2-Phenyl-4-[1-m-tolyl-meth-(Z)-ylidene]-4H-oxazol-5-one | 72615-35-1

• 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: 2-Phenyl-4-[1-m-tolyl-meth-(Z)-ylidene]-4H-oxazol-5-one
• 英文别名: (4Z)-4-[(3-methylphenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 72615-35-1
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: LEXVKGPAPSCICD-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  2-Phenyl-4-[1-m-tolyl-meth-(Z)-ylidene]-4H-oxazol-5-one 在 Ru(bpy)₃(BF₄)₂ 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  从 4-Arylidene-5(4H)-oxazolones 立体选择性钌光催化合成 1,2-Diaminotruxinic Bis-氨基酸

  摘要：

  ( Z )-2-phenyl-4-aryliden-5(4 H )-oxazolones 1在脱氧 CH 2 Cl 2中在 [Ru(bpy) 3存在下于 25 °C 用蓝光 (465 nm) 照射](BF 4 ) 2 (5% 摩尔比)作为三重态光催化剂促进 4-亚芳基部分的 C=C 键的 [2+2] 光环加成，从而允许完全区域和立体选择性形成环丁烷-双(恶唑酮)s 2作为单一立体异构体。环丁烷2已明确表征为 μ-异构体，并包含两个E-恶唑酮以抗-头对头形式。在微反应器中使用连续流动技术可以在 60 分钟内合成环丁烷2 ，而间歇模式需要 24-48 小时。2中的恶唑酮杂环与碱开环得到相应的 1,2-二氨基松香酸双氨基酯3，其也可选择性地以 μ-异构体的形式获得。钌配合物作为三重态光催化剂，通过能量转移过程产生恶唑酮的反应激发态。这种反应激发态已被表征为三重态双自由基3 ( E / Z )-

  DOI：

  10.1021/acs.joc.1c03092
• 作为产物：
  描述：

  马尿酸 、 3-甲基苯甲醛 在 sodium acetate 、 乙酸酐 作用下， 生成 2-Phenyl-4-[1-m-tolyl-meth-(Z)-ylidene]-4H-oxazol-5-one
  参考文献：
  名称：

  Alkaabi, Sharifa S.; Shawali, Ahmad S., Canadian Journal of Chemistry, 1992, vol. 70, # 10, p. 2515 - 2519

  摘要：

  DOI：

文献信息

• Enantioselective synthesis of optically active cis-β-thio-α-amino acid derivatives through an organocatalytic cascade thio-Michael/ring opening process
  作者：Zhi-Cong Geng、Ning Li、Jian Chen、Xiao-Fei Huang、Bin Wu、Guo-Gui Liu、Xing-Wang Wang

  DOI：10.1039/c2cc30799e

  日期：——

  Non-naturally enantioenriched cis-β-thio-α-amino acid derivatives were synthesized through one pot, cascade thio-Michael/ring opening reaction of aromatic thiols with (Z)-olefinic azlactones in good yields with high levels of diastereoselectivities and enantioselectivities, which was catalyzed by a chiral bifunctional thiourea–tertiary amine catalyst.

  通过芳香硫醇与（Z）-烯烃氮内酯的一锅法、级联硫代-迈克尔/开环反应，合成了非天然对映富集的顺式-β-硫代-α-氨基酸衍生物，收率较高，具有高水平的立体选择性及对映选择性，该反应由手性双功能硫脲-叔胺催化剂催化。
• Synthesis of 1,2-diaminotruxinic δ-cyclobutanes by BF₃-controlled [2 + 2]-photocycloaddition of 5(4<i>H</i>)-oxazolones and stereoselective expansion of δ-cyclobutanes to give highly substituted pyrrolidine-2,5-dicarboxylates
  作者：Sonia Sierra、Rosa López、Enrique Gómez-Bengoa、Larry R. Falvello、Esteban P. Urriolabeitia

  DOI：10.1039/d3ob00284e

  日期：——

  (465 nm) in the presence of the photosensitizer [Ru(bpy)3](BF4)2 (2.5 mol%) and the Lewis acid BF3·OEt2 (2 equiv.) in deoxygenated methanol at room temperature affords the corresponding 1,2-diaminotruxinic cyclobutane bis-amino esters 2a–2u stereoselectively as the δ-isomer. Characterization of cyclobutanes 2 shows that the photocycloaddition takes place by the coupling of two Z-oxazolones in a head-to-head

  在光敏剂 [ Ru ( bpy ) 3 ] (BF 4 ) 2 (2.5 mol% ) 存在下用蓝光 (465 nm) 照射 ( Z )-4-arylidene- 5(4 H ) -oxazolones 1a –1u ) 和路易斯酸 BF 3 ·OEt 2（2 当量）在室温下脱氧甲醇中得到相应的 1,2-二氨基环丁烷双氨基酯2a–2u立体选择性作为 δ 异构体。环丁烷2的表征表明，光环加成是通过两个Z-恶唑酮在头对头 1,2-反方式。BF 3添加剂的O-或/和N-键促进了偶联取向的这种变化。在存在 NaOMe（1/1 摩尔比）的情况下，在甲醇中加热时， δ-环丁烷2会发生扩环，以区域和立体选择性方式生成密集取代的吡咯烷-2,5-二羧酸盐3 。已经使用 DFT 方法阐明了环丁烷到吡咯烷扩环的机理。
• Design, synthesis and evaluation of novel phenyl propionamide derivatives as non-nucleoside hepatitis B virus inhibitors
  作者：Jingying Qiu、Qineng Gong、Jian Gao、Wang Chen、Yinpeng Zhang、Xiaoke Gu、Daoquan Tang

  DOI：10.1016/j.ejmech.2017.12.042

  日期：2018.1

  As an ongoing search for potent non-nucleoside anti-HBV agents with novel structures, we described a series of phenyl propionamide derivatives (3a-b, 4a-e, 7a-g, 8a-h and 9a-b) by pharmacophore fusion strategy in the present work. All the compounds exhibited an anti-HBV activity to some extent. Among them, compounds 8d and 9b displayed most potent anti-HBV activity with IC50 values on HBV DNA replication of 0.46 and 0.14 mu M, respectively. And the selective index values of 8d and 9b were more than 217.39 and 153.14, suggesting that 8d and 9b exhibited favorable safety profiles. Interestingly, 8d and 9b possessed significantly antiviral activities against lamivudine and entecavir resistant HBV mutants with IC50 values of 0.77 and 0.32 mu M. Notably, preliminary anti-HBV action mechanism studies showed that 8d could inhibit intracellular HBV pgRNA and RT activity of the HBV polymerase. Molecular docking studies suggested that compound 8d could fit into the dimer-dimer interface of HBV core protein by hydrophobic interaction. In addition, in silico prediction of physicochemical properties showed that 8d conformed well to the Lipinski's rule of five, suggesting its potential for use as a drug like molecule. Taken together, 8d possessed significantly anti-HBV activity, low toxicity, diverse anti-HBV mechanism and favorable physicochemical properties, and warranted further investigation as a promising non-nucleoside anti-HBV candidate. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Synthesis of isomeric methyl- and dimethyl-substituted 4-benzylidene-2-phenyloxazolin-5-ones and ring-opened derivatives
  作者：Everton S. Nicholas、David J. Phelps

  DOI：10.1021/je60084a033

  日期：1980.1
• NICHOLAS E. S.; PHEIPS D. J., J. CHEM. AND ENG. DATA, 1980, 25, NO 1, 89-90
  作者：NICHOLAS E. S.、 PHEIPS D. J.

  DOI：——

  日期：——