(Z)-4-o-acetoxybenzylidene-2-phenyl-4,5-dihydrooxazol-5-one | 35175-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (Z)-4-o-acetoxybenzylidene-2-phenyl-4,5-dihydrooxazol-5-one
• 英文别名: 2-Phenyl-4-[(Z)-2-acetoxybenzylidene]-4,5-dihydrooxazole-5-one；[2-[(Z)-(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]phenyl] acetate
• CAS: 35175-74-7
• 化学式: C₁₈H₁₃NO₄
• 分子量: 307.306
• InChiKey: CKVAALAFCQXIGK-PTNGSMBKSA-N

物化性质

• 熔点：
  157-158 °C(Solv: chloroform (67-66-3))
• 沸点：
  457.0±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-4-o-acetoxybenzylidene-2-phenyl-4,5-dihydrooxazol-5-one 在 氢氧化钾 、 硫酸 作用下， 以 水 为溶剂， 反应 0.67h， 生成 (Z)-2-benzoylamino-3-(2-hydroxyphenyl)acrylic acid methyl ester
  参考文献：
  名称：

  Cornforth, Sir John; Ming-hui, Du, Journal of the Chemical Society. Perkin transactions I, 1991, p. 2183 - 2187

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯基-5-噁唑酮 在 sodium hydroxide 、 硫酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 3.17h， 生成 (Z)-4-o-acetoxybenzylidene-2-phenyl-4,5-dihydrooxazol-5-one
  参考文献：
  名称：

  Cornforth, Sir John; Ming-hui, Du, Journal of the Chemical Society. Perkin transactions I, 1991, p. 2183 - 2187

  摘要：

  DOI：

文献信息

• Alcohol Uncaging with Fluorescence Reporting: Evaluation of <i>o</i>-Acetoxyphenyl Methyloxazolone Precursors
  作者：Nathalie Gagey、Matthieu Emond、Pierre Neveu、Chouaha Benbrahim、Bernard Goetz、Isabelle Aujard、Jean-Bernard Baudin、Ludovic Jullien

  DOI：10.1021/ol800284g

  日期：2008.6.1

  This paper evaluates a series of photolabile protecting groups with built-in fluorescence reporting. They rely on readily available o-acetoxyphenyl methyloxazolones as activated precursors. Alcohol substrates are easily caged. The resulting photoactivable esters exhibit large one- and two-photon uncaging cross sections. The alcohol substrates are quantitatively released in a 1:1 molar ratio with a

  本文利用内置的荧光报告评估了一系列对光不稳定的保护基。他们依靠现成的邻乙酰氧基苯基甲基恶唑酮作为活化的前体。酒精基质很容易笼罩。所得的可光活化的酯表现出大的单光子和双光子解开截面。醇底物与强荧光香豆素副产物以1：1摩尔比定量释放，该香豆素副产物用作定量底物递送的报告分子。
• Study on dry-media microwave azalactone synthesis on different supported KF catalysts: influence of textural and acid–base properties of supports
  作者：Felipa M. Bautista、Juan M. Campelo、Angel García、Diego Luna、José M. Marinas、Antonio A. Romero

  DOI：10.1039/b109413k

  日期：2002.1.23

  Twenty-five inorganic solids studied as supports for KF were screened with respect to the synthesis of the azalactone obtained by dry-media condensation of p-hydroxybenzaldehyde with hippuric acid in acetic anhydride (1 ∶ 1 ∶ 4, molar ratio), in 3 g of 10 wt% KF support catalysts. The results obtained indicate that there was a number of supported KF catalysts with conversions higher than or comparable to that obtained by the classical Erlenmeyer method of azalactone synthesis. Furthermore, not only were there very important differences in the catalytic behavior of different KF support systems, but also these differences are closely related to the procedure used in the reaction heating. In this respect, the well-documented KF–Al2O3 was the best catalyst when reactions were conducted under conventional heating. However, when reactions were carried out in a domestic microwave oven, KF supported on AlPO4, TiO2 or Zn3(PO4)2 were better catalysts than KF–Al2O3. The importance of the textural and acid–base properties of solid inorganic supports was also demonstrated with respect to the catalytic behavior of supported KF catalysts. Finally, results obtained in the synthesis of thirteen different azalactones, lead us strongly to recommend the procedure using microwave irradiation and KF–AlPO4, over classical heating with KF–Al2O3. The advantages are good yields, easier work-up, a significant decrease in reaction times, and easy re-use of catalysts when operated in dry-media, especially by use of a domestic microwave oven.

  筛选了25种无机固体作为KF的载体，研究了它们在醋酸酐中与对羟基苯甲醛和马尿酸进行干介质缩合合成的Azalactone的效率（1 : 1 : 4的摩尔比），采用3克的10 wt% KF载体催化剂。结果表明，存在一些KF载体催化剂的转化率高于或媲美经典的Erlenmeyer法合成Azalactone的转化率。此外，不同KF载体系统的催化行为存在非常重要的差异，这些差异与反应加热的程序密切相关。在这方面，经过充分文献证明的KF–Al2O3在常规加热下的反应中是最佳催化剂。然而，当反应在家庭微波炉中进行时，载于AlPO4、TiO2或Zn3(PO4)2上的KF表现出优于KF–Al2O3的催化活性。固体无机载体的纹理和酸碱特性对支持KF催化剂的催化行为的重要性也得到了验证。最后，在合成十三种不同的Azalactone的研究结果使我们强烈推荐在微波辐射条件下使用KF–AlPO4的程序，而不是使用KF–Al2O3的经典加热方法。其优势在于产率良好、处理更简便、反应时间显著缩短，以及在干介质下操作时催化剂的易于重复使用，尤其是使用家庭微波炉时。
• Heller; Lauth, Chemische Berichte, 1919, vol. 52, p. 2297,2298
  作者：Heller、Lauth

  DOI：——

  日期：——
• Thiol-induced conversion of (Z)-4-o-acetoxybenzylidene-2-phenyl-4,5-dihydrooxazol-5-ones into 3-benzoylaminocoumarins
  作者：Arya K. Mukerjee、Kiran Joseph、Laxmi Rao

  DOI：10.1039/p19910002611

  日期：——

  Toluene-alpha-thiol induces cleavage of the 1,5-bond of (Z)-4-o-acetoxybenzylidene-2-phenyl-4,5-dihydrooxazol-5-ones in triethylamine-containing ethanol to give 3-benzoylaminocoumarins
• Ashare, Ram; Mukerjee, Arya K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 423 - 424
  作者：Ashare, Ram、Mukerjee, Arya K.

  DOI：——

  日期：——