tert-butyl((4-(trifluoromethyl)phenyl)ethynyl)sulfane | 1612219-27-8

• 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: tert-butyl((4-(trifluoromethyl)phenyl)ethynyl)sulfane
• 英文别名: 1-(tert-Butylthio)-2-[4-(trifluoromethyl)phenyl]ethyne；1-(2-tert-butylsulfanylethynyl)-4-(trifluoromethyl)benzene
• CAS: 1612219-27-8
• 化学式: C₁₃H₁₃F₃S
• 分子量: 258.307
• InChiKey: SZRFGNVNYCADCF-UHFFFAOYSA-N

物化性质

• 沸点：
  285.5±50.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  、 叔丁基硫醇 在 potassium hydride 、 二甲胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以62%的产率得到tert-butyl((4-(trifluoromethyl)phenyl)ethynyl)sulfane
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Ynol Ethers and Thioynol Ethers via Displacement at sp Centers: A Revised Mechanistic Pathway

  摘要：

  We present here valuable extensions to our previous work in preparing highly functionalized, heteroatom-substituted alkynes via displacement at an sp center. Our results show that a wide range of ynol ethers can be prepared by the same methodology and that the same protocol can be applied to the synthesis of synthetically useful thioynol ethers. We also present new observations that have led us to revise our original hypothesis in favor of a pathway involving radical intermediates.

  DOI：

  10.1021/jo500814y

文献信息

• An improved transition-metal-free synthesis of aryl alkynyl sulfides via substitution of a halide at an sp-centre
  作者：Roomi Mohima Chowdhury、Jonathan D. Wilden

  DOI：10.1039/c5ob00494b

  日期：——

  A simple high-yielding preparation of aryl alkynyl sulfides is presented. The reaction of a chloroacetylene with a thiolate salt in the presence of an amine mediator (dimethylamine or N,N′-dimethylethylenediamine) yields the alkynyl sulfides in excellent yields. The alkynyl chloride is easily prepared from the parent alkyne.

  一种简单高产率的芳基炔基硫醚的制备方法被提出。在胺介质（二甲胺或N,N'-二甲基乙二胺）存在下，氯代乙炔与硫醇盐反应可高产率地生成炔基硫醚。炔基氯化物可从母体炔烃轻松制备。
• Transition-Metal-Free Synthesis of Ynol Ethers and Thioynol Ethers via Displacement at sp Centers: A Revised Mechanistic Pathway
  作者：Vincent James Gray、James Cuthbertson、Jonathan D. Wilden

  DOI：10.1021/jo500814y

  日期：2014.6.20

  We present here valuable extensions to our previous work in preparing highly functionalized, heteroatom-substituted alkynes via displacement at an sp center. Our results show that a wide range of ynol ethers can be prepared by the same methodology and that the same protocol can be applied to the synthesis of synthetically useful thioynol ethers. We also present new observations that have led us to revise our original hypothesis in favor of a pathway involving radical intermediates.