5-(3-nitrophenyl)-2-phenyloxazole | 145930-40-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-nitrophenyl)-2-phenyloxazole
• 英文别名: 5-(3-Nitrophenyl)-2-phenyl-1,3-oxazole
• CAS: 145930-40-1
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: FBZIRYBMVDVULM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[2-(3-Nitro-phenyl)-2-oxo-ethyl]-benzamide 在 硫酸 作用下， 生成 5-(3-nitrophenyl)-2-phenyloxazole
  参考文献：
  名称：

  Combinatorial discovery of novel fluorescent dyes based on Dapoxyl™

  摘要：

  We have developed a combinatorial method for the fast and effective synthesis of a library based on a known fluorescent dye, Dapoxyl(TM) using parallel solution-phase chemistry. By screening the 140 new compounds using fluorescence-based assays, we identified three new fluorescent dyes with novel properties. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00999-1

文献信息

• Formation of Acyl-Substituted Nitrile Ylides by Rh₂(OAc)₄-Catalyzed Decomposition of<i>α</i>-Diazocarbonyl Compounds in Nitriles
  作者：Kazuaki Fukushima、Toshikazu Ibata

  DOI：10.1246/bcsj.68.3469

  日期：1995.12

  The Rh2(OAc)4-catalyzed reactions of α-diazocarbonyl compounds in nitrile in the presence of dimethyl acetylenedicarboxylate (DMAD) gave oxazole and pyrrole derivatives. The formation of the oxazole derivatives is explained in terms of the 1,5-cyclization of an acyl-substituted nitrile ylide intermediate, and the formation of the pyrrole derivatives is explained by the 1,3-dipolar cycloaddition of

  在乙炔二羧酸二甲酯 (DMAD) 存在下，α-重氮羰基化合物在腈中的 Rh2(OAc)4 催化反应得到恶唑和吡咯衍生物。恶唑衍生物的形成通过酰基取代的腈叶立德中间体的 1,5-环化来解释，吡咯衍生物的形成通过相同中间体与 DMAD 的 1,3-偶极环加成来解释。酰基取代的腈叶立德与丙炔酸甲酯的环加成反应的区域化学表明，丙炔基型共振结构的贡献在酰基取代的腈叶立德反应中起重要作用。
• Direct arylations on water: synthesis of 2,5-disubstituted oxazoles balsoxin and texaline
  作者：Stephan A. Ohnmacht、Patrizia Mamone、Andrew J. Culshaw、Michael F. Greaney

  DOI：10.1039/b719466h

  日期：——

  An efficient two-step palladium catalysed synthesis of 2,5-disubstituted oxazoles is reported.

  报告了一种高效的二步钯催化合成2,5-二取代恶唑的方法。
• Formation and Reaction of Acyl Substituted Nitrile Ylide through the Rh₂(OAc)₄-Catalyzed Reaction of α-Diazocarbonyl Compounds with Benzonitrile
  作者：Toshikazu Ibata、Kazuaki Fukushima

  DOI：10.1246/cl.1992.2197

  日期：1992.11

  The rhodium(II) acetate-catalyzed reaction of α-diazocarbonyl compounds with benzonitrile and dimethyl acetylenedicarboxylate gave oxazoles and pyrrole-3,4-dicarboxylates through the 1,5-cyclizatio...

  α-重氮羰基化合物与苯甲腈和乙炔二甲酸二甲酯的乙酸铑（II）催化反应通过 1,5-环化反应得到恶唑和吡咯-3,4-二羧酸酯。
• Metal-Free sp3 C–H Functionalization: PABS/I2-Promoted Synthesis of Polysubstituted Oxazole Derivatives from Arylethanones and 2-Amino-2-alkyl/arylacetic Acid
  作者：Guosheng Huang、Ting Hu、Hao Yan、Xingxing Liu、Chaoyang Wu、Yuxing Fan、Jing Huang

  DOI：10.1055/s-0035-1560660

  日期：——

  nonmetal-catalyzed process for the synthesis of polysubstituted oxazoles from inexpensive and readily available α-amino acids and methyl ketones is established. This reaction is proposed to achieve oxidative cleavage of C(sp 3 )–H bonds, followed by decarboxylation and annulation. The mild reaction conditions employed in both cases enable the tolerance of a wide range of functional groups as well as high reaction

  建立了一种由廉价且容易获得的 α-氨基酸和甲基酮合成多取代恶唑的非金属催化方法。该反应旨在实现 C(sp 3 )-H 键的氧化裂解，然后进行脱羧和环化。在这两种情况下采用的温和反应条件能够耐受广泛的官能团以及高反应效率。
• N-Bromosuccinimide as a Brominating Agent for the Transformation of N-H (or N-Benzyl) Ketoaziridines into Oxazoles
  作者：Heshmat Samimi、Farkhondeh Dadvar

  DOI：10.1055/s-0034-1380518

  日期：——

  A novel procedure for the direct synthesis of 2,5-diaryloxazoles starting from N-H ketoaziridines is described. The method proceeds via the in situ formation of N-bromoketoaziridines in the presence of N-bromosuccinimide followed by the generation of intermediate azomethine ylides. A plausible mechanism for this transformation is proposed.