N-(1-chloro-2,2,2-trifluoroethyl)-4-methylbenzenesulfonamide | 1308287-54-8

• 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: N-(1-chloro-2,2,2-trifluoroethyl)-4-methylbenzenesulfonamide
• CAS: 1308287-54-8
• 化学式: C₉H₉ClF₃NO₂S
• 分子量: 287.69
• InChiKey: OENVWFFDJSWCCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  54.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(1-chloro-2,2,2-trifluoroethyl)-4-methylbenzenesulfonamide 在 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 24.0h， 生成 methyl 4,4,4-trifluoro-2-ethyl-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：

  1,1,1-Trifluor-2-p-toluolsulfonamino-2-hydroxy-ethan 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到N-(1-chloro-2,2,2-trifluoroethyl)-4-methylbenzenesulfonamide
  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

• Pd(II)-Catalyzed Aminoacetoxylation of Alkenes Via Tether Formation
  作者：Thomas Rossolini、Ashis Das、Stefano Nicolai、Jérôme Waser

  DOI：10.1021/acs.orglett.2c01838

  日期：2022.7.22

  A Pd-catalyzed method based on the use of a molecular tether is described for olefin difunctionalization. Enabled by an easily introduced trifluoroacetaldehyde-derived tether, a simultaneous introduction of oxygen and nitrogen heteroatoms across unsaturated carbon–carbon bonds was achieved under oxidative conditions, most probably via high-valent Pd intermediates. Good yields and high diastereoselectivity

  描述了一种基于使用分子链的 Pd 催化方法用于烯烃双官能化。通过易于引入的三氟乙醛衍生系链，在氧化条件下，很可能通过高价 Pd 中间体实现了在不饱和碳-碳键上同时引入氧和氮杂原子。芳基取代烯烃获得了良好的收率和高非对映选择性，而非末端烷基取代的烯烃则产生了氮杂-Heck 产物。在温和条件下的系链断裂提供了对官能化 β-氨基醇的快速访问。
• 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.