(4S,6S)-6-[(2R)-3,3-dimethyl-γ-butyrolacton-2-yl]oxy-4-(4-methoxyphenyl)-2-phenyl-5,6-dihydro-4H-1,3-oxazine | 562099-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S,6S)-6-[(2R)-3,3-dimethyl-γ-butyrolacton-2-yl]oxy-4-(4-methoxyphenyl)-2-phenyl-5,6-dihydro-4H-1,3-oxazine
• 英文别名: (3R)-3-[[(4S,6S)-4-(4-methoxyphenyl)-2-phenyl-5,6-dihydro-4H-1,3-oxazin-6-yl]oxy]-4,4-dimethyloxolan-2-one
• CAS: 562099-98-3
• 化学式: C₂₃H₂₅NO₅
• 分子量: 395.455
• InChiKey: GKDQTVQIVZGGRD-UFYCRDLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,6S)-6-[(2R)-3,3-dimethyl-γ-butyrolacton-2-yl]oxy-4-(4-methoxyphenyl)-2-phenyl-5,6-dihydro-4H-1,3-oxazine 在 Amberlyst-15 H⁽¹⁺⁾ 作用下， 以 水 、 丙酮 为溶剂， 以40%的产率得到(3S)-3-benzamido-3-(4-methoxyphenyl)propanal
  参考文献：
  名称：

  Novel Use of N-Benzoyl-N,O-acetals as N-Acylimine Equivalents in Asymmetric Heterocycloaddition:  An Extended Enantioselective Pathway to β-Benzamido Aldehydes

  摘要：

  For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl4-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.

  DOI：

  10.1021/jo0203138
• 作为产物：
  描述：

  N-benzoyl-1-methoxy-1-(p-methoxyphenyl)-methylamine 在 tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium 作用下， 以 环己烷 、 甲苯 为溶剂， 反应 192.0h， 生成 (4S,6S)-6-[(2R)-3,3-dimethyl-γ-butyrolacton-2-yl]oxy-4-(4-methoxyphenyl)-2-phenyl-5,6-dihydro-4H-1,3-oxazine
  参考文献：
  名称：

  Novel Use of N-Benzoyl-N,O-acetals as N-Acylimine Equivalents in Asymmetric Heterocycloaddition:  An Extended Enantioselective Pathway to β-Benzamido Aldehydes

  摘要：

  For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl4-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.

  DOI：

  10.1021/jo0203138