N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]ethanesulfonamide | 518358-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]ethanesulfonamide
• CAS: 518358-51-5
• 化学式: C₁₄H₂₁NO₄S
• 分子量: 299.391
• InChiKey: UVPXUVUCKCOZKH-STQMWFEESA-N

物化性质

• 沸点：
  424.5±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]ethanesulfonamide 在 正丁基锂 、 四甲基乙二胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (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：

  乙基磺酰氯 、 (4S,5S)-2,2-二甲基-4-苯基-1,3-二恶烷-5-胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]ethanesulfonamide
  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