(R)-1-hydroxymethyl-4-(p-tolyl)-2-azetidinone | 402828-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (R)-1-hydroxymethyl-4-(p-tolyl)-2-azetidinone
• 英文别名: (4R)-1-(hydroxymethyl)-4-(4-methylphenyl)azetidin-2-one
• CAS: 402828-09-5
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: CMJDLIWIAGXDQP-SNVBAGLBSA-N

物化性质

• 沸点：
  393.8±42.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙醇 、 (R)-1-hydroxymethyl-4-(p-tolyl)-2-azetidinone 在 盐酸 作用下， 反应 5.0h， 以54%的产率得到ethyl (3S)-3-amino-3-(4-methylphenyl)propanoate;hydrochloride
  参考文献：
  名称：

  Synthesis of 4-aryl-substituted β-lactam enantiomers by enzyme-catalyzed kinetic resolution

  摘要：

  Enantiopure 4-phenyl- and 4-(p-tolyl)-2-azetidinones 3a, 3b, 4a and 4b (with e.e.s of greater than or equal to 96%) were prepared through lipase-catalyzed asymmetric butyrylation of the primary OH group of N-hydroxymethylated beta -lactams (+/-)-5 and (+/-)-6 at the (R)-stereogenic centre or by lipase-catalyzed asymmetric debutyrylation of O-butyryloxymethyl-2-azetidinones (+/-)-7 and (+/-)-8 at the (R)-stereogenic centre. The ring-opening of lactams 5a. 5b, 6b and 8a with HCl/EtOH afforded the corresponding P-amino ester enantiomers 9a, 9b, 10a and 10b with e.e.s or greater than or equal to 92%, (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00388-3
• 作为产物：
  描述：

  4-(4-甲基苯基)氮杂环丁烷-2-酮 在 Lipase PS 、 乙醇 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醚 为溶剂， 反应 11.0h， 生成 (R)-1-hydroxymethyl-4-(p-tolyl)-2-azetidinone
  参考文献：
  名称：

  Synthesis of 4-aryl-substituted β-lactam enantiomers by enzyme-catalyzed kinetic resolution

  摘要：

  Enantiopure 4-phenyl- and 4-(p-tolyl)-2-azetidinones 3a, 3b, 4a and 4b (with e.e.s of greater than or equal to 96%) were prepared through lipase-catalyzed asymmetric butyrylation of the primary OH group of N-hydroxymethylated beta -lactams (+/-)-5 and (+/-)-6 at the (R)-stereogenic centre or by lipase-catalyzed asymmetric debutyrylation of O-butyryloxymethyl-2-azetidinones (+/-)-7 and (+/-)-8 at the (R)-stereogenic centre. The ring-opening of lactams 5a. 5b, 6b and 8a with HCl/EtOH afforded the corresponding P-amino ester enantiomers 9a, 9b, 10a and 10b with e.e.s or greater than or equal to 92%, (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00388-3

文献信息

• Synthesis of 4-aryl-substituted β-lactam enantiomers by enzyme-catalyzed kinetic resolution
  作者：Enikő Forró、Ferenc Fülöp

  DOI：10.1016/s0957-4166(01)00388-3

  日期：2001.9

  Enantiopure 4-phenyl- and 4-(p-tolyl)-2-azetidinones 3a, 3b, 4a and 4b (with e.e.s of greater than or equal to 96%) were prepared through lipase-catalyzed asymmetric butyrylation of the primary OH group of N-hydroxymethylated beta -lactams (+/-)-5 and (+/-)-6 at the (R)-stereogenic centre or by lipase-catalyzed asymmetric debutyrylation of O-butyryloxymethyl-2-azetidinones (+/-)-7 and (+/-)-8 at the (R)-stereogenic centre. The ring-opening of lactams 5a. 5b, 6b and 8a with HCl/EtOH afforded the corresponding P-amino ester enantiomers 9a, 9b, 10a and 10b with e.e.s or greater than or equal to 92%, (C) 2001 Elsevier Science Ltd. All rights reserved.