4-[(2,4-Dimethyl)phenylsulfinyl]-2,3-dihydrofuran | 211310-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[(2,4-Dimethyl)phenylsulfinyl]-2,3-dihydrofuran
• 英文别名: 4-(2,4-Dimethylbenzene-1-sulfinyl)-2,3-dihydrofuran；4-(2,4-dimethylphenyl)sulfinyl-2,3-dihydrofuran
• CAS: 211310-22-4
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: YYIOFUXOWDGDRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘苯 、 4-[(2,4-Dimethyl)phenylsulfinyl]-2,3-dihydrofuran 在 palladium diacetate 1,3-双(二苯基膦)丙烷 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S*,SR*)-3-(2,4-Dimethylphenylsulfinyl)-2-phenyl-2,5-dihydrofuran 、 (2R*,SR*)-3-(2,4-Dimethylphenylsulfinyl)-2-phenyl-2,5-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：

  (2,4-dimethylphenyl)methylsulfoxide 在 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 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

文献信息

• Sulfinyl Group as a Novel Chiral Auxiliary in Asymmetric Heck Reactions
  作者：Nuria Díaz Buezo、Inés Alonso、Juan C. Carretero

  DOI：10.1021/ja980858c

  日期：1998.7.1
• Sulfoxides as Stereochemical Controllers in Intermolecular Heck Reactions
  作者：Nuria Díaz Buezo、Juan Carlos de la Rosa、Julián Priego、Inés Alonso、Juan Carlos Carretero

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

  日期：2001.9.17

  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.