4-{[5-oxo-2-phenyl-1,3-oxazol-4(5H)-ylidene]methyl}phenylacetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-{[5-oxo-2-phenyl-1,3-oxazol-4(5H)-ylidene]methyl}phenylacetate
• 英文别名: 4-(4-acetoxybenzylidene)-2-phenyl-1,3-oxazol-5-one；4-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)phenyl acetate；2-Phenyl-4-(p-acetoxy-benzyliden)-oxazol-5(4H)-on；2-phenyl-4-[[4-acetyloxyphenyl]methylene]-5(4H)-oxazolone；4-(4-acetoxy-benzylidene)-2-phenyl-4H-oxazol-5-one；4-(4-Acetoxy-benzyliden)-2-phenyl-4H-oxazol-5-on；[4-[(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]phenyl] acetate
• 化学式: C₁₈H₁₃NO₄
• mdl: MFCD00502411
• 分子量: 307.306
• InChiKey: QEUQVGFKMXYPPU-UHFFFAOYSA-N

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：

  4-{[5-oxo-2-phenyl-1,3-oxazol-4(5H)-ylidene]methyl}phenylacetate 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Synthesis and some pharmacological properties of N-benzoyl-α,β-dehydrodipeptides

  摘要：

  DOI：

  10.1007/bf00777134
• 作为产物：
  描述：

  马尿酸 、 4-乙酰氧基苯甲醛 在 sodium acetate 、 乙酸酐 、 PPA 作用下， 反应 2.0h， 以56%的产率得到4-{[5-oxo-2-phenyl-1,3-oxazol-4(5H)-ylidene]methyl}phenylacetate
  参考文献：
  名称：

  Oxazolones: New tyrosinase inhibitors; synthesis and their structure–activity relationships

  摘要：

  The tyrosinase inhibitory potential of seventeen synthesized oxazolone derivatives has been evaluated and their structure-activity relationships developed in the present work. All the synthesized derivatives, 3-19, demonstrated excellent in vitro tyrosinase inhibitory properties having IC50 values in the range of 1.23 +/- 0.37-17.73 +/- 2.69 mu M, whereas standard inhibitors L-mimosine and kojic acid have IC50 values 3.68 +/- 0.02 and 16.67 +/- 0.52 mu M,, respectively. Compounds 4-8 having IC50 values 3.11 +/- 0.95, 3.51 +/- 0.25, 3.23 +/- 0.66, 1.23 +/- 0.37, and 2.15 +/- 0.75, respectively, were found to be very active members of the series, even better than both the standard inhibitors. However, compounds 3, 9-11, 13, 14, 16, 17, and 19 were found to be better than kojic acid but not L-mimosine. (2-Methyl-4-[E,2Z)-3-phenyl-2-propenyliden]-1,3-oxazol-5(4H)-one (7) bearing a cinnamyol residue at C-4 of oxazolone moiety and an IC50 = 1.23 +/- 0.37 mu M was found to be the most active one among all tested compounds. These studies reveal that the substitution of functional group (s) at C-4 and C-2 positions plays a vital role in the activity of this series of compounds. It is concluded that compound 7 may act as a potential lead molecule to develop new drugs for the treatment of tyrosinase based disorders. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.014

文献信息

• Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore
  作者：Cheng-Yu Lee、Yun-Chung Chen、Hao-Chun Lin、Yuandong Jhong、Chih-Wei Chang、Ching-Hua Tsai、Chai-Lin Kao、Tun-Cheng Chien

  DOI：10.1016/j.tet.2012.04.102

  日期：2012.7

  A facile and effective synthesis for a wide variety of 4-arylidene-5-imidazolinone derivatives was developed. 4-Arylidene-5-oxazolinones were prepared by Erlenmeyer azlactone synthesis from N-acylglycines and arylaldehydes. The ring-opening reactions of the 4-arylidene-5-oxazolinones with primary amines afforded 2-acylamino-3-arylacrylamides in excellent yields. A new dehydrative cyclization of the

  开发了一种简便而有效的合成方法，用于合成各种4-亚芳基-5-咪唑啉酮衍生物。通过N-酰基甘氨酸和芳基醛的Erlenmeyer丁二酸内酯合成来制备4-亚芳基-5-恶唑啉酮。4-亚芳基-5-恶唑啉酮与伯胺的开环反应以优异的产率提供了2-酰基氨基-3-芳基丙烯酰胺。吡啶中2-酰基氨基-3-芳基丙烯酰胺在回流下的新脱水环化反应以良好的收率提供了相应的4-亚芳基-5-咪唑啉酮。
• An efficient and concise method to synthesize locked GFP chromophore analogues
  作者：Soumit Chatterjee、Peter Karuso

  DOI：10.1016/j.tetlet.2016.10.021

  日期：2016.11

  A series of GFP analogues, which are fluorescent in the solid state at room temperature, but weakly fluorescent in solution, have been synthesized via an oxazolone formation process that involves a condensation reaction in the presence of a Lewis acid following a Knoevenagel condensation. A ring opened intermediate is formed which cyclizes readily upon heating to produce the imidazolinone. This method

  已经通过恶唑酮形成过程合成了一系列GFP类似物，其在室温下在固态下是荧光的，但是在溶液中却是弱荧光的，该过程涉及在Knoevenagel缩合之后在路易斯酸存在下的缩合反应。形成开环的中间体，该中间体在加热时容易环化以产生咪唑啉酮。与替代方法相比，此方法更快，更简单并且产生更高的产量。一些类似物代表锁定的GFP衍生物，其中环外单键旋转已停止。即使停止单键旋转后，荧光强度仍然很弱，这表明构象限制没有得到有效控制，而双键旋转仅是主要的非辐射途径。
• Synthesis of phosphorylated dehydrotyrosine-containing tripeptides from 5-amino-2-aminoalkyl-1,3-oxazole-4-phosphonic acids derivatives
  作者：E. I. Lukashuk、E. R. Abdurakhmanova、K. M. Kondratyuk、A. V. Golovchenko、V. S. Brovarets

  DOI：10.1134/s1070363215010120

  日期：2015.1

  5-amino-2-aminoalkyl-1,3-oxazole with 4-(4-acetoxybenzylidene)-2-phenyl-1,3-oxazol-5-one resulted in the formation of new 1,3-oxazole derivatives. The latter undergo 1,3-oxazole ring opening to give phosphorylated tripeptides with a dehydrotyrosine fragment.

  5-氨基-2-氨基烷基-1,3-恶唑的4-磷酸化衍生物与4-（4-乙酰氧基亚苄基）-2-苯基-1,3-恶唑-5-酮的相互作用导致形成新的1， 3-恶唑衍生物。后者经历1，3-恶唑开环，得到具有脱氢酪氨酸片段的磷酸化三肽。
• Karade; Shirodkar; Dhoot, Journal of Chemical Research, 2005, # 1, p. 46 - 47
  作者：Karade、Shirodkar、Dhoot、Waghmare

  DOI：——

  日期：——
• Mauthner, Justus Liebigs Annalen der Chemie, 1909, vol. 370, p. 374
  作者：Mauthner

  DOI：——

  日期：——