4-ethyl-5-phenyl-5H-[1,2,3]oxathiazole 2,2-dioxide | 1380313-52-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-ethyl-5-phenyl-5H-[1,2,3]oxathiazole 2,2-dioxide
• 英文别名: 4-ethyl-5-phenyl-5H-oxathiazole 2,2-dioxide
• CAS: 1380313-52-9
• 化学式: C₁₀H₁₁NO₃S
• 分子量: 225.268
• InChiKey: AZDUEPXAPZBMCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-ethyl-5-phenyl-5H-[1,2,3]oxathiazole 2,2-dioxide 在 甲酸 、 RhCl[(R,R)-TsDPEN](C5Me5) 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 以79%的产率得到(4S,5R)-4-ethyl-5-phenyl-[1,2,3]oxathiazolidine 2,2-dioxide
  参考文献：
  名称：

  Stereoselective Synthesis of Norephedrine and Norpseudoephedrine by Using Asymmetric Transfer Hydrogenation Accompanied by Dynamic Kinetic Resolution

  摘要：

  Each of the enantiomers of both norephedrine and norpseudoephedrine were stereoselectively prepared from the common, prochiral cyclic sulfamidate imine of racemic 1-hydroxy-1-phenyl-propan-2-one by employing asymmetric transfer hydrogenation (ATH) catalyzed by the well-defined chiral Rh-complexes, (S,S)- or (R,R)-Cp*RhCl(TsDPEN), and HCO2H/Et3N as the hydrogen source. The ATH processes are carried out under mild conditions (rt, 15 min) and are accompanied by dynamic kinetic resolution.

  DOI：

  10.1021/jo300867y
• 作为产物：
  描述：

  1-hydroxy-1-phenylbutan-2-one 在 氨基磺酰氯 、 对甲苯磺酸 作用下， 以 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 1.5h， 生成 4-ethyl-5-phenyl-5H-[1,2,3]oxathiazole 2,2-dioxide
  参考文献：
  名称：

  Stereoselective Synthesis of Norephedrine and Norpseudoephedrine by Using Asymmetric Transfer Hydrogenation Accompanied by Dynamic Kinetic Resolution

  摘要：

  Each of the enantiomers of both norephedrine and norpseudoephedrine were stereoselectively prepared from the common, prochiral cyclic sulfamidate imine of racemic 1-hydroxy-1-phenyl-propan-2-one by employing asymmetric transfer hydrogenation (ATH) catalyzed by the well-defined chiral Rh-complexes, (S,S)- or (R,R)-Cp*RhCl(TsDPEN), and HCO2H/Et3N as the hydrogen source. The ATH processes are carried out under mild conditions (rt, 15 min) and are accompanied by dynamic kinetic resolution.

  DOI：

  10.1021/jo300867y