ethyl 2,3-dibromo-3-nitroacrylate | 1224627-77-3

• 分子结构分类: 有机化合物
• 英文名称: ethyl 2,3-dibromo-3-nitroacrylate
• 英文别名: ethyl 2,3-dibromo-3-nitroprop-2-enoate
• CAS: 1224627-77-3
• 化学式: C₅H₅Br₂NO₄
• 分子量: 302.907
• InChiKey: CCPZPLVETDKDNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-dibromo-3-nitroacrylate 、 4-氯苯硫酚 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以40%的产率得到ethyl 3-bromo-2-(4-chlorophenylsulfanyl)-3-nitroacrylate
  参考文献：
  名称：

  Synthesis and structure of new β-functionalized gem-bromonitroethenes — 2-arylsulfanyl- and 2-aryloxy-3-bromo-3-nitroacrylates

  摘要：

  烯丙基2,3-二溴-3-硝基丙烯酸酯与芳硫醇和苯酚反应，生成早期未知的β-官能化双溴硝基乙烯的代表物，即2-芳硫基-和2-芳氧基-3-溴-3-硝基丙烯酸酯；它们的结构通过IR、UV和NMR（1H，13C{1H}，HMQC，HMBC）光谱进行表征。X射线衍射分析显示，甲基3-溴-2-(4-氯苯硫基)-3-硝基丙烯酸酯具有Z构型；其分子中的硫基溴硝基乙烯片段相对共平面，而酯基几乎垂直于C-C双键平面。

  DOI：

  10.1007/s11172-020-3021-2

文献信息

• Synthesis and structure of alkyl-α-arylamino-β-bromo-β-nitroacrylates, new functionalized β-nitroenamines
  作者：V. M. Berestovitskaya、S. V. Makarenko、K. S. Kovalenko、I. A. Litvinov、D. B. Krivolapov、A. D. Shevchenko

  DOI：10.1134/s1070363211020162

  日期：2011.2

  New bromonitroenamine compounds, alkyl-2-arylamino-3-bromo-3-nitroacrylates, were synthesized and characterized using IR, UV, H-1 and C-13 NMR spectroscopy, and X-ray analysis. Their molecules were found to have the E-configuration and to exist as highly conjugated structures. According to the X-ray analysis, in the ethyl-3-bromo-2-(p-bromophenylamino)-3-nitroacrylate molecule the bromonitroenamine moiety is almost planar, the ester group is located completely out of the C=C double bond plane, amino hydrogen and nitro oxygen atoms form an intramolecular hydrogen bond.
• Alkyl-2,3-dibromo-3-nitroacrylates in the reactions with substituted hydrazines
  作者：S. V. Makarenko、K. S. Kovalenko、V. M. Berestovitskaya、M. M. Zobacheva

  DOI：10.1134/s1070363213090193

  日期：2013.9

  The interaction of alkyl 2,3-dibromo-3-nitroacrylates with aroylhydrazines at room temperature or with 2,4-dinitrophenylhydrazine under reflux gives the corresponding 2-aroyl(aryl)hydrazono-3-bromo-3-nitropropanoates. Refluxing of ethyl 2,3-dibromo-3-nitroacrylate with a fourfold excess of benzoylhydrazine results in ethyl-2,3-bis(benzoylhydrazono)propanoate. The structure of compounds obtained has been proved by IR, H-1 NMR, C-13-H-1} NMR, and electron spectroscopy methods.
• Alkyl 2,3-dibromo-3-nitroacrylates in the reaction with o-phenylenediamine
  作者：K. V. Kovalenko、S. V. Makarenko、K. V. Altukhov、V. M. Berestovitskaya

  DOI：10.1134/s1070363210010275

  日期：2010.1
• One-pot synthesis of substituted 1,3-benzothiazole and 1,4-benzothiazinone from dibromonitroacrylates
  作者：S. V. Makarenko、K. S. Kovalenko、Ya. S. Vershinina、V. M. Berestovitskaya

  DOI：10.1134/s1070428014010163

  日期：2014.1

  Alkyl 2,3-dibromo-3-nitroacrylates reacted with 2-aminobenzenethiol at 18-20A degrees C in benzene to give alkyl 1,3-benzothiazole-2-carboxylates, whereas in glacial acetic acid 2-nitromethylidene-2H-1,4-benzothiazin-3(4H)-one was obtained.