1-(5-bromofur-2-yl)-2-bromo-2-nitroethene | 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
• 英文名称: 1-(5-bromofur-2-yl)-2-bromo-2-nitroethene
• 英文别名: (Z)-2-(2-bromo-2-nitroethenyl)-5-bromofuran；(Z)-2-bromo-5-(2-bromo-2-nitrovinyl)furan；5-bromo-2-(2-bromo-2-nitroethenyl)furan；(Z)-1-bromo-2-(5-bromofuran-2-yl)-1-nitroethene；2-bromo-5-(2-bromo-2-nitrovinyl)-furan；Furvina；2-bromo-5-[(Z)-2-bromo-2-nitroethenyl]furan
• CAS: 35950-55-1
• 化学式: C₆H₃Br₂NO₃
• 分子量: 296.903
• InChiKey: MJPPGVVIDGQOQT-HWKANZROSA-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：

  1-(5-bromofur-2-yl)-2-bromo-2-nitroethene 在 四(三苯基膦)钯 potassium phosphate 作用下， 以 水 、 甲苯 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Synthesis of 2-(2-Arylethenyl)-5-arylfurans by Regioselective Palladium(0)-Catalyzed Coupling Reactions of 2-(2-Bromo-2-nitroethenyl)-5-bromofuran

  摘要：

  2-(2-溴-2-硝基乙烯基)-5-溴呋喃的铃木反应，易于从糠醛获得，导致对呋喃部分的区域选择性攻击。烯基部分可以在第二次铃木反应中进行官能团化。

  DOI：

  10.1055/s-2006-950271
• 作为产物：
  描述：

  β-<5-Brom-furyl-2>-α,β-dibrom-nitro-ethylen 在 potassium acetate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以68%的产率得到1-(5-bromofur-2-yl)-2-bromo-2-nitroethene
  参考文献：
  名称：

  Furan-containing gem-bromonitroethenes: Synthesis and reaction with morpholine

  摘要：

  The first time the representative of furan-containing gem-bromonitroethenes 5-nitro-2-(2-bromo-2-nitro-ethenyl)furan was synthesized by bromination of 5-nitro-2-(2-nitroethenyl)furan followed by dehydrohalogenation of the dibromide. Morpholine adducts of the synthesized beta-substituted gem-bromonitroethene and its analog with a 5-bromo-2-furyl substituent were obtained. The structures of the gem-bromonitroethenes and aza adducts were characterized by spectral methods (IR, UV, H-1, and C-13-{H-1} NMR, including H-1-C-13 HMQC and HMBC).

  DOI：

  10.1134/s1070363215060110

文献信息

• Organocatalytic enantioselective synthesis of dihydronaphthofurans and dihydrobenzofurans: reaction development and insights into stereoselectivity
  作者：Zeynep Dilşad Susam、Bilge Deniz Özcan、Enis Kurtkaya、Erol Yildirim、Cihangir Tanyeli

  DOI：10.1039/d2ob01571d

  日期：——

  Squaramide/cinchona alkaloid-derived bifunctional organocatalysts are in high demand in asymmetric transformations. Bifunctional quinine-derived sterically encumbered squaramide (H-bond donor) organocatalysts were used to catalyze the asymmetric Friedel–Crafts/SN2 type domino reaction of (Z)-α-bromonitroalkenes and α/β-naphthols and phenol derivatives to generate enantiomerically enriched dihydronaphthofuran

  Squaramide/金鸡纳生物碱衍生的双功能有机催化剂在不对称转化中有很高的需求。双功能奎宁衍生的空间阻碍角酰胺（H 键供体）有机催化剂用于催化不对称 Friedel–Crafts/S N 2 型多米诺反应 ( Z)-α-溴硝基烯烃和 α/β-萘酚和苯酚衍生物，分别生成对映体富集的二氢萘并呋喃 (DHN) 和二氢苯并呋喃 (DHB) 衍生物。与文献中已知的方法相比，在温和条件下以相对较低的催化剂负载量 (5 mol%) 获得了高达 >99% ee 的目标加合物。此外，还进行了密度泛函理论 (DFT) 计算以确定可能的结果，解释了立体选择性的起源。据发现，Friedel-Crafts 步骤中反式构象的 π 堆叠相互作用比顺式构象稳定 0.79 kcal mol -1。
• METHOD FOR OBTAINING 2-BROMO-5-(2-BROMO-2-NITROVINYL)-FURAN
  申请人：Centro De Bioactivos Quimicos (CBQ)

  公开号：EP1249449A1

  公开（公告）日：2002-10-16

  The present invention refers to a new procedure for obtaining and purifying 2-bromo-5-(2-bromo-2-nitrovinyl)-furan in one reaction step starting with 2-nitrovinylfuran, and maintains high indexes of purity and an appropriate yield. The process involves the direct bromination of 2-nitrovinylfuran using charcoal from the beginning of the reaction, followed by the neutralization and dehydrobromination using pyridine, and finally crystallizing and purifying the product obtained with ethanol and charcoal. With the new procedure it is possible to reduce the time of obtaining the final product, the reaction becomes endothermic instead of exothermic, which facilitates the work of the operators and allows for the scaling up of the reaction to superior levels. The process significantly decreases the amount of chemicals in the reaction, some of them with toxic properties. Also the environmental negative impact from the process is diminished as the emission of the bromine vapors and other substances to the environment are eliminated and the residual liquids are cut in half.

  本发明是指一种以 2-硝基乙烯基呋喃为原料，通过一个反应步骤获得和纯化 2-溴-5-(2-溴-2-硝基乙烯基)-呋喃，并保持高纯度指标和适当收率的新工艺。 该工艺包括在反应开始时使用木炭直接溴化 2-硝基乙烯基呋喃，然后使用吡啶中和并脱氢溴化，最后使用乙醇和木炭结晶并纯化得到的产物。 采用新工艺可以缩短获得最终产品的时间，反应由放热变为内热，从而方便了操作人员的工作，并使反应规模达到更高水平。 该工艺大大减少了反应中化学物质的用量，其中一些化学物质具有毒性。此外，由于消除了向环境排放溴蒸汽和其他物质，残留液体也减少了一半，该工艺对环境的负面影响也随之降低。
• Cochleate with only one mamp
  申请人：Instituto Finlay, Centro de Investigacion-Produccion de vacunas y sueros

  公开号：EP2689775A1

  公开（公告）日：2014-01-29

  The present invention relates to the field of immunology, specifically the branch of adjuvants and vaccines. The technical objective is to obtain adjuvants based on cochlear structures that are neither proteolipidic nor lipidic and that contain microbe-associated molecular patterns (MAMPs) and have the optional addition of antibiotics/chemotherapeutic agents with the aim of using them as vaccine adjuvants for the treatment and prevention of veterinary and human diseases. Additionally, these would be used as immunopotentiators in veterinary and human formulations. It is also a technical objective of this patent to utilize the said new cochlear structures with particular antigens added or liberated in vivo for the combined effect of immunopotentiation and antibiotics/chemotherapeutic agents in infectious diseases to obtain therapeutic vaccines for veterinary and human use in the pharmaceutical industry. The invention also relates to the method for obtaining sterile cochlear structures.

  本发明涉及免疫学领域，特别是佐剂和疫苗分支。其技术目标是获得基于耳蜗结构的佐剂，这种佐剂既不是蛋白脂质的，也不是脂质的，含有微生物相关分子模式（MAMPs），并可选择添加抗生素/化疗药物，目的是将其用作治疗和预防兽医和人类疾病的疫苗佐剂。此外，它们还可用作兽医和人类配方中的免疫促进剂。本专利的另一个技术目标是利用上述新的耳蜗结构，在体内添加或释放特定抗原，在传染病中发挥免疫增强剂和抗生素/化疗药物的联合作用，以获得用于制药业的兽用和人用治疗疫苗。本发明还涉及获得无菌耳蜗结构的方法。
• Method for obtaining 2-bromo-5-(2-bromo-2-nitrovinyl)-furan
  申请人：——

  公开号：US20030130529A1

  公开（公告）日：2003-07-10

  The present invention refers to a new procedure for obtaining and purifying 2-bromo-5-(2-bromo-2-nitrovinyl)-furan in one reaction step starting with 2-nitrovinylfuran, and maintains high indexes of purity and an appropriate yield. The process involves the direct bromination of 2-nitrovinylfuran using charcoal from the beginning of the reaction, followed by the neutralization and dehydrobromination using pyridine, and finally crystallizing and purifying the product obtained with ethanol and charcoal. With the new procedure it is possible to reduce the time of obtaining the final product, the reaction becomes endothermic instead of exothermic, which facilitates the work of the operators and allows for the scaling up of the reaction to superior levels. The process significantly decreases the amount of chemicals in the reaction, some of them with toxic properties. Also the environmental negative impact from the process is diminished as the emission of the bromine vapors and other substances to the environment are eliminated and the residual liquids are cut in half.

  本发明是指一种以 2-硝基乙烯基呋喃为原料，通过一个反应步骤获得和纯化 2-溴-5-(2-溴-2-硝基乙烯基)-呋喃，并保持高纯度指标和适当收率的新工艺。 该工艺包括在反应开始时使用木炭直接溴化 2-硝基乙烯基呋喃，然后使用吡啶中和并脱氢溴化，最后使用乙醇和木炭结晶并纯化得到的产物。 采用新工艺可以缩短获得最终产品的时间，反应由放热变为内热，从而方便了操作人员的工作，并使反应规模达到更高水平。 该工艺大大减少了反应中化学物质的用量，其中一些化学物质具有毒性。此外，由于消除了向环境排放溴蒸汽和其他物质，残留液体也减少了一半，该工艺对环境的负面影响也随之降低。
• 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.