1-(2-propenyl)-4-vinylazetidin-2-one | 102358-05-4

• 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: 1-(2-propenyl)-4-vinylazetidin-2-one
• 英文别名: 4-Ethenyl-1-prop-2-enylazetidin-2-one
• CAS: 102358-05-4
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: ZRWTUIUKQWJSCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-乙烯氮杂啶-2-酮 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 6.25h， 生成 1-(2-propenyl)-4-vinylazetidin-2-one
  参考文献：
  名称：

  Knight, John; Parsons, Philip J., Journal of the Chemical Society. Perkin transactions I, 1987, p. 1237 - 1242

  摘要：

  DOI：

文献信息

• Ring Closing Metathesis in the Synthesis of Sultones and Sultams
  作者：Peter Metz、Sandra Karsch、Dirk Freitag、Pia Schwab

  DOI：10.1055/s-2004-822408

  日期：——

  synthesized by ring closing metathesis (RCM) of sulfonates. The resulting α,β-unsaturated sultones act as dienophiles in intermolecular Diels-Alder reactions. A first cyclic sulfate formation through RCM has been discovered, and a rapid access to p-lactams fused to a sultam moiety of variable ring size was developed from inexpensive, commercially available starting materials using RCM as the key operation

  通过磺酸盐的闭环复分解（RCM）有效地合成了具有正常、中等和大环尺寸的不饱和磺内酯。所得的 α,β-不饱和磺内酯在分子间 Diels-Alder 反应中充当亲双烯体。已经发现了通过 RCM 形成的第一个环状硫酸盐，并且使用 RCM 作为关键操作，从廉价的、可商购的起始材料开发了一种快速获得稠合到可变环大小的磺胺部分的 p-内酰胺的方法。还描述了一种有效的 4-vinyl-azetidin-2-ones 生成 1-aza-bicyclo[4.2.0]oct-4-en-8-ones 的 RCM。
• New approaches to the synthesis of β-lactam antibiotics
  作者：John Knight、Philip J. Parsons、Robert Southgate

  DOI：10.1039/c39860000078

  日期：——

  New synthesis of carbapenams and carbacephams are presented using radical cyclisation techniques.

  介绍了利用自由基环化技术合成碳青霉烯类和碳青霉烯类的新方法。
• A concise synthesis of β-lactam–sulfonamide hybrids
  作者：Dirk Freitag、Pia Schwab、Peter Metz

  DOI：10.1016/j.tetlet.2004.03.055

  日期：2004.4

  Using ring closing metathesis (RCM) as the key operation, a rapid access to beta-lactams fused to a sultam moiety of variable ring size was developed from low cost, commercially available starting materials. An efficient RCM of 4-vinyl-azetidin-2ones to give I-aza-bicyclo[4.2.0]oct-4-en-8-ones is also reported. (C) 2004 Elsevier Ltd. All rights reserved.
• 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).
• KNIGHT, JOHN;PARSONS, PHILIP J., J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 6, 1237-1242
  作者：KNIGHT, JOHN、PARSONS, PHILIP J.

  DOI：——

  日期：——