3-phenoxy-4-phenylazetidin-2-one

• 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: 3-phenoxy-4-phenylazetidin-2-one
• 英文别名: (3S,4R)-3-phenoxy-4-phenylazetidin-2-one
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: HOZIQJHCLIRLPF-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.17h， 以90%的产率得到3-phenoxy-4-phenylazetidin-2-one
  参考文献：
  名称：

  Stereocontrolled synthesis of N-vinyl-, N-(1'-propenyl)-, and N-unsubstituted-.beta.-lactams from 2-aza-1,3-butadienes via the Staudinger reaction

  摘要：

  2-Aza-1,3-butadienes 2 and 5 were synthesized in good yields and on a large scale. Reaction of 2 and 5 with acid chlorides in the presence of triethylamine (Staudinger reaction) resulted in the high-yielding formation of N-vinyl- and N-(1'-propenyl)-beta-lactams. Excellent cis-stereoselectivity was observed in the reaction of 2-aza-1,3-butadienes 2 and 5 with Bose-Evans ketenes and Sheehan ketenes, whereas reaction with a Moore ketene gave, as expected, a trans beta-lactam. N-Formyl, N-vinyl, and N-(1'-propenyl) groups at the beta-lactam nitrogen could be cleaved oxidatively in one step and in good yields by treatment with potassium permanganate. It was also found that the N-vinyl group can be removed successfully under hydrolytic, conditions to yield N-unsubstituted-beta-lactams.

  DOI：

  10.1021/jo00073a042

文献信息

• Synthesis of N1-unsubstituted β-lactams via a facile deprotection of N1-[(α-thiophenyl)benzyl] group
  作者：K. Karupaiyan、V. Srirajan、A.R.A.S. Deshmukh、B.M. Bhawal

  DOI：10.1016/s0040-4020(98)00151-3

  日期：1998.4

  A diastereoselective synthesis of (±) cis-β-lactams (5 & 6) via cycloaddition reactions of N1-(α-thiophenyl)benzyl imines (3) with acid chlorides (4) in the presence of triethylamine is described. The deprotection of N1-(α-thiophenyl)benzyl group has been achieved by oxidation using potassium persulfate to give N-unsubstituted β-lactams (7) in good yields.

  描述了在三乙胺存在下，通过N1-（α-硫代苯基）苄基亚胺（3）与酰氯（4）的环加成反应，非对映选择性地合成（±）顺式-β-内酰胺（5和6）。N1-（α-硫代苯基）苄基的脱保护已经通过使用过硫酸钾的氧化来实现，从而以良好的收率得到N-未取代的β-内酰胺（7）。
• N-vinyl and N-unsubstituted β-lactams from 1-substituted 2-aza-1, 3-butadienes
  作者：Gunda I. Georg、Ping He、Joydeep Kant、Jeffrey Mudd

  DOI：10.1016/0040-4039(90)87005-k

  日期：1990.1
• Arrieta, Ana; Lecea, Begona; Palomo, Claudio, Journal of the Chemical Society. Perkin transactions I, 1987, p. 845 - 850
  作者：Arrieta, Ana、Lecea, Begona、Palomo, Claudio

  DOI：——

  日期：——
• 2-aza-1,3-dienes as novel precursors for the synthesis of -unsubstituted β-lactams. A three step synthesis of 4-acetoxy-3-phenoxy-2-azeridinone
  作者：Gunda I Georg、Joydeep Kant、Ping He、Ana Maria Ly、Lynn Lampe

  DOI：10.1016/s0040-4039(00)87894-6

  日期：1988.1
• Synthesis of N1-unsubstituted β-lactams: Introducing N1-(1′-thiophenyl)benzyl as an N-protecting group
  作者：K. Karupaiyan、V. Srirajan、A.R.A.S. Deshmukh、B.M. Bhawal

  DOI：10.1016/s0040-4039(97)00879-4

  日期：1997.6

  A diastereoselective synthesis of (+/-) cis-beta-lactams (5 & 6) via cycloaddition reaction of N-1-(alpha-thiophenyl)benzyl imines (3) with acid chlorides (4) in the presence of triethyl amine is described. Deprotection of N-1-(alpha-thiophenyl)benzyl group was achieved in good yields by oxidation using potassium persulfate. (C) 1997 Elsevier Science Ltd.