevier Ltd. All rights reserved.
• Photochromism of Thienyl-Containing Dihetarylethenes with Five-Membered Cyclic Bridges
  作者：V. A. Barachevsky、Yu. P. Strokach、M. M. Krayushkin

  DOI：10.1080/15421400590946352

  日期：2005.5.1

  Spectral-kinetic characteristics of a number of new photochromic dihetaryethenes with different five-membered cyclic bridges are measured and discussed. It was shown that these characteristics depend on a bridge structure as well as a nature of substituents in the thienyl fragments.
• Synthesis and properties of dihetaryl-substituted furanones. Synthesis of photochromic dithienylethenes containing a furanone bridging fragment
  作者：M. M. Krayushkin、D. V. Pashchenko、B. V. Lichitskii、T. M. Valova、Yu. P. Strokach、V. A. Barachevskii

  DOI：10.1134/s1070428006120104

  日期：2006.12

  The reaction of 2,5-dimethylthiophen-3-ylacetic acid with 2,5-dimethylthiophen-3-ylacetyl chloride gave 3,4-bis(2,5-dimethylthiophen-3-yl)furan-2(5H)-one which was converted into a series of 5-methylidene and 5-arylmethylidene derivatives.