4-cyclohexylidene-2-phenyloxazol-5(4H)-one | 52956-46-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-cyclohexylidene-2-phenyloxazol-5(4H)-one
• 英文别名: 2-Phenyl-4-cyclohexyliden-oxazolon-(5)；4-cyclohexylidene-2-phenyl-2-oxazolin-5-one；4-Cyclohexyliden-2-phenyl-5(4H)-oxazolon；5(4H)-Oxazolone, 4-cyclohexylidene-2-phenyl-；4-cyclohexylidene-2-phenyl-1,3-oxazol-5-one
• CAS: 52956-46-4
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: OTXQQAAIQJZVKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-cyclohexylidene-2-phenyloxazol-5(4H)-one 在 palladium on activated charcoal 盐酸 、 ammonium hydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 生成 L-环己基甘氨酸
  参考文献：
  名称：

  Ali,M. et al., Synthetic Communications, 1976, vol. 6, p. 227 - 235

  摘要：

  DOI：
• 作为产物：
  描述：

  马尿酸 在 氯甲酸乙酯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 2.17h， 生成 4-cyclohexylidene-2-phenyloxazol-5(4H)-one
  参考文献：
  名称：

  Condensation of 2-Substituted 5-Oxo-4,5-dihydro-1,3-oxazoles with Imines and Their Corresponding Carbonyl Compounds

  摘要：

  DOI：

  10.1055/s-1980-29228

文献信息

• Microwave-Assisted Erlenmeyer Synthesis of Azlactones Catalyzed by MgO/Al₂O₃Under Solvent-Free Conditions
  作者：Nader Rostamizadeh、Alireza Khajeh-Amiri、Hassan Moghanian

  DOI：10.1080/15533174.2014.989575

  日期：2016.5.3

  MgO/Al2O3 catalyzes the synthesis of azlactone derivatives from condensation reaction of aldehydes (or ketones) with hippuric acid and acetic anhydride as a dehydrating agent under microwave irradiation. The low toxicity, low cost, ease of handling, and high activity of MgO/Al2O3 make this procedure particularly attractive. Also, this catalyst can be easily recovered by decant and can be reused for

  MgO / Al 2 O 3催化醛（或酮）与作为脱水剂的马尿酸和乙酸酐的缩合反应在微波辐射下的合成内酯衍生物。MgO / Al 2 O 3的低毒性，低成本，易于处理和高活性使该程序特别有吸引力。同样，该催化剂可以容易地通过倾析回收，并且可以连续五次重复用于该缩合反应，而不会显着降低其催化活性。
• Microwave-assisted efficient synthesis of azlactones using zeolite NaY as a reusable heterogeneous catalyst
  作者：Mohammad Ali Bodaghifard、Hassan Moghanian、Akbar Mobinikhaledi、Fatemeh Esmaeilzadeh

  DOI：10.1080/15533174.2016.1212242

  日期：2017.6.3

  azlactones in the presence of zeolite NaY has been reported. This heterogeneous catalyst was used for efficient synthesis of azlactone derivatives with Ac2O as a condensing agent under microwave irradiation and solvent-free conditions. The present method offers the advantages of good yields, short reaction time, simple work-up, and catalyst reusability, which makes this method mild and eco-friendly.

  已经报道了在NaY沸石存在下有效制备氮杂内酯的方法。该多相催化剂用于在微波辐射和无溶剂条件下以Ac2O为缩合剂高效合成内酯衍生物。本方法具有收率高，反应时间短，后处理简单，催化剂可重复使用的优点，使该方法温和环保。
• Syntheses of β-lactams from acetic acids and imines induced by phenyl dichlorophosphate reagent
  作者：Ana Arrieta、Fernando P. Cossio、Claudio Palomo

  DOI：10.1016/s0040-4020(01)96484-1

  日期：——

  Among the reagents known to produce β-lactams from imines and acetic acids, only phenyl dichlorophosphate and 1-methyl-2-chloropyridinium iodide are suitable for the synthesis of vinylamino- β-lactams. Reaction of acetic acids with ethanolimine derivatives promoted by phenyl dichlorophosphate affords oxazolidines instead β-lactams. Protection of the hydroxyl group as the trimethylsilyl ether in the

  描述了从丹尼盐和席夫碱制备乙烯基氨基-β-内酰胺的实用方法的开发。在已知可从亚胺和乙酸生产β-内酰胺的试剂中，只有苯基二氯磷酸酯和1-甲基-2-氯吡啶碘代碘适合用于合成乙烯基氨基-β-内酰胺。乙酸与由二氯磷酸苯酯促进的乙醇亚胺衍生物反应生成恶唑烷，而不是β-内酰胺。在起始席夫碱中保护羟基作为三甲基甲硅烷基醚提供了通往相应的β-内酰胺而不是恶唑烷的便利途径。对该方法的范围进行了一些观察。
• 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。
• Dodecatungstophosphoric Acid (H3PW12O40), Samarium and Ruthenium (ІІІ) Chloride Catalyzed Synthesis of Unsaturated 2-Phenyl-5(4H)-oxazolone Derivatives under Solvent-free Conditions
  作者：Ahmad Tikdari、Samieh Fozooni、Hooshang Hamidian

  DOI：10.3390/molecules13123246

  日期：——

  We found that dodecatungstophosphoric acid (H(3)PW(12)O40), samarium and ruthenium(III) chloride act as efficient catalysts for synthesis of unsaturated 2-phenyl-5(4H)oxazolone derivatives under solvent-free conditions. The key features of the reported protocols are short reaction times, high yields of products, ambient conditions and simple workup.

  我们发现十二钨磷酸 (H(3)PW(12)O40)、钐和氯化钌 (III) 可作为无溶剂条件下合成不饱和 2-苯基-5(4H) 恶唑酮衍生物的有效催化剂。报告的协议的主要特点是反应时间短、产品产量高、环境条件和简单的后处理。