4,5-bis(4-acetyl-2,5-dimethyl-3-thienyl)-3-methyloxazol-2(3H)-one | 514814-31-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-bis(4-acetyl-2,5-dimethyl-3-thienyl)-3-methyloxazol-2(3H)-one
• 英文别名: 4,5-bis(4-acetyl-2,5-dimethyl-3-thienyl)-3-methyl-2,3-dihydro-1,3-oxazol-2-one；4,5-bis(4-acetyl-2,5-dimethylthiophen-3-yl)-3-methyl-1,3-oxazol-2-one
• CAS: 514814-31-4
• 化学式: C₂₀H₂₁NO₄S₂
• 分子量: 403.523
• InChiKey: AJMHQPVADHUXLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-bis(4-acetyl-2,5-dimethyl-3-thienyl)-3-methyloxazol-2(3H)-one 以 乙腈 为溶剂， 生成 4,9-Diacetyl-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：

  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
• 作为产物：
  描述：

  1,2-双(2,5-二甲基-3-噻吩基)-2-羟基乙酮 在 三氯化铝 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 6.0h， 生成 4,5-bis(4-acetyl-2,5-dimethyl-3-thienyl)-3-methyloxazol-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

• 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.