3,3-Bis(methylthio)-2-fluoropropenal | 151607-52-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 3,3-Bis(methylthio)-2-fluoropropenal
• 英文别名: 2-Fluoro-3,3-bis(methylsulfanyl)prop-2-enal
• CAS: 151607-52-2
• 化学式: C₅H₇FOS₂
• 分子量: 166.24
• InChiKey: HDEXNEZQSAFOSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-Bis(methylthio)-2-fluoropropenal 在 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 生成 5,5-Bis(methylthio)-4-fluoropenta-2,4-dienoic acid
  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：

  2-fluoro-3,3-bis(methylthio)acrylonitrile 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到3,3-Bis(methylthio)-2-fluoropropenal
  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

• 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.