2-fluoro-3,3-bis(methylthio)acrylonitrile | 151607-51-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-fluoro-3,3-bis(methylthio)acrylonitrile
• 英文别名: 3,3-Bis(methylthio)-2-fluoroacrylonitrile；2-Fluoro-3,3-bis(methyl-thio)acrylonitrile；2-fluoro-3,3-bis(methylsulfanyl)prop-2-enenitrile
• CAS: 151607-51-1
• 化学式: C₅H₆FNS₂
• 分子量: 163.24
• InChiKey: JATZJUMCRCBRCD-UHFFFAOYSA-N

物化性质

• 沸点：
  190.0±40.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-fluoro-3,3-bis(methylthio)acrylonitrile 在 乙基溴化镁 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1,1-Bis(methylthio)-2-fluoroprop-1-en-3-ol
  参考文献：
  名称：

  Methods for the stereoselective synthesis of 2-fluoroalkenoates. Carbonyl condensation reactions of 3,3-bis(methylthio)-2-fluoropropenal, a highly-functionalized fluoroacrylate cation equivalent

  摘要：

  New methodology for the preparation of 2-fluoroacrylates has been developed on the basis of the reagent 3,3-bis(methylthio)-2-fluoropropenal. This highly-functionalized aldehyde is prepared by the condensation of carbon disulfide with fluoroacetonitrile followed by reduction of the nitrile. It is subjected to nucleophilic addition with organometallic reagents and enolates to yield allylic alcohol products that can be rearranged under acidic conditions to (Z)-2-fluoroacrylate thioesters. Other desired fluoroacrylates are also available via conventional fluorinated Homer-Wadsworth-Emmons or Reformatsky reagents.

  DOI：

  10.1021/jo00073a029
• 作为产物：
  描述：

  二硫化碳 、 氟乙腈 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 以66%的产率得到2-fluoro-3,3-bis(methylthio)acrylonitrile
  参考文献：
  名称：

  Methods for the stereoselective synthesis of 2-fluoroalkenoates. Carbonyl condensation reactions of 3,3-bis(methylthio)-2-fluoropropenal, a highly-functionalized fluoroacrylate cation equivalent

  摘要：

  New methodology for the preparation of 2-fluoroacrylates has been developed on the basis of the reagent 3,3-bis(methylthio)-2-fluoropropenal. This highly-functionalized aldehyde is prepared by the condensation of carbon disulfide with fluoroacetonitrile followed by reduction of the nitrile. It is subjected to nucleophilic addition with organometallic reagents and enolates to yield allylic alcohol products that can be rearranged under acidic conditions to (Z)-2-fluoroacrylate thioesters. Other desired fluoroacrylates are also available via conventional fluorinated Homer-Wadsworth-Emmons or Reformatsky reagents.

  DOI：

  10.1021/jo00073a029

文献信息

• ——
  作者：A. N. Kovregin、A. Yu. Sizov、A. F. Ermolov

  DOI：10.1023/a:1011325520421

  日期：——

  A new method was developed for the synthesis of fluorine-containing functionally substituted vinyl sulfides and ketene dithioacetals from the corresponding derivatives of a-trifluoromethyl-substituted CH-acids and thiols in the presence of BF(3) . NEt(3).
• Methods for the stereoselective synthesis of 2-fluoroalkenoates. Carbonyl condensation reactions of 3,3-bis(methylthio)-2-fluoropropenal, a highly-functionalized fluoroacrylate cation equivalent
  作者：Michael C. Pirrung、Elizabeth G. Rowley、Christopher P. Holmes

  DOI：10.1021/jo00073a029

  日期：1993.10

  New methodology for the preparation of 2-fluoroacrylates has been developed on the basis of the reagent 3,3-bis(methylthio)-2-fluoropropenal. This highly-functionalized aldehyde is prepared by the condensation of carbon disulfide with fluoroacetonitrile followed by reduction of the nitrile. It is subjected to nucleophilic addition with organometallic reagents and enolates to yield allylic alcohol products that can be rearranged under acidic conditions to (Z)-2-fluoroacrylate thioesters. Other desired fluoroacrylates are also available via conventional fluorinated Homer-Wadsworth-Emmons or Reformatsky reagents.