(S)-1-hydroxymethyl-4-phenyl-2-azetidinone | 402828-07-3

• 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: (S)-1-hydroxymethyl-4-phenyl-2-azetidinone
• 英文别名: (4S)-1-(hydroxymethyl)-4-phenylazetidin-2-one
• CAS: 402828-07-3
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: MIAKFLUXYCEOTD-VIFPVBQESA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  381.2±42.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 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：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-hydroxymethyl-4-phenyl-2-azetidinone 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以89%的产率得到(S)-4-phenyl-2-azetidinone
  参考文献：
  名称：

  Chemoenzymatic preparation of fluorine-substituted β-lactam enantiomers exploiting Burkholderia cepacia lipase

  摘要：

  Both enantiomers of fluorinated and non-fluorinated 4-phenyl-2-azetidinones are prepared in high enantiopurities (ee 99%) by a chemoenzymatic method, using a double resolution technique to N-hydroxymethylated beta-lactams in the presence of Burkholderia cepacia lipase as the source of enantiopurity. N-Deprotections yield the beta-lactam enantiomers from the corresponding hydroxymethylated counterparts using KMnO4 in a mixture of acetone and water. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.003
• 作为产物：
  描述：

  1-hydroxymethyl-4-phenyl-2-azetidinone 生成 (S)-1-hydroxymethyl-4-phenyl-2-azetidinone
  参考文献：
  名称：

  Convenient Syntheses of Optically Active .BETA.-Lactams by Enzymatic Resolution.

  摘要：

  通过脂肪酶催化的动力学分辨，合成了光学活性的β-内酰胺，利用N-酰氧甲基β-内酰胺（3）在有机溶剂中的对映选择性水解以及N-羟甲基β-内酰胺（2）与乙烯基醋酸酯的转酯化反应。获得了多种在3、4位或两者位置具有一些取代基的高光学纯度的β-内酰胺（2和3），所制备的光学活性的N-羟甲基β-内酰胺在不发生消旋化的情况下转化为有用的N-无取代基的形式。

  DOI：

  10.1248/cpb.41.1933

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.
• Convenient Syntheses of Optically Active .BETA.-Lactams by Enzymatic Resolution.
  作者：Hazuki NAGAI、Tatsushi SHIOZAWA、Kazuo ACHIWA、Yoshiyasu TERAO

  DOI：10.1248/cpb.41.1933

  日期：——

  Optically active β-lactams were synthesized by lipase-catalyzed kinetic resolution using the enantioselective hydrolysis of N-acyloxymethyl β-lactams (3) in an organic solvent and the transesterification of N-hydroxymethyl β-lactams (2) with vinyl acetate. A variety of highly optically pure β-lactams (2 and 3) possessing some substituents at the 3, 4, or both positions were obtained and the optically active N-hydroxymethyl β-lactams prepared were converted into useful N-unsubstituted ones without racemization.

  通过脂肪酶催化的动力学分辨，合成了光学活性的β-内酰胺，利用N-酰氧甲基β-内酰胺（3）在有机溶剂中的对映选择性水解以及N-羟甲基β-内酰胺（2）与乙烯基醋酸酯的转酯化反应。获得了多种在3、4位或两者位置具有一些取代基的高光学纯度的β-内酰胺（2和3），所制备的光学活性的N-羟甲基β-内酰胺在不发生消旋化的情况下转化为有用的N-无取代基的形式。
• Chemoenzymatic preparation of fluorine-substituted β-lactam enantiomers exploiting Burkholderia cepacia lipase
  作者：Xiang-Guo Li、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2007.10.003

  日期：2007.10

  Both enantiomers of fluorinated and non-fluorinated 4-phenyl-2-azetidinones are prepared in high enantiopurities (ee 99%) by a chemoenzymatic method, using a double resolution technique to N-hydroxymethylated beta-lactams in the presence of Burkholderia cepacia lipase as the source of enantiopurity. N-Deprotections yield the beta-lactam enantiomers from the corresponding hydroxymethylated counterparts using KMnO4 in a mixture of acetone and water. (c) 2007 Elsevier Ltd. All rights reserved.