2-(2-bromophenyl)-3-(furan-2-yl)-3-(methylthio)acrylonitrile | 1012327-25-1

• 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: 2-(2-bromophenyl)-3-(furan-2-yl)-3-(methylthio)acrylonitrile
• 英文别名: 2-(2-bromophenyl)-3-(furan-2-yl)-3-methylsulfanylprop-2-enenitrile
• CAS: 1012327-25-1
• 化学式: C₁₄H₁₀BrNOS
• 分子量: 320.209
• InChiKey: DQYUNNNAEGTQEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  36.93
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenyl)-3-(furan-2-yl)-3-(methylthio)acrylonitrile 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以100%的产率得到2-(2-(furan-2-yl)ethynyl)benzonitrile
  参考文献：
  名称：

  A Novel Anionic Domino Process for the Synthesis of o-Cyanoaryl-Methylthio/Alkyl/Aryl/Heteroaryl Acetylenes

  摘要：

  A novel unexpected anionic domino process involving n-BuLi-induced rearrangement of 3,3-bis(methylthio) or 3-methylthio-3-aryl/heteroaryl/alkyl-o-bromoarylacrylonitriles to o-cyanoarylacetylenes in synthetically useful yields has been reported. The scope and generality of the reaction has been examined, and a possible mechanism has been proposed.

  DOI：

  10.1021/ol800029c
• 作为产物：
  描述：

  furan-2-carbodithioic acid 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2-bromophenyl)-3-(furan-2-yl)-3-(methylthio)acrylonitrile
  参考文献：
  名称：

  Synthesis of N-Functionalized/NH-Multisubstituted Indoles, Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via Sequential One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular Amination of 2-[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles

  摘要：

  A novel, efficient route to substituted 1-N-(het)aryl/NH-2-(het)aryl-3-cyanoindoles and related pyrrolo-fused heterocycles such as thienopyrroles, pyrroloindoles, and pyrazolopyrroles has been reported. The overall protocol involves sequential cycloamination of readily available 2-[2-bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitrile precursors with primary amines or amides via two key C-N bond-forming processes, one base-mediated intermolecular and the other Cu-catalyzed intramolecular arylamination leading to N(1)-C(2) and N(1)-C(7a) bond formation, respectively, in a two-step one-pot procedure.

  DOI：

  10.1021/jo501114a

文献信息

• Novel Route to 2,3-Substituted Benzo[<i>b</i>]thiophenes via Intramolecular Radical Cyclization
  作者：Prabal P. Singh、A. K. Yadav、H. Ila、H. Junjappa

  DOI：10.1021/jo900615p

  日期：2009.8.7

  A novel route to 2,3-substituted benzo[b]thiophenes by intramolecular radical cyclization of polarized ketene dithioacetals derived from o-bromoarylacetonitriles or the corresponding 3-(methylthio)-3-alkyl/aryl/heteroaryl analogues has been reported.

  已经报道了通过衍生自邻-溴芳基乙腈或相应的3-（甲硫基）-3-烷基/芳基/杂芳基类似物的极化的烯酮二硫缩醛的分子内自由基环化形成2，3-取代的苯并[ b ]噻吩的新途径。