1,1,1-Trifluor-2-p-toluolsulfonamino-2-hydroxy-ethan | 10009-37-7

• 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: 1,1,1-Trifluor-2-p-toluolsulfonamino-2-hydroxy-ethan
• 英文别名: N-(1-hydroxy-2,2,2-trifluoroethyl)-4-methylbenzenesulfonamide；4-methyl-N-(2,2,2-trifluoro-1-hydroxyethyl)benzenesulfonamide
• CAS: 10009-37-7
• 化学式: C₉H₁₀F₃NO₃S
• 分子量: 269.245
• InChiKey: SYPQVSPNTIIDBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C
• 沸点：
  365.7±52.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1,1-Trifluor-2-p-toluolsulfonamino-2-hydroxy-ethan 在 氯化亚砜 、 sodium azide 、 二甲基十二/十四烷基叔胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 methyl 4,4,4-trifluoro-2-methyl-3-(4-methylphenylsulfonamido)butanoate
  参考文献：
  名称：

  Diastereoselective synthesis of trans-trifluoromethyl-β-lactams and α-alkyl-β-trifluoromethyl-β-amino esters

  摘要：

  The diastereoselective synthesis of beta-lactams was examined from N-tosyl-1-chloro-2,2,2-trifluoroethylamine 3 and various nonactivated aliphatic acid chlorides in the presence of a Bronsted base. The mild reaction conditions allowed to get trifluoromethyl-beta-lactams in good yields with high trans-diastereo selectivity. In addition, we also demonstrated that ring-opening of beta-lactams easily provided alpha-alkyl-beta-trifluoromethyl-beta-amino esters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.001
• 作为产物：
  描述：

  三氟乙醛缩甲基半醇 、 对甲苯磺酰胺 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以65%的产率得到1,1,1-Trifluor-2-p-toluolsulfonamino-2-hydroxy-ethan
  参考文献：
  名称：

  Diastereoselective synthesis of trans-trifluoromethyl-β-lactams and α-alkyl-β-trifluoromethyl-β-amino esters

  摘要：

  The diastereoselective synthesis of beta-lactams was examined from N-tosyl-1-chloro-2,2,2-trifluoroethylamine 3 and various nonactivated aliphatic acid chlorides in the presence of a Bronsted base. The mild reaction conditions allowed to get trifluoromethyl-beta-lactams in good yields with high trans-diastereo selectivity. In addition, we also demonstrated that ring-opening of beta-lactams easily provided alpha-alkyl-beta-trifluoromethyl-beta-amino esters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.001

文献信息

• Diastereoselective synthesis of trans-trifluoromethyl-β-lactams and α-alkyl-β-trifluoromethyl-β-amino esters
  作者：Vitaliy Petrik、Gerd-Volker Röschenthaler、Dominique Cahard

  DOI：10.1016/j.tet.2011.03.001

  日期：2011.5

  The diastereoselective synthesis of beta-lactams was examined from N-tosyl-1-chloro-2,2,2-trifluoroethylamine 3 and various nonactivated aliphatic acid chlorides in the presence of a Bronsted base. The mild reaction conditions allowed to get trifluoromethyl-beta-lactams in good yields with high trans-diastereo selectivity. In addition, we also demonstrated that ring-opening of beta-lactams easily provided alpha-alkyl-beta-trifluoromethyl-beta-amino esters. (C) 2011 Elsevier Ltd. All rights reserved.