| 183578-32-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 183578-32-7
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: HJZLJVTZUJOOAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  13.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  61.55
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到2-(4,7-Dihydro-1,3-dioxepin-2-yl)acetamide
  参考文献：
  名称：

  Alkene metathesis in the synthesis of novel β-lactams

  摘要：

  Both monocyclic and bicyclic beta-lactams systems are prepared via alkene metathesis reactions using Mo(=CHCMe(2)Ph)(=NC6H3Pr2i-2,6)[OCMe(CF3)(2)](2) or Ru(=HPh)Cl-2(PCy(3))(2).

  DOI：

  10.1039/cc9960002231
• 作为产物：
  描述：

  4-(2-propenyl-1-oxy)azetidin-2-one 在 溴甲苯 、 sodium hydride 作用下， 以83%的产率得到N-benzyl-4-allyloxy-azetidin-2-one
  参考文献：
  名称：

  Alkene metathesis in the synthesis of novel β-lactams

  摘要：

  Both monocyclic and bicyclic beta-lactams systems are prepared via alkene metathesis reactions using Mo(=CHCMe(2)Ph)(=NC6H3Pr2i-2,6)[OCMe(CF3)(2)](2) or Ru(=HPh)Cl-2(PCy(3))(2).

  DOI：

  10.1039/cc9960002231

文献信息

• Rapid Entry into Mono-, Bi-, and Tricyclic β-Lactam Arrays via Alkene Metathesis
  作者：Anthony G. M. Barrett、Simon P. D. Baugh、D. Christopher Braddock、Kevin Flack、Vernon C. Gibson、Matthew R. Giles、Edward L. Marshall、Panayiotis A. Procopiou、Andrew J. P. White、David J. Williams

  DOI：10.1021/jo981150j

  日期：1998.10.1

  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).