pentachlorophenyl 3-chloropropyl sulfide | 1227176-31-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: pentachlorophenyl 3-chloropropyl sulfide
• CAS: 1227176-31-9
• 化学式: C₉H₆Cl₆S
• 分子量: 358.931
• InChiKey: DRTIOIGCKKDKQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  pentachlorophenyl 3-chloropropyl sulfide 在 水 、 溴 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 为溶剂， 以13%的产率得到pentachlorophenyl 3-chloropropyl sulfoxide
  参考文献：
  名称：

  Diastereoselective Synthesis of Tetrahydrofurans from Aryl 3-Chloropropylsulfoxides and Aldehydes

  摘要：

  Carbanions of aryl 3-chloropropylsulfoxides react with nonenolizable aldehydes to give 2,3-disubstituted tetrahydrofurans. Deprotonation of the sulfoxides carried out in the presence of aldehydes results in the addition of the carbanions to the carbonyl group of the aldehydes, followed by 1,5-intra-molecular substitution of the resulting aldol-type anion to produce the tetrahydrofuran ring. The 2-aryl and 3-arylsulfinyl substituents are always in trans relation, and the reaction proceeds with high diastereoselectivity also in respect to the chiral sulfur atom. The diastereoselectivity is attributed to the cyclic transition state of the aldol addition and increases when the aromatic ring of the sulfoxide contains electron-withdrawing substituents, whereas that of the aldehyde has eleetron-donatine groups.

  DOI：

  10.1021/jo1002196
• 作为产物：
  描述：

  五氯苯硫酚 、 1-溴-3-氯丙烷 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以68%的产率得到pentachlorophenyl 3-chloropropyl sulfide
  参考文献：
  名称：

  Diastereoselective Synthesis of Tetrahydrofurans from Aryl 3-Chloropropylsulfoxides and Aldehydes

  摘要：

  Carbanions of aryl 3-chloropropylsulfoxides react with nonenolizable aldehydes to give 2,3-disubstituted tetrahydrofurans. Deprotonation of the sulfoxides carried out in the presence of aldehydes results in the addition of the carbanions to the carbonyl group of the aldehydes, followed by 1,5-intra-molecular substitution of the resulting aldol-type anion to produce the tetrahydrofuran ring. The 2-aryl and 3-arylsulfinyl substituents are always in trans relation, and the reaction proceeds with high diastereoselectivity also in respect to the chiral sulfur atom. The diastereoselectivity is attributed to the cyclic transition state of the aldol addition and increases when the aromatic ring of the sulfoxide contains electron-withdrawing substituents, whereas that of the aldehyde has eleetron-donatine groups.

  DOI：

  10.1021/jo1002196