3,4-dimethoxy-β-bromo-β-nitrostyrene | 55648-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-dimethoxy-β-bromo-β-nitrostyrene
• 英文别名: ω-Brom-3,4-dimethoxy-ω-nitrostyrol；β-bromo-3,4-dimethoxy-β-nitro-styrene；β-Brom-3,4-dimethoxy-β-nitro-styrol；4-(2-Bromo-2-nitroethenyl)-1,2-dimethoxybenzene
• CAS: 55648-19-6
• 化学式: C₁₀H₁₀BrNO₄
• 分子量: 288.098
• InChiKey: WXGKHZRGFQJZTA-UHFFFAOYSA-N

物化性质

• 熔点：
  139 °C
• 沸点：
  368.6±42.0 °C(Predicted)
• 密度：
  1.535±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxy-β-bromo-β-nitrostyrene 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Reichert; Koch, Chemische Berichte, 1935, vol. 68, p. 445,450

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氯仿 、 溴 作用下， 生成 3,4-dimethoxy-β-bromo-β-nitrostyrene
  参考文献：
  名称：

  GB934381

  摘要：

  公开号：

文献信息

• Quinonoid compounds via reactions of lawsone and 2-aminonaphthoquinone with α-bromonitroalkenes and nitroallylic acetates: Structural diversity by C-ring modification and cytotoxic evaluation against cancer cells
  作者：Thekke V. Baiju、Renata G. Almeida、Sudheesh T. Sivanandan、Carlos A. de Simone、Lucas M. Brito、Bruno C. Cavalcanti、Claudia Pessoa、Irishi N.N. Namboothiri、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.ejmech.2018.03.079

  日期：2018.5

  Morita-Baylis-Hillman acetates and α-bromonitroalkenes have been employed in cascade reactions with lawsone and 2-aminonaphthoquinone for the one-pot synthesis of heterocycle fused quinonoid compounds. The reactions reported here utilized the 1,3-binucleophilic potential of hydroxy- and aminonaphthoquinones and the 1,2/1,3-bielectrophilic potential of bromonitroalkenes and Morita-Baylis-Hillman acetates

  Morita-Baylis-Hillman乙酸盐和α-溴硝基烯烃已用于与Lawone和2-氨基萘醌的级联反应，用于一锅合成杂环稠合的醌类化合物。此处报道的反应利用羟基和氨基萘醌的1,3-双亲核势以及溴硝基烯烃和Morita-Baylis-Hillman乙酸酯的1,2 / 1,3-双亲电势来合成吡咯和呋喃稠合的萘醌。对合成的化合物针对HCT-116（人类结肠癌细胞），PC3（人类前列腺癌细胞），HL-60（人类早幼粒细胞白血病细胞），SF295（人类胶质母细胞瘤细胞）和NCI-H460（人类肺癌细胞）进行了评估。并显示出抗肿瘤活性，IC50值低至<2μM。还针对OVCAR-8（卵巢）评估了选定的化合物，MX-1（乳腺癌）和JURKAT（白血病）细胞系。还使用非肿瘤细胞测定了评价的醌类的细胞毒性潜力，例如外周血单核（PBMC）和L929细胞。
• Synthesis, Antimicrobial Study, and Molecular Docking Simulation of 3,4-Dimethoxy-β-Nitrostyrene Derivatives as Candidate PTP1B Inhibitor
  作者：Salman Alfarisi、Mardi Santoso、Alfinda Novi Kristanti、Imam Siswanto、Ni Nyoman Tri Puspaningsih

  DOI：10.3390/scipharm88030037

  日期：——

  A derivative series of 3,4-dimethoxy-β-nitrostyrene was synthesized through nitroaldol reaction, including a new compound of 3,4-ethylenedioxy-β-bromo-β-nitrostyrene. The antimicrobial activity effect of 3,4-alkyloxy modification of β-nitrostyrene was investigated. A molecular docking study was also performed to obtain information about their interactions with protein tyrosine phosphatase 1B (PTP1B). The active residues of cysteine-215 and arginine-221 of PTP1B play a key role in signaling pathways that regulate various microorganism cell functions. It also acts as a negative regulator in signaling pathways of insulin that are involved in type 2 diabetes and other metabolic diseases. These derivatives exhibited potential antifungal activity. The studied compounds were also had potential as fragments to be PTP1B inhibitors by interacting with serine-216 and arginine-221 residues, according to their molecular docking. 3,4-Ethylenedioxy-β-methyl-β-nitrostyrene was the most successful potential candidate as a PTP1B inhibitor. However, further research is needed to investigate their potential for medicinal use.

  一系列3,4-二甲氧基-β-硝基苯乙烯的衍生物通过硝基醛醇反应合成，包括一种新化合物3,4-乙二氧基-β-溴-β-硝基苯乙烯。研究了β-硝基苯乙烯的3,4-烷氧基修饰对抗菌活性的影响。还进行了分子对接研究，以获取它们与蛋白酪氨酸磷酸酶1B（PTP1B）的相互作用信息。PTP1B的半胱氨酸-215和精氨酸-221的活性残基在调节各种微生物细胞功能的信号通路中起关键作用。它还在参与第2型糖尿病和其他代谢性疾病的胰岛素信号通路中充当负调节因子。这些衍生物表现出潜在的抗真菌活性。根据它们的分子对接，研究化合物也具有潜力作为与丝氨酸-216和精氨酸-221残基相互作用的PTP1B抑制剂片段。3,4-乙二氧基-β-甲基-β-硝基苯乙烯是最成功的潜在PTP1B抑制剂候选化合物。然而，需要进一步研究它们在药用方面的潜力。
• Imidazoles from nitroallylic acetates and α-bromonitroalkenes with amidines: synthesis and trypanocidal activity studies
  作者：Elumalai Gopi、Tarun Kumar、Rubem F. S. Menna-Barreto、Wagner O. Valença、Eufrânio N. da Silva Júnior、Irishi N. N. Namboothiri

  DOI：10.1039/c5ob01444a

  日期：——

  Cascade reactions of amidines with nitroallylic acetates and α-bromonitroalkenes provide potentially bioactive imidazoles in good to excellent yields in most cases. While 2,4-disubstituted imidazol-5-yl acetates are formed in the first case, 2,4-disubstituted imidazoles, bearing no substituent at position 5, are the products in the second case. These two series of imidazoles, viz. 2,4,5-trisubstituted

  在大多数情况下，am与乙酸烯丙酯和α-溴硝基烯烃的级联反应可提供潜在的具有生物活性的咪唑，其收率良好至极佳。在第一种情况下形成2,4-二取代的咪唑-5-基乙酸盐，而在第二种情况下形成2,4-二取代的咪唑，它们在5位不带取代基。这两个咪唑系列，即。筛选了2,4,5-三取代和2,4-二取代的抗原生动物寄生虫克氏锥虫的活性，锥虫是南美锥虫病的病因。多达三种化合物的活性与标准苯并咪唑一样，而另外两种化合物的活性则高2–3倍，这突出了取代的咪唑的潜力，它很容易从硝基烯烃中获得，并可能是抗寄生虫药。
• Synthesis of Densely Substituted Sulfonylfurans and Dihydrofurans via Cascade Reactions of α-Functionalized Nitroalkenes with β-Ketosulfones
  作者：Vaijinath Mane、Sudheesh T. Sivanandan、Rafael G. Santana、Adilson Beatriz、Eufrânio N. da Silva Júnior、Irishi N. N. Namboothiri

  DOI：10.1021/acs.joc.0c00606

  日期：2020.7.17

  substrate scope. Application of these products has been demonstrated by the synthesis of pyrroles and pyrazoles in good yields. The reaction of β-ketosulfones with nitroallylic acetates yields tetrasubstituted sulfonyl furans through a cascade SN2′-intramolecular Michael reaction, followed by aromatization. The gram-scale synthesis of a representative example of sulfonylfurans was carried out to demonstrate

  β-酮砜与不同的α-官能化的硝基烯烃反应可得到取代的磺酰基呋喃和二氢呋喃。此外，β-酮砜通过级联的迈克尔加成环化方案与α-溴硝基烯烃和α-肼基硝基烯烃反应，分别得到带有关键磺酰基的硝基二氢呋喃和肼基二氢呋喃，具有优异的收率，具有广泛的底物范围。这些产品的应用已通过高产率合成吡咯和吡唑得到了证明。β-酮砜与硝基烯丙基乙酸酯的反应通过级联S N生成四取代的磺酰呋喃2'-分子内迈克尔反应，然后进行芳构化。进行了克规模的磺酰呋喃代表性实例的合成，以证明该方法的合成效率。
• CONDENSATION OF VANILLIN SUBSTITUTION PRODUCTS WITH NITROMETHANE
  作者：L. CHAS. RAIFORD、DONALD E. FOX

  DOI：10.1021/jo01184a005

  日期：1944.3