ethyl 2-[2-oxo-4-(2-propenyl)azetidinyl]-2-(2-propenyl-1-oxy)acetate | 216856-25-6

• 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: ethyl 2-[2-oxo-4-(2-propenyl)azetidinyl]-2-(2-propenyl-1-oxy)acetate
• 英文别名: Ethyl 2-(2-oxo-4-prop-2-enylazetidin-1-yl)-2-prop-2-enoxyacetate
• CAS: 216856-25-6
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: YQRUJOAKGIAXAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-[2-oxo-4-(2-propenyl)azetidinyl]-2-(2-propenyl-1-oxy)acetate 在 (CF3)2MeCO>2Mo(=CHCMe2Ph)(=NC6H3-2,6-iso-Pr2) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (Z)-(2R,8R)-10-Oxo-3-oxa-1-aza-bicyclo[6.2.0]dec-5-ene-2-carboxylic acid ethyl ester 、 (Z)-(2R,8S)-10-Oxo-3-oxa-1-aza-bicyclo[6.2.0]dec-5-ene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Rapid Entry into Mono-, Bi-, and Tricyclic β-Lactam Arrays via Alkene Metathesis

  摘要：

  4-Acetoxy-2-azetidinone and (3R,4R)-4-acetoxy-3-[(1R)-1-(tert-butyldimethylsilyl)-oxyethyl]-2-azetidinone were converted into 4-alkenyloxy-, 4-(N-allyltoluene-4-sulfonamido)-, 4-(allylthio)-, and 4-alkenyl-2-azetidinone systems. In addition, 4-acetoxy-2-azetidinone and (3R,4R)-4-acetoxy-3-[(1R)-1-(tert-butyldimethylsilyl)-oxyethyl]-2-azetidinone were converted into beta-lactam dienes via sequential C-4 substitution using unsaturated alcohols, allyl mercaptan, N-allyltoluene-4-sulfonamide, and allyl(chloro)dimethylsilane followed by N-allylation. Crossed metathesis of beta-lactam alkenes with styrene partners and ring closing metathesis of beta-lactam dienes using the Schrock [(CF3)(2)MeCO](2)Mo(=CHCMe2Ph)(=NC6H3-2,6-iso-Pr-2) (1) or Grubbs Cl-2(Cy3P)(2)Ru=CHPh (2) carbenes gave diverse monocyclic and bicyclic beta-lactam systems including derivatives of 1-azabicyclo[4.2.0]octan-8-one, 1-azabicyclo[5.2.0]nonan-9-one and its 6-thia, 6-aza, and 6-oxa analogues, 7-oxa-1-azabicyclo[6.2.0]octan-10-one, 8-oxa-1-azabicyclo[7.2.0]octan-11-one, and 9-oxa-1-azabicyclo[8.2.0]octan-12-one. Ring-closing enyne metathesis and tandem ring-closing enyne and diene metathetic reactions were used to produce bicyclic beta-lactam conjugated dienes as exemplified by the conversion of (3S,4R)-(-)-3-[(1R)-(tert-butyldimethylsilyl)oxyethyl]-1-(5-oxa-oct-7-en-2-yn-1-yl)-4-(2-propenyl)-azetidin-2-one (83) into (6R,7S)-(+)-7-[(1R)-(tert-butyldimethylsilyl)oxyethyl]-3-[(2,5-dihydro)-3-furanyl]-1-azabicyclo[4.2.0]oct-3-en-8-one (98).

  DOI：

  10.1021/jo981150j
• 作为产物：
  描述：

  4-allylazetidin-2-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 20.0h， 生成 ethyl 2-[2-oxo-4-(2-propenyl)azetidinyl]-2-(2-propenyl-1-oxy)acetate
  参考文献：
  名称：

  Rapid Entry into Mono-, Bi-, and Tricyclic β-Lactam Arrays via Alkene Metathesis

  摘要：

  4-Acetoxy-2-azetidinone and (3R,4R)-4-acetoxy-3-[(1R)-1-(tert-butyldimethylsilyl)-oxyethyl]-2-azetidinone were converted into 4-alkenyloxy-, 4-(N-allyltoluene-4-sulfonamido)-, 4-(allylthio)-, and 4-alkenyl-2-azetidinone systems. In addition, 4-acetoxy-2-azetidinone and (3R,4R)-4-acetoxy-3-[(1R)-1-(tert-butyldimethylsilyl)-oxyethyl]-2-azetidinone were converted into beta-lactam dienes via sequential C-4 substitution using unsaturated alcohols, allyl mercaptan, N-allyltoluene-4-sulfonamide, and allyl(chloro)dimethylsilane followed by N-allylation. Crossed metathesis of beta-lactam alkenes with styrene partners and ring closing metathesis of beta-lactam dienes using the Schrock [(CF3)(2)MeCO](2)Mo(=CHCMe2Ph)(=NC6H3-2,6-iso-Pr-2) (1) or Grubbs Cl-2(Cy3P)(2)Ru=CHPh (2) carbenes gave diverse monocyclic and bicyclic beta-lactam systems including derivatives of 1-azabicyclo[4.2.0]octan-8-one, 1-azabicyclo[5.2.0]nonan-9-one and its 6-thia, 6-aza, and 6-oxa analogues, 7-oxa-1-azabicyclo[6.2.0]octan-10-one, 8-oxa-1-azabicyclo[7.2.0]octan-11-one, and 9-oxa-1-azabicyclo[8.2.0]octan-12-one. Ring-closing enyne metathesis and tandem ring-closing enyne and diene metathetic reactions were used to produce bicyclic beta-lactam conjugated dienes as exemplified by the conversion of (3S,4R)-(-)-3-[(1R)-(tert-butyldimethylsilyl)oxyethyl]-1-(5-oxa-oct-7-en-2-yn-1-yl)-4-(2-propenyl)-azetidin-2-one (83) into (6R,7S)-(+)-7-[(1R)-(tert-butyldimethylsilyl)oxyethyl]-3-[(2,5-dihydro)-3-furanyl]-1-azabicyclo[4.2.0]oct-3-en-8-one (98).

  DOI：

  10.1021/jo981150j