methyl 4-bromo-5-phenyl-1,3-oxazole-2-carboxylate | 1126887-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 4-bromo-5-phenyl-1,3-oxazole-2-carboxylate
• 英文别名: Methyl 4-bromo-5-phenyl-1,3-oxazole-2-carboxylate
• CAS: 1126887-91-9
• 化学式: C₁₁H₈BrNO₃
• 分子量: 282.093
• InChiKey: GPXWLTZWQMDROU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 2-benzoyl-2-bromo-2H-azirine-3-carboxylate 以 甲苯 为溶剂， 反应 5.0h， 以97%的产率得到methyl 4-bromo-5-phenyl-1,3-oxazole-2-carboxylate
  参考文献：
  名称：

  4-Halo-1,3-oxazoles: Unambiguous structural assignment of 2-halo-2-benzoyl-2H-azirine-3-carboxylates thermal ring expansion products

  摘要：

  IR spectroscopy in cryogenic argon matrix of methyl 4-chloro-5-phenyl-1,3-oxazole-2-carboxylate and methyl 4-chloro-5-phenylisoxazole-3-carboxylate was applied for the structural assignment of these isomeric heterocycles. It was demonstrated that methyl 2-benzoyl-2-halo-2H-azirine-3-carboxylates undergo thermal ring expansion to give 4-halo-5-phenyl-1,3-oxazole-2-carboxylates and not the isomeric isoxazoles. (c) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2008.08.014

文献信息

• On the photophysical behaviour of 4-halo-5-phenyl-oxazoles and isoxazoles: A correction and observations on the photoinduced isomerisation and degradation of methyl 4-halo-5-phenyl-isoxazole-3-carboxylates
  作者：Sofia M. Fonseca、Hugh D. Burrows、Cláudio M. Nunes、Teresa M.V.D. Pinho e Melo

  DOI：10.1016/j.cplett.2009.04.028

  日期：2009.5

  Photophysical data in cyclohexane solutions, including measurements of energies of lowest excited singlet and triplet states, fluorescence quantum yields, lifetimes, phosphorescence and triplet-singlet difference absorption spectra, reported in a previous Letter as due to methyl 4-halo-5-phenylisoxazole-3-carboxylates [S. M. Fonseca, H.D. Burrows, C.M. Nunes, T.M.V.D. Pinho e Melo, A.M.d'A. Rocha Gonsalves, Chem. Phys. Lett. 414 (2005) 98] are reassigned to the isomeric oxazoles. These are compared with data on the isoxazoles synthesised by an unambiguous route. In addition, results are presented on the photoinduced isomerization of 4-halo-5-phenylisoxazoles to oxazoles in cyclohexane, which is shown to proceed via a nonconcerted pathway, possibly involving thermal reaction of an azirine intermediate. (C) 2009 Elsevier B. V. All rights reserved.
• 4-Halo-1,3-oxazoles: Unambiguous structural assignment of 2-halo-2-benzoyl-2H-azirine-3-carboxylates thermal ring expansion products
  作者：Susy Lopes、Cláudio M. Nunes、Rui Fausto、Teresa M.V.D. Pinho e Melo

  DOI：10.1016/j.molstruc.2008.08.014

  日期：2009.2

  IR spectroscopy in cryogenic argon matrix of methyl 4-chloro-5-phenyl-1,3-oxazole-2-carboxylate and methyl 4-chloro-5-phenylisoxazole-3-carboxylate was applied for the structural assignment of these isomeric heterocycles. It was demonstrated that methyl 2-benzoyl-2-halo-2H-azirine-3-carboxylates undergo thermal ring expansion to give 4-halo-5-phenyl-1,3-oxazole-2-carboxylates and not the isomeric isoxazoles. (c) 2008 Elsevier B.V. All rights reserved.