ethyl 3-bromo-3-nitroacrylate | 950854-39-4

• 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: ethyl 3-bromo-3-nitroacrylate
• 英文别名: Ethyl z-3-bromo-3-nitroacrylate；ethyl (Z)-3-bromo-3-nitroprop-2-enoate
• CAS: 950854-39-4
• 化学式: C₅H₆BrNO₄
• 分子量: 224.011
• InChiKey: CAXNPDQVHYMQAI-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 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 3-bromo-3-nitroacrylate 在 三乙胺 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 ethyl (Z)-2-(4-methylphenylamino)-3-nitroacrylate
  参考文献：
  名称：

  3-卤代-3-硝基丙烯酸乙酯：与芳香伯胺的合成和反应

  摘要：

  提出了通过 3-硝基丙烯酸乙酯与 Cl2 或 Br2 反应然后脱卤化氢来合成 Z-3-卤代-3-硝基丙烯酸乙酯的一般程序。首次制得Z-3-氯-3-硝基丙烯酸乙酯。卤代硝基丙烯酸酯与苯胺的反应遵循形成氮杂迈克尔加合物的途径，其脱卤化氢产生新的β-硝基烯胺，即Z-2-芳基氨基-3-硝基丙烯酸乙酯。

  DOI：

  10.1007/s11172-021-3257-5
• 作为产物：
  描述：

  ethyl 2,3-dibromo-3-nitropropionate 在 三乙胺 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以75%的产率得到ethyl 3-bromo-3-nitroacrylate
  参考文献：
  名称：

  3-卤代-3-硝基丙烯酸乙酯：与芳香伯胺的合成和反应

  摘要：

  提出了通过 3-硝基丙烯酸乙酯与 Cl2 或 Br2 反应然后脱卤化氢来合成 Z-3-卤代-3-硝基丙烯酸乙酯的一般程序。首次制得Z-3-氯-3-硝基丙烯酸乙酯。卤代硝基丙烯酸酯与苯胺的反应遵循形成氮杂迈克尔加合物的途径，其脱卤化氢产生新的β-硝基烯胺，即Z-2-芳基氨基-3-硝基丙烯酸乙酯。

  DOI：

  10.1007/s11172-021-3257-5

文献信息

• An Improved, Fully Heterogeneous, Diastereoselective Synthesis of (Z)-α-Bromonitroalkenes
  作者：Roberto Ballini、Alessandro Palmieri、Serena Gabrielli

  DOI：10.1055/s-0032-1317695

  日期：——

  alpha-Bromonitroalkenes are both key starting materials for the preparation of complex structures and possess antimicrobial activity. In this context, we disclose a simple, fully heterogeneous synthetic approach for their preparation in good overall yields.
• Synthesis of 3-Bromo-3-nitroacrylates
  作者：Z. M. Sarkisyan、K. D. Sadikov、A. S. Smirnov、A. A. Kuzhaeva、S. V. Makarenko、N. A. Anisimov、L. I. Deiko、V. M. Berestovitskaya

  DOI：10.1023/b:rujo.0000044559.83690.b4

  日期：2004.6
• Reaction of alkyl-3-nitro-and-3-bromo-3-nitroacrylates with 2-(2-nitroethenyl)furan
  作者：V. M. Berestovitskaya、N. A. Anisimova、O. N. Kataeva、G. A. Berkova、A. Jager

  DOI：10.1134/s1070363208050216

  日期：2008.5

  The diene condensation of beta-nitro and beta-bromo-beta-nitroacrylates with 2-(2-nitroethenyl)furan as 1,3-diene leads to a mixture of regioisomeric tetrahydrobenzofurans transforming under the reaction conditions into benzofurancarboxylates due to the easy dehydrohalogenation, denitration, and dehydration. In the case of a gem-bromonitroacrylate reaction takes two routes: diene synthesis and alkylation of the furan ring, the latter process prevailing. The structure of products formed was established by spectral methods. The investigation of geometry of 2-(1-methoxycarbonyl-2-nitroethenyl)-5-(2-nitroethenyl)furan by XRD analysis showed that its vinyl fragments have the coplanar chelate-like structure with the cisoid orientation of the CO2Me and NO2 groups. The ester group deviates from the plane of the the carbon-carbon multiple bond.
• Reaction of 3-nitro-and 3-bromo-3-nitroacrylates with sodium azide
  作者：N. A. Anisimova、V. M. Berestovitskaya、G. A. Berkova、N. G. Makarova

  DOI：10.1134/s107042800705003x

  日期：2007.5

  Reactions of 3-nitro-and 3-bromo-3-nitroacrylates with sodium azide proceed as 1,3-dipolar cycloaddition and lead to the formation of triazolyl-and nitrotriazolylcarboxylates, and also of azido-and azidonitropropenoates.
• Synthesis and structure of 2-(nitromethylene)-2H-1,4-benzothiazin-3(4H)-one
  作者：V. M. Berestovitskaya、V. A. Tafeenko、S. V. Makarenko、K. D. Sadikov、I. V. Chernyshev

  DOI：10.1134/s1070363206010269

  日期：2006.1

  A new representative of benzothiazines, (2Z)-2-(nitromethylene)-2H-1,4-benzothiazin-3(4H)-one, was synthesized, and its structure was studied. According to H-1 NMR, IR, and UV spectral and X-ray diffraction data, the molecules are planar highly conjugated structures that exist in crystal as centrosymmetric dimers; the latter form layers overlapping with each other and held together by strong pi-pi interaction between the carbonyl groups of neighboring layers.