methyl 2-benzoyl-2-bromo-2H-azirine-3-carboxylate | 367967-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-benzoyl-2-bromo-2H-azirine-3-carboxylate
• 英文别名: 2-benzoyl-2-bromo-2H-azirine-3-carboxylate；Methyl 3-benzoyl-3-bromoazirine-2-carboxylate
• CAS: 367967-59-7
• 化学式: C₁₁H₈BrNO₃
• 分子量: 282.093
• InChiKey: XMVHFWVPVKSSHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  methyl 2-azido-3-bromo-3-benzoylpropenoate 生成 methyl 2-benzoyl-2-bromo-2H-azirine-3-carboxylate
  参考文献：
  名称：

  Synthesis and reactivity of 2-halo-2H-azirines towards nucleophiles

  摘要：

  DOI：

  10.1016/s0040-4039(00)01239-9

文献信息

• Reactivity of 2-Halo-2H-azirines. Part II. Thermal Ring Expansion Reactions: Synthesis of 4-Haloisoxazoles
  作者：Teresa M. V. D. Pinho e Melo、Cláudia S. J. Lopes、António M. d’A. Rocha Gonsalves、Richard C. Storr

  DOI：10.1055/s-2002-23542

  日期：——

  The thermolysis of haloazidoalkenes and 2-halo-2H-azirines is described. 2-Benzoyl-2-halo-2H-azirine-3-carboxylates (2a and 2b) underwent ring expansion leading to the synthesis of new 4-haloisoxazoles in high yield. The same isoxazoles were also obtained in high yield directly from haloazidoalkenes (la and 1b). The thermolysis of the β-azido-α,β-unsaturated ketone 1e led to complete conversion to

  描述了卤代叠氮化物和 2-卤代-2H-氮杂环丙烷的热解。2-Benzoyl-2-halo-2H-azirine-3-carboxylates（2a 和 2b）经历了扩环，导致以高产率合成新的 4-haloisoxazoles。同样的异恶唑也可以直接从卤代叠氮烯烃中以高产率获得（la 和 1b）。β-叠氮基-α,β-不饱和酮1e的热解导致完全转化形成相应的异恶唑4e。他还可以从 2-溴-3-苯基-2H-氮杂环丙烷-2-羧酸盐 (1c) 以中等收率获得异恶唑衍生物 4c。从叠氮基烯烃Id的热解中，唯一可以分离的产物是吡嗪-2,3,5,6-四羧酸盐(5)。
• Reactivity of 2-Halo-2<i>H</i>-azirines. 1. Reactions with Nucleophiles
  作者：Teresa M. V. D. Pinho e Melo、Cláudia S. J. Lopes、António M. d'A. Rocha Gonsalves,、Ana M. Beja、José A. Paixão、Manuela R. Silva、Luiz Alte da Veiga

  DOI：10.1021/jo010504v

  日期：2002.1.1

  Nucleophilic substitution reactions of 2-halo-2H-azirines 1a, 1b, 1d, and 1e with potassium phthalimide and aniline allowed the preparation of new substituted 2H-azirines 2-5. The reactions of 2-bromo-2H-azirine la with methylamine led to the synthesis of alpha-diimines 7 and 8. 2-Halo-2H-azirines were also established as building blocks for the synthesis of a range of heterocyclic compounds, namely, quinoxalines 10a-10d, 3-oxazoline 14, and 2H-[1,4]oxazines 18 and 20. X-ray crystal structures of a-diimine 7, 3-oxazoline 14, and 2H-[1,4]oxazine 18 are reported.
• Synthesis and reactivity of 2-halo-2H-azirines towards nucleophiles
  作者：Teresa M.V.D. Pinho e Melo、Cláudia S.J. Lopes、António M.d'A.Rocha Gonsalves

  DOI：10.1016/s0040-4039(00)01239-9

  日期：2000.9
• 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.
• Synthesis of 2-halo-2H-azirines
  作者：Teresa M.V.D Pinho e Melo、Cláudia S.J Lopes、Ana L Cardoso、António M.d'A Rocha Gonsalves

  DOI：10.1016/s0040-4020(01)00598-1

  日期：2001.7