(Z)-2-(2-bromo-2-nitrovinyl)thiophene | 960211-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (Z)-2-(2-bromo-2-nitrovinyl)thiophene
• 英文别名: 2-[(Z)-2-bromo-2-nitroethenyl]thiophene
• CAS: 960211-66-9
• 化学式: C₆H₄BrNO₂S
• 分子量: 234.073
• InChiKey: JYGXMCYINDKUJY-GQCTYLIASA-N

物化性质

• 熔点：
  92-94 °C(Solv: ethyl ether (60-29-7); heptane (142-82-5))
• 沸点：
  296.8±30.0 °C(Predicted)
• 密度：
  1.812±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 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：
  74.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-(2-bromo-2-nitrovinyl)thiophene 、 1-辛炔 在 四(三苯基膦)钯 N-甲基吗啉 、 copper(l) iodide 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以86%的产率得到(E)-2-(2-nitrodec-1-en-3-ynyl)thiophene
  参考文献：
  名称：

  Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes

  摘要：

  (Z)-alpha-Bromo-beta-substituted nitroethylenes undergo facile Suzuki coupling with aryl, heteroaryl, and vinylboronic acids in the presence of Pd(PPh3)(4) as catalyst to afford (E)-alpha,beta-disubstituted nitroethylenes in high yield (up to 95%) and complete specificity. Similar coupling of alpha-bromonitroethylenes with terminal acetylenes (Sonogashira coupling) provides a novel route to (E)-nitroenynes. These Pd-catalyzed coupling methods offer a convenient and stereospecific entry into a diverse array of synthetically and biologically useful alpha,beta-disubstituted nitroethylenes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.012
• 作为产物：
  描述：

  2-(1,2-Dibromo-2-nitroethyl)thiophene 生成 (Z)-2-(2-bromo-2-nitrovinyl)thiophene
  参考文献：
  名称：

  VATANABEH, MITIO

  摘要：

  DOI：

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。
• VATANABEH, MITIO
  作者：VATANABEH, MITIO

  DOI：——

  日期：——
• A NEW INDUSTRIAL ANTIMICROBIAL: USES FOR 2-(2-BROMO-2-NITROETHENYL)-FURAN AND A NEW PROCESS OF FORMING 2-(2-BROMO-2-NITROETHENYL)-FURAN
  申请人：GREAT LAKES CHEMICAL CORPORATION

  公开号：EP0382812B1

  公开（公告）日：1993-11-03
• Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes
  作者：Madhu Ganesh、Irishi N.N. Namboothiri

  DOI：10.1016/j.tet.2007.09.012

  日期：2007.11

  (Z)-alpha-Bromo-beta-substituted nitroethylenes undergo facile Suzuki coupling with aryl, heteroaryl, and vinylboronic acids in the presence of Pd(PPh3)(4) as catalyst to afford (E)-alpha,beta-disubstituted nitroethylenes in high yield (up to 95%) and complete specificity. Similar coupling of alpha-bromonitroethylenes with terminal acetylenes (Sonogashira coupling) provides a novel route to (E)-nitroenynes. These Pd-catalyzed coupling methods offer a convenient and stereospecific entry into a diverse array of synthetically and biologically useful alpha,beta-disubstituted nitroethylenes. (c) 2007 Elsevier Ltd. All rights reserved.