2-(2-bromo-4,5-dimethoxyphenyl)-3-(3-methoxyphenyl)-3-(methylthio)acrylonitrile | 1012327-17-1

• 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-bromo-4,5-dimethoxyphenyl)-3-(3-methoxyphenyl)-3-(methylthio)acrylonitrile
• CAS: 1012327-17-1
• 化学式: C₁₉H₁₈BrNO₃S
• 分子量: 420.327
• InChiKey: DFNXXBDBVSYKCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  51.48
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-4,5-dimethoxyphenyl)-3-(3-methoxyphenyl)-3-(methylthio)acrylonitrile 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以61%的产率得到4,5-dimethoxy-2-(2-(3-methoxyphenyl)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：

  2-溴-4,5-二甲氧基苯乙腈 、 methyl (m-methoxyphenyl)carbodithioate 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以85%的产率得到2-(2-bromo-4,5-dimethoxyphenyl)-3-(3-methoxyphenyl)-3-(methylthio)acrylonitrile
  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

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。