N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide | 518358-52-6

• 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: N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide
• CAS: 518358-52-6
• 化学式: C₁₅H₂₃NO₄S
• 分子量: 313.418
• InChiKey: ATNFHXLPOCUSPN-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide 在 四甲基乙二胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-1-Phenyl-propane-2-sulfonic acid ((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-methyl-amide 、 (S)-1-Phenyl-propane-2-sulfonic acid ((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-methyl-amide
  参考文献：
  名称：

  Asymmetric Synthesis of -Substituted N-Methylsulfonamides

  摘要：

  A novel amine auxiliary for the asymmetric synthesis of a-substituted N-methylsulfonamides is described. The reaction of 4-([1,1'-biphenyl]-4-yl)-2,2-dimethyl-1,3-dioxan-5-amine (16) with various aliphatic sulfonyl chlorides afforded the corresponding sulfonamides, which were lithiated and subsequently reacted with electrophiles to give the corresponding products in high yields and good-to-excellent asymmetric inductions (de 83-95%). Racemization-free cleavage of the auxiliary led to the a-alkylated N-methylsulfonamides in acceptable yields and high enantiomer purities (ee 91 to greater than or equal to 98).

  DOI：

  10.1002/1522-2675(200211)85:11<3657::aid-hlca3657>3.0.co;2-a
• 作为产物：
  描述：

  (4S,5S)-2,2-二甲基-4-苯基-1,3-二恶烷-5-胺 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 生成 N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]-N-methylethanesulfonamide
  参考文献：
  名称：

  Asymmetric Synthesis of -Substituted N-Methylsulfonamides

  摘要：

  A novel amine auxiliary for the asymmetric synthesis of a-substituted N-methylsulfonamides is described. The reaction of 4-([1,1'-biphenyl]-4-yl)-2,2-dimethyl-1,3-dioxan-5-amine (16) with various aliphatic sulfonyl chlorides afforded the corresponding sulfonamides, which were lithiated and subsequently reacted with electrophiles to give the corresponding products in high yields and good-to-excellent asymmetric inductions (de 83-95%). Racemization-free cleavage of the auxiliary led to the a-alkylated N-methylsulfonamides in acceptable yields and high enantiomer purities (ee 91 to greater than or equal to 98).

  DOI：

  10.1002/1522-2675(200211)85:11<3657::aid-hlca3657>3.0.co;2-a