2-丙醇,1-氯-1,1-二氟-3-[(R)-(4-甲基苯基)亚硫酰基]-,(2R)- | 121898-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-丙醇,1-氯-1,1-二氟-3-[(R)-(4-甲基苯基)亚硫酰基]-,(2R)-
• 英文名称: (R)-1-Chloro-1,1-difluoro-3-((R)-toluene-4-sulfinyl)-propan-2-ol
• 英文别名: (2R)-1-chloro-1,1-difluoro-3-[(R)-(4-methylphenyl)sulfinyl]propan-2-ol
• CAS: 121898-09-7
• 化学式: C₁₀H₁₁ClF₂O₂S
• 分子量: 268.712
• InChiKey: LIFIWZRPHFATPW-JDNHERCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-chloro-1,1-difluoro-3-[(R)-(4-methylphenyl)sulfinyl]propan-2-one 在 ammonium hydroxide 、 锂硼氢 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 2-丙醇,1-氯-1,1-二氟-3-[(R)-(4-甲基苯基)亚硫酰基]-,(2R)- 、 (S)-1-Chloro-1,1-difluoro-3-((R)-toluene-4-sulfinyl)-propan-2-ol
  参考文献：
  名称：

  Homochiral Perfluoroalkyl-Group-Substituted Secondary Alcohols Through Stereoselective Reduction of Perfluoroalkyl 1-(p-Tolylsulfinyl)alkyl Ketones

  摘要：

  对某些对映纯的全氟烷基 α-(对甲苯亚磺酰基)酮进行了还原。当亚磺酰基碳上存在苯基残基时，含有全氟烷基和对甲苯亚磺酰基的醇类具有高立体选择性，而在其他情况下具有较低立体选择性。从单一非对映异构体中去除手性亚磺酰基，得到含有全氟烷基的对映纯的仲醇。

  DOI：

  10.1055/s-1988-27764

文献信息

• Stereoselection Parameters and Theoretical Model in the Enantioselective Protonation of Enolates with α-Sulfinyl Alcohols
  作者：Gregorio Asensio、Pedro Aleman、Jesus Gil、Luis R. Domingo、Mercedes Medio-Simon

  DOI：10.1021/jo981294y

  日期：1998.12.1

  The effects of the solvent, temperature, presence of Lithium salts in the medium, and acidity of the proton source on enantioselective protonation with alpha-sulfinyl alcohols 2a-e were studied. Stereoselectivity was generally enhanced when lithium bromide was present in the medium during enolization and also with the use of methylene chloride solutions. Conversely, the optimal reaction temperature varied with the alpha-sulfinyl alcohol used as a proton source, and its effect appears to be related to both the acidity of the proton source and the enolate structure. alpha-Sulfinyl alcohols 2a and 2b gave the best results when the reactions were carried out at -100 degrees C, while the optimal temperature with 2c was -78 degrees C. The same ee values were obtained with 2d and 2e at either -100 or -78 degrees C. In addition, an efficient synthesis of alpha-sulfinyl alcohols 2b and 2e is described.
• Homochiral Perfluoroalkyl-Group-Substituted Secondary Alcohols Through Stereoselective Reduction of Perfluoroalkyl 1-(<i>p</i>-Tolylsulfinyl)alkyl Ketones
  作者：Pierfrancesco Bravo、Massimo Frigerio、Giuseppe Resnati

  DOI：10.1055/s-1988-27764

  日期：——

  The reduction of some enantiomerically pure perfluoroalkyl α-(p-tolylsulfinyl) ketones was performed. Alcohols containing perfluoroalkyl and p-tolylsulfinyl groups were obtained with high diastereoselection when a phenyl residue was present on the sulfinylated carbon and with lower diastereoselection in the other cases. Removal of the chiral sulfinyl group from single diastereoisomers gave secondary alcohols containing a perfluoroalkyl group in enantiomerically pure form.

  对某些对映纯的全氟烷基 α-(对甲苯亚磺酰基)酮进行了还原。当亚磺酰基碳上存在苯基残基时，含有全氟烷基和对甲苯亚磺酰基的醇类具有高立体选择性，而在其他情况下具有较低立体选择性。从单一非对映异构体中去除手性亚磺酰基，得到含有全氟烷基的对映纯的仲醇。