4-tert-butyl-N-(2-chloro-2-phenylethyl)benzenesulfonamide | 1202798-51-3

• 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-tert-butyl-N-(2-chloro-2-phenylethyl)benzenesulfonamide
• CAS: 1202798-51-3
• 化学式: C₁₈H₂₂ClNO₂S
• 分子量: 351.897
• InChiKey: LJEBATZLTXIPFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• 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：
  3

反应信息

• 作为产物：
  描述：

  1-((4-(tert-butyl)phenyl)sulfonyl)-2-phenylaziridine 在 三氟化硼乙醚 、 苄基三乙基氯化铵 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以95%的产率得到4-tert-butyl-N-(2-chloro-2-phenylethyl)benzenesulfonamide
  参考文献：
  名称：

  BF₃·OEt₂-Mediated Highly Regioselective S_N2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides

  摘要：

  A highly regioselective Lewis acid-mediated S(N)2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH2Cl2 solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed. The mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines with excellent er and dr. Chloroamines obtained from 2,3-disubstituted aziridines were converted to the chiral N-tosylamines via radical dehalogenation.

  DOI：

  10.1021/jo902244y

文献信息

• Catalytic Asymmetric Ring Openings of Meso and Terminal Aziridines with Halides Mediated by Chiral 1,2,3-Triazolium Silicates
  作者：Kohsuke Ohmatsu、Yuta Hamajima、Takashi Ooi

  DOI：10.1021/ja3028668

  日期：2012.5.30

  Catalytic asymmetric chloride and bromide ring openings of meso aziridines with trimethylsilyl halides have been developed using modular chiral 1,2,3-triazolium chlorides as catalysts. Control experiments suggest the reaction pathway involving hypervalent silicate ions as reactive intermediates. The application of this system to the efficient kinetic resolution of terminal aziridines is also reported.