methyl 3-bromo-3-nitroacrylate

• 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: methyl 3-bromo-3-nitroacrylate
• 英文别名: methyl (Z)-3-bromo-3-nitroprop-2-enoate
• 化学式: C₄H₄BrNO₄
• 分子量: 209.984
• InChiKey: NCLVOKYBUSZEAO-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  苯茚二酮 、 methyl 3-bromo-3-nitroacrylate 在 三乙胺 作用下， 以 苯 为溶剂， 以22%的产率得到2-(2-bromo-1-methoxycarbonyl-2-nitroethyl)-2-phenyl-1,3-indanedione
  参考文献：
  名称：

  3-Nitro-and 3-bromo-3-nitroacrylates in reactions with 2-phenyl-1,3-indanedione

  摘要：

  DOI：

  10.1134/s1070428006080264
• 作为产物：
  描述：

  methyl 2,3-dibromo-3-nitropropionate 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 methyl 3-bromo-3-nitroacrylate
  参考文献：
  名称：

  Synthesis of 3-Bromo-3-nitroacrylates

  摘要：

  DOI：

  10.1023/b:rujo.0000044559.83690.b4

文献信息

• 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.
• 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.
• α-Indolyl-β-nitroacrylates. Synthesis and structure
  作者：V. M. Berestovitskaya、S. V. Makarenko、A. S. Smirnov、A. T. Gubaidullin、I. A. Litvinov、A. I. Pekki、Z. M. Sarkisyan

  DOI：10.1134/s1070363208050228

  日期：2008.5

  A one-pot procedure has been developed for the synthesis of alpha-indolyl-beta-nitroacrylates by reaction of beta-bromo-beta-nitroacrilates with indole and substituted indoles. All indolylnitroacrilates thus obtained have Z configuration of the double bond. According to the X-ray diffraction data, ethyl 2-(1-methyl-1H-indol-3-yl)-3-nitroacrylate is characterized by s-trans conformation of the double C=C bond and indole ring; its crystal packing involves intermolecular hydrogen bonds C-H center dot center dot center dot O and C-H center dot center dot center dot pi with formation of centrosymmetric dimers which give rise to bilayer supramolecular structures.
• 3-nitro- and 3-bromo-3-nitroacrylates in reactions with phenyl azide
  作者：V. M. Berestovitskaya、N. A. Anisimova、O. N. Kataeva、N. G. Makarova、G. A. Berkova

  DOI：10.1134/s1070363207090113

  日期：2007.9

  1,3-Dipolar cycloaddition of alkyl 3-nitro-and 3-bromo-3-nitroacrylates to phenyl azide gives regioisomeric alkyl 5(4)-nitro-1-phenyl-4,5-dihydro-1H-1,2,3-triazole-4(5)-carboxylates, the corresponding triazoles both with and without nitro group, and alkyl 3-nitro-1-phenylaziridine-2-carboxylates. Nitrotriazolecarboxylates were found to lose the ester moiety during chromatographic separation of the products on aluminum oxide. The structure of the products was determined on the basis of IR, H-1 NMR, and X-ray diffraction data.
• Synthesis of 2-morpholino(piperidino)-3-nitroacrylates
  作者：K. D. Sadikov、A. S. Smirnov、S. V. Makarenko、V. M. Berestovitskaya

  DOI：10.1007/s11178-005-0061-x

  日期：2004.10