(3R,4R)-3-fluoro-4-phenylazetidin-2-one | 951259-44-2

• 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: (3R,4R)-3-fluoro-4-phenylazetidin-2-one
• CAS: 951259-44-2
• 化学式: C₉H₈FNO
• 分子量: 165.167
• InChiKey: YIWIHTWNUFNIPO-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-fluoro-4-phenylazetidin-2-one 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.92h， 以80%的产率得到tert-butyl (3R,4R)-3-fluoro-2-oxo-4-phenylazetidine-1-carboxylate
  参考文献：
  名称：

  Burkholderia cepacia lipase and activated β-lactams in β-dipeptide and β-amino amide synthesis

  摘要：

  The work describes fluorine-activated and N-Boc-activated beta-lactams as acyl donors to N-nucleophiles in the presence of Burkholderia cepacia lipase (lipase PS-D). Fluorine activation at the beta-lactam ring causes the ring to open in high enantioselectivity and allows the preparation of beta-dipeptides and beta-amino amides. in the case of N-Boc-activation, the chemical ring opening is significant. beta-Dipeptide formation can then be considerably enhanced by the presence of lipase PS-D and/or by temperature. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.017
• 作为产物：
  描述：

  (3R,4R)-3-fluoro-1-(hydroxymethyl)-4-phenylazetidin-2-one 在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 反应 125.0h， 以84%的产率得到(3R,4R)-3-fluoro-4-phenylazetidin-2-one
  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

文献信息

• Enantioselective acylation of alcohols with fluorinated β-phenyl-β-lactams in the presence of Burkholderia cepacia lipase
  作者：Xiang-Guo Li、Maria Lähitie、Mari Päiviö、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2007.06.033

  日期：2007.7

  the acylation of alcohols with 3,3-difluoro-4-phenylazetidin-2-one rac-1, trans-3-fluoro-4-phenylazetidin-2-one rac-2 and 4-phenylazetidin-2-one rac-3 in the presence of immobilized lipase PS from Burkholderia cepacia in dry tert-butyl methyl ether (TBME). Fluorine activation in the compounds studied was essential in order to split the β-lactam ring with lipase PS. The highly enantioselective ring

  本文着重研究醇与3,3-二氟-4-苯基氮杂环丁烷-2-one rac - 1，反式-3-氟-4-苯基氮杂环丁烷-2-one rac - 2和4-苯基氮杂环丁烷2的酰化作用。-酮的外消旋- 3中存在固定的脂肪酶PS从洋葱伯克霍尔德氏菌的无水叔丁基甲基醚（TBME）。为了用脂肪酶PS裂解β-内酰胺环，所研究化合物中的氟活化是必不可少的。rac - 1和rac - 2的高对映选择性开环用甲醇（还研究了1-丁醇）可以制备（R /（3 R，4 R））-β-内酰胺类未反应的对映体和（S /（2 S，3 S））-β-氨基酯为对映体，ee≥99％。在相同条件下，rac - 3完全不起作用。还讨论了酶制剂中水引起竞争性水解的可能性。
• Burkholderia cepacia lipase and activated β-lactams in β-dipeptide and β-amino amide synthesis
  作者：Xiang-Guo Li、Maria Lähitie、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2008.07.017

  日期：2008.8

  The work describes fluorine-activated and N-Boc-activated beta-lactams as acyl donors to N-nucleophiles in the presence of Burkholderia cepacia lipase (lipase PS-D). Fluorine activation at the beta-lactam ring causes the ring to open in high enantioselectivity and allows the preparation of beta-dipeptides and beta-amino amides. in the case of N-Boc-activation, the chemical ring opening is significant. beta-Dipeptide formation can then be considerably enhanced by the presence of lipase PS-D and/or by temperature. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.