(2-allyl-3,5-dimethylphenyl)(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfide | 1338723-53-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2-allyl-3,5-dimethylphenyl)(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfide
• 英文别名: 1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluorodecylsulfanyl)-3,5-dimethyl-2-prop-2-enylbenzene
• CAS: 1338723-53-7
• 化学式: C₂₁H₁₇F₁₇S
• 分子量: 624.405
• InChiKey: POYUVCKOXJBLNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (2-allyl-3,5-dimethylphenyl)(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfide 、 magnesium,2H-thiophen-2-ide,bromide 在 bis(triphenylphosphine)nickel(II) chloride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 24.0h， 以70%的产率得到2-(2-allyl-3,5-dimethylphenyl)thiophene
  参考文献：
  名称：

  NucleophilicOrthoAllylation of Aryl and Heteroaryl Sulfoxides

  摘要：

  Aryl and heteroaryl sulf oxides undergo ortho allylation upon treatment with Tf2O and allyisilanes. The method complements the use of sulfoxides to direct ortho-metalation and reaction with electrophiles as it allows allylic carbon nucleophiles to be added ortho to the directing group in a metal-free process. The versatile sulfide adducts can be selectively manipulated using various methods Including Kumada-Corriu cross-coupling of the organosulfanyl group.

  DOI：

  10.1021/ol2025197
• 作为产物：
  描述：

  3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟-1-癸硫醇 在 copper(l) iodide 、 三氟甲磺酸酐 、 potassium carbonate 、 乙二醇 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 26.0h， 生成 (2-allyl-3,5-dimethylphenyl)(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfide
  参考文献：
  名称：

  NucleophilicOrthoAllylation of Aryl and Heteroaryl Sulfoxides

  摘要：

  Aryl and heteroaryl sulf oxides undergo ortho allylation upon treatment with Tf2O and allyisilanes. The method complements the use of sulfoxides to direct ortho-metalation and reaction with electrophiles as it allows allylic carbon nucleophiles to be added ortho to the directing group in a metal-free process. The versatile sulfide adducts can be selectively manipulated using various methods Including Kumada-Corriu cross-coupling of the organosulfanyl group.

  DOI：

  10.1021/ol2025197

文献信息

• Nucleophilic<i>Ortho</i>Allylation of Aryl and Heteroaryl Sulfoxides
  作者：Andrew J. Eberhart、Jason E. Imbriglio、David J. Procter

  DOI：10.1021/ol2025197

  日期：2011.11.4

  Aryl and heteroaryl sulf oxides undergo ortho allylation upon treatment with Tf2O and allyisilanes. The method complements the use of sulfoxides to direct ortho-metalation and reaction with electrophiles as it allows allylic carbon nucleophiles to be added ortho to the directing group in a metal-free process. The versatile sulfide adducts can be selectively manipulated using various methods Including Kumada-Corriu cross-coupling of the organosulfanyl group.