O-ethyl-S-(4-chlorophenylthio)difluoromethyl xanthate | 1563062-31-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: O-ethyl-S-(4-chlorophenylthio)difluoromethyl xanthate
• 英文别名: S-{[(4-Chlorophenyl)sulfanyl](difluoro)methyl} O-ethyl carbonodithioate；O-ethyl [(4-chlorophenyl)sulfanyl-difluoromethyl]sulfanylmethanethioate
• CAS: 1563062-31-6
• 化学式: C₁₀H₉ClF₂OS₃
• 分子量: 314.829
• InChiKey: KHBNIVKWPJEJRX-UHFFFAOYSA-N

物化性质

• 沸点：
  302.0±42.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  91.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-ethyl-S-(4-chlorophenylthio)difluoromethyl xanthate 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成 ethyl 1-[(6-chloro-2,2-difluoro-3,4-dihydro-2H-1-benzothiopyran-4-yl)methyl]-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  A Convergent Route to Geminal Difluorosulfides and to Functionalized Difluorothiochromans, a New Family of Organofluorine Compounds

  摘要：

  The synthesis of the novel O-ethyl-S-(4-chlorophenylthio)difluoromethyl xanthate and its radical addition to various terminal alkenes are described. The geminal difluorosulfide adducts undergo closure onto the aromatic ring by further treatment with peroxide to furnish difluorothiochromans, a new family of organofluorine compounds.

  DOI：

  10.1021/ol5002939
• 作为产物：
  描述：

  苯硫醇,4-氯-,盐钠 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 环己烷 为溶剂， 反应 22.0h， 生成 O-ethyl-S-(4-chlorophenylthio)difluoromethyl xanthate
  参考文献：
  名称：

  A Convergent Route to Geminal Difluorosulfides and to Functionalized Difluorothiochromans, a New Family of Organofluorine Compounds

  摘要：

  The synthesis of the novel O-ethyl-S-(4-chlorophenylthio)difluoromethyl xanthate and its radical addition to various terminal alkenes are described. The geminal difluorosulfide adducts undergo closure onto the aromatic ring by further treatment with peroxide to furnish difluorothiochromans, a new family of organofluorine compounds.

  DOI：

  10.1021/ol5002939

文献信息

• Radical Instability in Aid of Efficiency: A Powerful Route to Highly Functional MIDA Boronates
  作者：Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/jacs.5b03893

  日期：2015.6.3

  The inability of the sp(3) boron in MIDA boronates to stabilize an adjacent radical makes possible the efficient addition of a wide array Of xanthates to vinyl MIDA boronate, leading to highly functionalized and diverse aliphatic organoboron structures. The lack of radical Stabilization also allows the exchange Of the Xanthate in the adducts with a bromine. In one case, the bromine was substituted to generate a cyclopropyl MIDA derivative.