2-溴-5-[(E)-2-溴-2-硝基乙烯基]呋喃 | 35950-55-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 2-溴-5-[(E)-2-溴-2-硝基乙烯基]呋喃
• 英文名称: 1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene
• 英文别名: 2-bromo-5-(2-bromo-2-nitroethenyl)furan；2-bromo-5-(2-bromo-2-nitrovinyl)furan；furvina；2-bromo-5-(2-bromo-2-nitro-vinyl)-furan；2-bromo-5-(2-bromo-2-nitrovinyl)-furan；β-<5-Brom-furyl-2>-bromnitroethylen
• CAS: 35950-55-1
• 化学式: C₆H₃Br₂NO₃
• 分子量: 296.903
• InChiKey: MJPPGVVIDGQOQT-UHFFFAOYSA-N

物化性质

• 沸点：
  305.2±42.0 °C(Predicted)
• 密度：
  2.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  2-溴-5-[(E)-2-溴-2-硝基乙烯基]呋喃 在 ammonium acetate 、 水 作用下， 以 aq. buffer 为溶剂， 反应 1.5h， 生成 1-(5-bromofur-2-yl)-2-nitroethylene
  参考文献：
  名称：

  Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity

  摘要：

  A di-bromo substituted nitrovinylfuran with reported broad-spectrum antibacterial activity was found to be a potent inhibitor of MurA, a key enzyme in peptidoglycan biosynthesis. Further characterization of the compound was carried out to assess its reactivity towards thiol nucleophiles, its stability and degradation under aqueous conditions, inhibitory potential at other enzymes, and antibacterial and cytotoxic activity. Our results indicate that the nitrovinylfuran derivative is reactive towards cysteine residues in proteins, as demonstrated by the irreversible inhibition of MurA and bacterial methionine aminopeptidase. Experiments with proteins and model thiols indicate that the compound forms covalent adducts with SH groups and induces intermolecular disulfide bonds, with the intermediate formation of a monobromide derivative. The parent molecule as well as most of its breakdown products are potent antibiotics with MIC values below 4 mu g/mL and are active against multiresistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). Further development of the bromonitrovinyl scaffold towards antibiotics with clinical relevance, however, requires optimization of the antibiotic-cytotoxic selectivity profile. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.018
• 作为产物：
  描述：

  5-溴-2-呋喃甲醛 、 溴代硝基甲烷 在 ammonium acetate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以35%的产率得到2-溴-5-[(E)-2-溴-2-硝基乙烯基]呋喃
  参考文献：
  名称：

  Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity

  摘要：

  A di-bromo substituted nitrovinylfuran with reported broad-spectrum antibacterial activity was found to be a potent inhibitor of MurA, a key enzyme in peptidoglycan biosynthesis. Further characterization of the compound was carried out to assess its reactivity towards thiol nucleophiles, its stability and degradation under aqueous conditions, inhibitory potential at other enzymes, and antibacterial and cytotoxic activity. Our results indicate that the nitrovinylfuran derivative is reactive towards cysteine residues in proteins, as demonstrated by the irreversible inhibition of MurA and bacterial methionine aminopeptidase. Experiments with proteins and model thiols indicate that the compound forms covalent adducts with SH groups and induces intermolecular disulfide bonds, with the intermediate formation of a monobromide derivative. The parent molecule as well as most of its breakdown products are potent antibiotics with MIC values below 4 mu g/mL and are active against multiresistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). Further development of the bromonitrovinyl scaffold towards antibiotics with clinical relevance, however, requires optimization of the antibiotic-cytotoxic selectivity profile. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.018

文献信息

• Synthesis of non-racemic dihydrofurans via Ni(II)-catalyzed asymmetric Michael addition
  作者：Dmitry S. Nikerov、Maria A. Ashatkina、Vadim A. Shiryaev、Ilya M. Tkachenko、Victor B. Rybakov、Alexander N. Reznikov、Yuri N. Klimochkin

  DOI：10.1016/j.tet.2021.132029

  日期：2021.3

  A highly efficient strategy for the enantio- and diastereoselective synthesis of 4,5-dihydrofuran derivatives was developed. Addition of carbonyl compounds which contain bulky adamantyl substituent and β-keto or phosphonate group to conjugated α-bromonitroolefins in the presence of a chiral Ni(II) complex gave corresponding non-racemic products of Michael reaction. These adducts were used for intramolecular

  为4,5-二氢呋喃衍生物的对映体和非对映体选择性合成开发了高效策略。在手性Ni（II）配合物的存在下，将含有大量金刚烷基取代基和β-酮基或膦酸酯基的羰基化合物加到共轭的α-溴硝基烯烃上，得到相应的非外消旋迈克尔反应产物。这些加合物用于分子内环化，产生具有两个立体中心的反式-4,5-二氢呋喃。所得的反式以良好的收率与中度至高度的对映选择性（84-99％得到-4,5-二氢呋喃EE）和优良的非对映选择性（博士> 99％）。
• Reaction of 2-(2-bromo-2-nitroethenyl)furan derivatives with dimedone and cyclohexane-1,3-dione
  作者：V. M. Berestovitskaya、S. V. Makarenko、K. A. Lyssenko、S. S. Eliseenko、R. I. Baichurin

  DOI：10.1134/s1070428015090134

  日期：2015.9

  2-Bromo-5-(2-bromo-2-nitroethenyl)furan reacted with cyclohexane-1,3-dione and dimedone on heating in boiling benzene in the presence of triethylamine to give 3-(5-bromofuran-2-yl)-2-nitro-3,5,6,7- tetrahydro-1-benzofuran-4(2H)-ones. Analogous reactions of 5-nitro-2-(2-bromo-2-nitroethenyl)furan led to the formation of 3-(5-nitrofuran-2-yl)-6,7-dihydro-1-benzofuran-4(5H)-ones. The isolated products were character-.
• Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity
  作者：Therese Scholz、Carina L. Heyl、Dan Bernardi、Stefan Zimmermann、Lars Kattner、Christian D. Klein

  DOI：10.1016/j.bmc.2012.11.018

  日期：2013.2

  A di-bromo substituted nitrovinylfuran with reported broad-spectrum antibacterial activity was found to be a potent inhibitor of MurA, a key enzyme in peptidoglycan biosynthesis. Further characterization of the compound was carried out to assess its reactivity towards thiol nucleophiles, its stability and degradation under aqueous conditions, inhibitory potential at other enzymes, and antibacterial and cytotoxic activity. Our results indicate that the nitrovinylfuran derivative is reactive towards cysteine residues in proteins, as demonstrated by the irreversible inhibition of MurA and bacterial methionine aminopeptidase. Experiments with proteins and model thiols indicate that the compound forms covalent adducts with SH groups and induces intermolecular disulfide bonds, with the intermediate formation of a monobromide derivative. The parent molecule as well as most of its breakdown products are potent antibiotics with MIC values below 4 mu g/mL and are active against multiresistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). Further development of the bromonitrovinyl scaffold towards antibiotics with clinical relevance, however, requires optimization of the antibiotic-cytotoxic selectivity profile. (C) 2012 Elsevier Ltd. All rights reserved.