4,5-bis(2,5-dimethyl-3-thienyl)-3-methyl-1,3-oxazole-2(3H)-one | 514814-24-5

• 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: 4,5-bis(2,5-dimethyl-3-thienyl)-3-methyl-1,3-oxazole-2(3H)-one
• 英文别名: 4,5-Bis(2,5-dimethylthiophen-3-yl)-3-methyl-1,3-oxazol-2(3H)-one；4,5-bis(2,5-dimethylthiophen-3-yl)-3-methyl-1,3-oxazol-2-one
• CAS: 514814-24-5
• 化学式: C₁₆H₁₇NO₂S₂
• 分子量: 319.448
• InChiKey: QTQLGZJDZIFUGC-UHFFFAOYSA-N

物化性质

• 沸点：
  441.3±55.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 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：
  86
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-bis(2,5-dimethyl-3-thienyl)-3-methyl-1,3-oxazole-2(3H)-one 以 甲苯 为溶剂， 生成 3,5,6a,6b,8-Pentamethyl-6a,6b-dihydro-3H-1-oxa-6,7-dithia-3-aza-trinden-2-one
  参考文献：
  名称：

  用于光学存储器的热不可逆有机光致变色化合物

  摘要：

  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.

  DOI：

  10.1002/poc.1191
• 作为产物：
  描述：

  1,2-双(2,5-二甲基-3-噻吩基)-2-羟基乙酮 以 乙醇 、 苯 为溶剂， 生成 4,5-bis(2,5-dimethyl-3-thienyl)-3-methyl-1,3-oxazole-2(3H)-one
  参考文献：
  名称：

  摘要：

  Procedures were developed for the synthesis of substituted bis(2,5-dimethyl-3-thienyl)ethenes containing the imidazol-2-one, 1,3-dioxol-2-one, or 1,3-oxazol-2-one fragments as ethene bridges. These compounds were demonstrated to exhibit the photochromic properties. The cyclic forms of some imidazolone and oxazolone photochromes possess high thermal stability. The structure of photochromic 4,5-bis(4-acetyl-2,5-dimethyl-3-thienyl)-3-methyl-2,3-dihydro-1,3-oxazol-2-one was established by X-ray diffraction analysis. The molecule adopts an anti-parallel conformation similar to that of perfluorocyclopentene-bridged dithienylethenes.

  DOI：

  10.1023/a:1021367909022

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。
• Synthesis and photochromic properties of 1,2-dihetarylethenes with 1,3-dioxole- and 1,3-oxazole-2-thione bridges
  作者：S. N. Ivanov、M. M. Krayushkin、B. V. Lichitsky、A. A. Dudinov、A. Yu. Martynkin

  DOI：10.1007/s11172-005-0405-2

  日期：2005.5

  Methods for the synthesis of substituted bis(2,5-dimethyl-3-thienyl)ethenes with 1,3-dioxole- and 1,3-oxazole-2-thione fragments as ethene bridges were developed. These compounds exhibit photochromic properties.

  开发了以 1,3- 二氧杂环戊烯和 1,3- 恶唑-2-硫酮片段为乙烯桥的取代双（2,5-二甲基-3-噻吩基）乙烯的合成方法。这些化合物具有光致变色特性。
• 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.
• 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.