(Z)-4-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)phenyl acetate | 71198-74-8

• 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-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)phenyl acetate
• 英文别名: 4,5-Dihydroxyoxazole-5-one, 4-[4-acetoxybenzylidene]-2-phenyl-；[4-[(Z)-(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]phenyl] acetate
• CAS: 71198-74-8
• 化学式: C₁₈H₁₃NO₄
• 分子量: 307.306
• InChiKey: QEUQVGFKMXYPPU-WJDWOHSUSA-N

物化性质

• 熔点：
  175-176 °C
• 沸点：
  455.4±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-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)phenyl acetate 在 potassium carbonate 、 甲胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.27h， 生成 1-methyl-2-phenyl-4-(1-phenylethylidene)-1H-imidazol-5(4H)-one
  参考文献：
  名称：

  [EN] DUAL EMISSION FLUORESCENT COMPOUNDS
  [FR] COMPOSÉS FLUORESCENTS À DOUBLE ÉMISSION

  摘要：

  该发明涉及一种双发射荧光化合物，包括适合在激发态发出第一波长的发射的色团；其中该化合物进一步包括一个或多个适合在形成激发态时诱导分子中的结构重排的基团，其中结构重排稳定至少第二波长的第二电磁发射，使得在室温下可观察到双发射。这种双发射可实现对样品的超灵敏比率定量。

  公开号：

  WO2017147646A1
• 作为产物：
  描述：

  苯甲酰氯 在 sodium acetate 、 乙酸酐 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.5h， 生成 (Z)-4-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)phenyl acetate
  参考文献：
  名称：

  巯基乙酸AC的简捷模块化合成。

  摘要：

  Deering等人从海洋细菌中分离出了新型的N-酰基脱氢酪氨酸类似物，称为拟海藻酸AC。在2016年。这些分子被证明具有酪氨酸酶抑制活性，因此是一组有吸引力的分子，需要进一步研究和优化。为此，已经设计并执行了简明且模块化的合成方法，以产生海藻酸AC和两种非天然类似物。该合成方法已经证实了海藻酸AC，更有效的合成类似物（IC50 = 65μM）的身份和抑制数据，并为进一步研究结构与活性之间的关系提供了一条途径，以优化这些分子。

  DOI：

  10.1021/acs.jnatprod.9b00028

文献信息

• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
  申请人：Chung Hae Young

  公开号：US20140023603A1

  公开（公告）日：2014-01-23

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白皮肤、抗氧化和PPAR活性的新化合物及其医疗用途，该化合物具有美白皮肤的活性，可抑制酪氨酸酶，因此适用于用于美白皮肤的药物组合物或化妆品；具有抗氧化活性，因此适用于预防和治疗皮肤老化；具有PPAR活性，特别是PPARα和PPARγ活性，因此适用于用于预防和治疗肥胖、代谢性疾病或心血管疾病的药物组合物或保健食品。
• Chemoselective Reduction of Azlactones Using Schwartz’s Reagent
  作者：Danielle L. J. Pinheiro、Eloah P. Ávila、Gabriel M. F. Batista、Giovanni W. Amarante

  DOI：10.1021/acs.joc.7b00820

  日期：2017.6.2

  Highly chemoselective addition of Schwartz’s reagent to widely available azlactones is described. This method allows the preparation of challenged functionalized α-amino aldehydes, in good to high isolated yields at room temperature, after only 2 min reaction. The presence of sensitive functionalities or electronic factors does not compromise the potential of the method. The use of an excess of the

  描述了将施瓦茨试剂高度化学选择性地添加到广泛可用的氮内酯中。该方法仅需反应2分钟，即可在室温下以良好或较高的分离产率制备受挑战的官能化α-氨基醛。敏感功能或电子因素的存在不会损害该方法的潜力。使用过量的还原剂以86％的收率得到了非常官能化的烯丙醇衍生物。
• 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。
• 피부미백, 항산화 및 ＰＰＡＲ 활성을 갖는 신규 화합물 및 이의 의학적 용도
  申请人：Pusan National University Industry-University Cooperation Foundation 부산대학교 산학협력단(220040044843) BRN ▼621-82-06530

  公开号：KR101677122B1

  公开（公告）日：2016-11-17

  본 발명은 피부미백, 항산화 및 PPAR 활성을 갖는 신규 화합물 및 이의 의학적 용도에 관한 것으로, 본 발명에 따른 화합물들은 티로시나아제를 억제하는 피부미백 활성을 지니므로 피부미백용 약학조성물 또는 화장품에 유용하게 사용될 수 있고, 항산화 활성을 지니므로 피부노화 등의 예방 또는 치료에 유용하게 사용될 수 있으며, 또한 PPAR 활성 특히, PPARα 및 PPARγ 활성을 지니므로 비만, 대사성 질환 또는 심혈관계 질환을 예방하고 치료하는 데에 유용한 약학조성물 또는 건강식품으로 사용될 수 있다.

  本发明涉及具有皮肤美白、抗氧化和PPAR活性的新化合物及其医学用途，根据本发明的化合物具有抑制酪氨酸酶的皮肤美白活性，因此可用于皮肤美白药物组合物或化妆品中，具有抗氧化活性，因此可用于预防或治疗皮肤老化等，另外，由于具有PPAR活性，特别是具有PPARα和PPARγ活性，因此可用作预防和治疗肥胖、代谢性疾病或心血管疾病的药物组合物或保健食品。
• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREOF
  申请人：Pusan National University Industry-University Cooperation Foundation

  公开号：US20160102065A1

  公开（公告）日：2016-04-14

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白、抗氧化和PPAR活性的新化合物及其医疗用途。该化合物具有抑制酪氨酸酶的美白活性，因此可用于美白药物组合物或化妆品产品；具有抗氧化活性，因此可用于预防和治疗皮肤老化；具有PPAR活性，特别是PPARα和PPARγ活性，因此可用于有效预防和治疗肥胖症、代谢疾病或心血管疾病的药物组合物或保健食品。