3-ethyl-4-phenylazetidin-2-one | 90696-10-9

• 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-ethyl-4-phenylazetidin-2-one
• 英文别名: (3R,4R)-3-ethyl-4-phenylazetidin-2-one
• CAS: 90696-10-9
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: YAUCTLNBMDWRBQ-ZJUUUORDSA-N

物化性质

• 熔点：
  122-123 °C
• 沸点：
  356.8±31.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-ethyl-4-phenylazetidin-2-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 ((1S,2S)-4-Diazo-2-ethyl-3-oxo-1-phenyl-butyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  三甲基甲硅烷基重氮甲烷将β-内酰胺的立体定向扩环为γ-内酰胺

  摘要：

  用三甲基甲硅烷基重氮甲烷阴离子将N-羧基化的β-内酰胺开环，然后进行光解Wolff重排，以立体有择的方式提供了γ-内酰胺。

  DOI：

  10.1016/s0040-4039(98)01640-2
• 作为产物：
  描述：

  苯甲醛 在 正丁基锂 、 三甲基氯硅烷 作用下， 反应 1.45h， 生成 3-ethyl-4-phenylazetidin-2-one
  参考文献：
  名称：

  硅辅助合成β-内酰胺

  摘要：

  -甲硅烷基亚胺与甲硅烷基乙烯酮缩醛在ZnI 2和叔丁醇的存在下反应，然后用MeMgBr处理中间体-甲硅烷基β-氨基酯，以高收率产生-甲硅烷基-氮杂环丁烷-2-酮。在某些情况下，使用三氟甲磺酸三甲基甲硅烷基酯作为路易斯酸催化剂可能是有利的。在此上下文中，详细描述了乙醛酸乙酯的叔丁基二甲基甲硅烷基亚胺的制备。

  DOI：

  10.1016/s0040-4020(01)86663-1

文献信息

• Reaction of silyl ketene acetals with N-trimethylsilyl imines: a route to N-unsubstituted azetidin-2-ones
  作者：Ernest W. Colvin、Daniel G. McGarry

  DOI：10.1039/c39850000539

  日期：——

  Reaction of N-trimethylsilyl imines with silyl ketene acetals in the presence of ZnI2 and t-butyl alcohol, followed by treatment in situ of the intermediate N-silyl β-aminoesters with MeMgBr, leads to N-unsubstituted azetidin-2-ones in good yield.

  在ZnI 2和叔丁醇存在下，N-三甲基甲硅烷基亚胺与甲硅烷基烯酮缩醛反应，然后用MeMgBr原位处理中间的N-甲硅烷基β-氨基酯，生成N-未取代的氮杂环丁烷-2-酮良品率高。
• N-Trimethylsilylimines: applications to the syntheses of .beta.-lactams
  作者：Deok Chan Ha、David J. Hart、Teng Kuei Yang

  DOI：10.1021/ja00329a029

  日期：1984.8
• .beta.-Tosylethylamine: A Useful Reagent for Preparation of N-Protected Amides, Carbamates, and Related Compounds. Application to Synthesis of .beta.-Lactams
  作者：Darren DiPietro、Robert M. Borzilleri、Steven M. Weinreb

  DOI：10.1021/jo00099a006

  日期：1994.10

  Readily prepared beta-tosylethylamine (3) can be used to synthesize N-tosylethyl (TSE)-protected amido compounds and beta-lactams, which can be deprotected under mild conditions with potassium tert-butoxide.
• Asymmetric synthesis of .beta.-lactams and the carbapenem antibiotic (+)-PS-5
  作者：David J. Hart、Chih Shone. Lee、William H. Pirkle、Myung Ho. Hyon、Athanasios. Tsipouras

  DOI：10.1021/ja00279a072

  日期：1986.9
• Soluble-Polymer-Supported Synthesis ofβ-Lactams on a Modified Poly(ethylene glycol)
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi

  DOI：10.1002/(sici)1521-3765(20000103)6:1<133::aid-chem133>3.0.co;2-h

  日期：2000.1.3

  A modified poly(ethylene glycol) (PEG) has been developed for the soluble-polymer-supported synthesis of beta-lactams. The monomethylether of PEG (MeOPEG) with an average M-W of 5000 was used as the support, a 4-(3-propyl)phenyl residue as the spacer, and a 4-oxyphenylamino group as the moiety with the reactive functionality. From this modified PEG representative aromatic, heteroaromatic, unsaturated, and aliphatic imines were obtained in high yields by different procedures. The polymer-supported imines were then employed to prepare several beta-lactams by enolate/imine condensation and ketene/imine cycloaddition. Examples of the control of the absolute stereochemistry during the azetidinone ring formation are also reported. The reactions carried out on the polymer-bound imines showed a remarkable similarity to those performed on nonimmobilized imines, both in terms of yields and stereoselectivities. Removal of the beta-lactams from the polymer has also been accomplished to directly deliver the N-unsubstituted azetidinones.