2-(2-(甲硫基)乙炔基)苯甲腈 | 1012327-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-(甲硫基)乙炔基)苯甲腈
• 英文名称: methyl (2-cyanophenyl)ethynyl sulfide
• 英文别名: 2-(2-(methylthio)ethynyl)benzonitrile；2-(2-Methylsulfanylethynyl)benzonitrile
• CAS: 1012327-10-4
• 化学式: C₁₀H₇NS
• 分子量: 173.238
• InChiKey: AKGWFMBYSJOQSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-bromophenyl)-3,3-bis(methylthio)acrylonitrile 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以59%的产率得到2-(2-(甲硫基)乙炔基)苯甲腈
  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

• Synthesis of Thioalkynes by Desilylative Sonogashira Cross‐Coupling of Aryl Iodides and 1‐Methylthio‐2‐(trimethylsilyl)ethyne
  作者：Yang Cao、Yang Huang、Paul R. Blakemore

  DOI：10.1002/ejoc.202200498

  日期：2022.9.13

  An efficient and operationally straightforward synthesis of 1-methylthio-2-arylethyne derivatives is described based on a desilylative Sonogashira cross-coupling between aryl iodides and a silylated surrogate for methylthioacetylene (Me3SiCCSMe). Extension of the process to a selection of other thioether types is also documented.

  基于芳基碘化物和甲硫基乙炔 (Me 3 SiCCSMe)的甲硅烷基化替代物之间的脱甲硅烷基 Sonogashira 交叉偶联，描述了一种高效且操作简单的 1-甲硫基-2-芳基乙炔衍生物合成方法。还记录了将该过程扩展到选择其他硫醚类型。
• A Novel Anionic Domino Process for the Synthesis of <i>o</i>-Cyanoaryl-Methylthio/Alkyl/Aryl/Heteroaryl Acetylenes
  作者：Sarvesh Kumar、Saravanan Peruncheralathan、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1021/ol800029c

  日期：2008.3.1

  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.