4-(4-methylphenyl)methylene-2-methyl-5(4H)-oxazolone

• 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-(4-methylphenyl)methylene-2-methyl-5(4H)-oxazolone
• 英文别名: 5(4H)-Oxazolone, 2-methyl-4-[(4-methylphenyl)methylene]-；2-methyl-4-[(4-methylphenyl)methylidene]-1,3-oxazol-5-one
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: DRSAXSPSSHVKSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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-(4-methylphenyl)methylene-2-methyl-5(4H)-oxazolone 在 sodium acetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1-(4-(2-methyl-4-(4-methylbenzylidene)-5-oxo-4,5-dihydro-1H-imidazol-1-yl)phenyl)ethylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  Microwave-assisted synthesis and antimicrobial screening of new imidazole derivatives bearing 4-thiazolidinone nucleus

  摘要：

  A new series of compounds 2-((1-(4-(4-arylidene-2-methyl-5-oxo-4,5-dihydro-1H-imidazol-1-yl)phenyl)ethylidene)hydrazono)thiazolidin-4-ones (4a-o) have been synthesized under conventional and microwave irradiation method. All compounds were characterized by IR, H-1 NMR, C-13 NMR and mass spectra. Newly synthesized compounds were screened for their antibacterial and antifungal activities on Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Staphylococcus pyogenes, Candida albicans, Aspergillus niger and Aspergillus clavatus by bioassays, namely serial broth dilution. The synthesized compounds showed potent antimicrobial activity against tested microorganisms. Compounds 4h, 4j, 4m and 4n were the most potent amongst tested compounds.

  DOI：

  10.1007/s00044-012-0190-z
• 作为产物：
  描述：

  对甲基苯甲醛 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 生成 4-(4-methylphenyl)methylene-2-methyl-5(4H)-oxazolone
  参考文献：
  名称：

  具有2,2'-叔丁基甲基膦基的Atropos联苯双膦配体，用于铑催化烯醇酯的不对称加氢

  摘要：

  这是我们先前有关Atropos联苯双膦配体开发的工作的更新。单晶X射线衍射证实了Atropos出乎意料的结构性能，该结果与我们先前工作中所述的计算结果相符。这种具有联苯骨架和2,2'-叔丁基甲基膦基的P-stereogenic bisphosphine配体已被用于Rh催化的烯醇酯的不对称加氢反应，尚未得到广泛研究，可用于合成几种重要的生物活性化合物。尽管在对映选择性方面仍有进一步改进的余地，但本文报道的结果提供了对这类配体的进一步理解。

  DOI：

  10.1002/adsc.201800774

文献信息

• Silver-Promoted Direct Phosphorylation of Bulky C(sp²)–H Bond to Build Fully Substituted β-Phosphonodehydroamino Acids
  作者：Hao-Qiang Cao、Hao-Nan Liu、Zhe-Yuan Liu、Baokun Qiao、Fa-Guang Zhang、Jun-An Ma

  DOI：10.1021/acs.orglett.0c02229

  日期：2020.8.21

  A general and practical cross-dehydrogenative coupling protocol between readily available trisubstituted α,β-dehydro α-amino carboxylic esters and H-phosphites is described. This C(sp2)–H phosphorylation reaction proceeds with absolute Z-selectivity promoted by silver salt in a radical relay manner. The bulky tetrasubstituted β-phosphonodehydroamino acids were obtained in grams and added new modules

  描述了在容易获得的三取代的α，β-脱氢α-氨基羧酸酯和H-亚磷酸酯之间的一般和实用的交叉脱氢偶联方案。这种C（sp 2）–H磷酸化反应以自由基中继方式通过银盐促进的绝对Z选择性进行。获得了以克为单位的庞大的四取代的β-膦酰基氢氨基酸，并将其添加到用于肽修饰的工具箱中的新模块。
• A concise approach to polysubstituted oxazoles from N-acyl-2-bromo enamides via a copper(<scp>i</scp>)/amino acid-catalyzed intramolecular C–O bond formation
  作者：Bingjie Liu、Yueteng Zhang、Gang Huang、Xinting Zhang、Pengfei Niu、Jie Wu、Wenquan Yu、Junbiao Chang

  DOI：10.1039/c4ob00309h

  日期：——

  intramolecular Ullmann-type C–O coupling reaction has been developed. This protocol affords a facile methodology for the synthesis of a series of novel 2,4,5-substituted oxazoles from readily accessible N-acyl-2-bromo enamides under mild conditions.

  已经开发出一种简单有效的铜（I）/氨基酸催化的分子内乌尔曼型C–O偶联反应。该方案提供了在温和的条件下从容易获得的N-酰基2-溴代酰胺类化合物合成一系列新颖的2,4,5-取代的恶唑的简便方法。
• Synthesis and preliminary biological evaluation of antibacterial and antifungal 5‐arylidene tetramic acid‐cadmium(II) complexes
  作者：Dimitris Matiadis、Valentina Stefanou、Dimitrios Tsironis、Angeliki Panagiotopoulou、Olga Igglessi‐Markopoulou、John Markopoulos

  DOI：10.1002/ardp.202100305

  日期：2021.12

  The synthesis and biological evaluation of 5-arylidene-N-acetyl-tetramic acids cadmium(II) complexes are reported. Eleven novel compounds were prepared, characterized by nuclear magnetic resonance experiments and screened for their antimicrobial activity against five bacterial species (Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and methicillin-resistant

  报道了 5-亚芳基-N-乙酰基四酸镉 (II) 配合物的合成和生物学评价。制备了 11 种新化合物，通过核磁共振实验对其进行了表征，并筛选了它们对 5 种细菌（大肠杆菌、肺炎克雷伯菌、鲍曼不动杆菌、铜绿假单胞菌和耐甲氧西林金黄色葡萄球菌[MRSA]）和两种真菌（念珠菌）的抗菌活性。白色念珠菌和新型隐球菌）。与相应的配体相比，该复合物对 MRSA 显示出相似或增强的活性，此外，对C.neoformans的抗真菌活性有希望. 最活跃的化合物3c和3h对 MRSA（最小抑制活性 [MIC] 值分别为 32 和 4 μg/ml）和新型隐球菌（MIC 值分别为 8 和 16 μg/ml）显示出显着的活性，同时伴随在测试浓度范围内无人体细胞毒性和溶血活性。结果表明，与亲脂性链烷酰基链连接并与镉（II）离子络合后适当官能化的特里马酸可以作为有价值的先导化合物，用于进一步研究新型抗菌和/或抗真菌剂的开发。
• Mechanistically Guided One Pot Synthesis of Phosphine‐Phosphite and Its Implication in Asymmetric Hydrogenation
  作者：Anirban Sen、Rohit Kumar、Swechchha Pandey、K. Vipin Raj、Pawan Kumar、Kumar Vanka、Samir H. Chikkali

  DOI：10.1002/ejoc.202101447

  日期：2022.1.17

  Synthesis of hybrid phosphorus ligands is a multistep, time-consuming exercise. This limitation has been addressed by meticulous understanding of the process of formation of hybrid ligands and a one pot synthesis of a phosphine-phosphite ligand (L1) is reported for the first time. L1 coordinates to Rh and catalyzes asymmetric hydrogenation of 15 substrates with a high TOF of 2289 and enantiomeric excess

  杂化磷配体的合成是一项多步骤、耗时的工作。通过对杂化配体形成过程的细致了解，这一限制得到了解决，并且首次报道了膦-亚磷酸酯配体 (L1) 的一锅合成。L1 与 Rh 配位并催化 15 种底物的不对称氢化，具有 2289 的高 TOF 和 92% 的对映体过量。
• Construction of Chiral-Fused Tricyclic γ-Lactams via a <i>trans</i>-Perhydroindolic Acid-Catalyzed Asymmetric Domino Reaction
  作者：Qianjin An、Jiefeng Shen、Delong Liu、Yangang Liu、Wanbin Zhang

  DOI：10.1021/acs.orglett.7b01160

  日期：2017.6.2

  An asymmetric domino reaction was developed utilizing readily available cyclic α-dehydroamino ketones and aldehydes, which when subjected a 2-iodoxybenzoic acid (IBX)-mediated oxidation gives pyrrolidinone-containing tricyclic derivatives. trans-Perhydroindolic acid proved to be an efficient organocatalyst in this reaction (up to 94% yield, 99% ee, and >20:1 dr). The product could be conveniently converted

  利用容易获得的环状α-脱氢氨基酮和醛开发了不对称的多米诺反应，当进行2-碘氧基苯甲酸（IBX）介导的氧化时，会得到含吡咯烷酮的三环衍生物。反-过氢吲哚酸被证明是该反应中有效的有机催化剂（产率高达94％，ee高达99％，dr> 20：1）。可以通过简单的转化将产物方便地转化为合成有用的中间体。根据X射线晶体学研究已经提出了可能的立体控制过程。