4-((2,4-dimethylphenyl)thio)-2,3-dihydrofuran | 211310-46-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-((2,4-dimethylphenyl)thio)-2,3-dihydrofuran
• CAS: 211310-46-2
• 化学式: C₁₂H₁₄OS
• 分子量: 206.309
• InChiKey: RZLQMYPDPWHRFN-UHFFFAOYSA-N

物化性质

• 沸点：
  301.364±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.130±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-((2,4-dimethylphenyl)thio)-2,3-dihydrofuran 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到4-[(2,4-Dimethyl)phenylsulfinyl]-2,3-dihydrofuran
  参考文献：
  名称：

  Sulfoxides as Stereochemical Controllers in Intermolecular Heck Reactions

  摘要：

  The study of a variety of substituted sulfoxides as chiral auxiliaries in intermolecular Heck reactions of sulfinyldihydrofurans and sulfinylcyclopentenes with different iodoarenes is reported. In the presence of [Pd(OAc)(2)]/Ag2CO3 and a bidentate phosphine ligand, synthetically useful yields and asymmetric inductions were obtained. By far the best diastereoselectivities were obtained by the use of the palladium-coordinating o-(N,N-dimethylamino)phenylsulfinyl group. By final removal of the chiral auxiliary, these sulfoxide-stereocontrolled asymmetric Heck processes were applied to the enantioselective synthesis of 1-aryl-substituted and 1,3-diaryl-substituted dihydrofurans and cyclopentenes.

  DOI：

  10.1002/1521-3765(20010917)7:18<3890::aid-chem3890>3.0.co;2-y
• 作为产物：
  描述：

  2,3-二氢呋喃 、 (2,4-dimethylphenyl)methylsulfoxide 在 三氟乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以65%的产率得到4-((2,4-dimethylphenyl)thio)-2,3-dihydrofuran
  参考文献：
  名称：

  Sulfoxides as Stereochemical Controllers in Intermolecular Heck Reactions

  摘要：

  The study of a variety of substituted sulfoxides as chiral auxiliaries in intermolecular Heck reactions of sulfinyldihydrofurans and sulfinylcyclopentenes with different iodoarenes is reported. In the presence of [Pd(OAc)(2)]/Ag2CO3 and a bidentate phosphine ligand, synthetically useful yields and asymmetric inductions were obtained. By far the best diastereoselectivities were obtained by the use of the palladium-coordinating o-(N,N-dimethylamino)phenylsulfinyl group. By final removal of the chiral auxiliary, these sulfoxide-stereocontrolled asymmetric Heck processes were applied to the enantioselective synthesis of 1-aryl-substituted and 1,3-diaryl-substituted dihydrofurans and cyclopentenes.

  DOI：

  10.1002/1521-3765(20010917)7:18<3890::aid-chem3890>3.0.co;2-y