trans-3-ethyl-4-phenyl-2-azetidinone | 90696-14-3

• 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: trans-3-ethyl-4-phenyl-2-azetidinone
• 英文别名: 3-ethyl-4-phenylazetidin-2-one；(3S,4R)-3-ethyl-4-phenylazetidin-2-one
• CAS: 90696-14-3
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: YAUCTLNBMDWRBQ-UWVGGRQHSA-N

物化性质

• 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

• 作为产物：
  描述：

  在 potassium tert-butylate 、 mercury dichloride 、 锌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 生成 trans-3-ethyl-4-phenyl-2-azetidinone
  参考文献：
  名称：

  .beta.-Tosylethylamine: A Useful Reagent for Preparation of N-Protected Amides, Carbamates, and Related Compounds. Application to Synthesis of .beta.-Lactams

  摘要：

  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.

  DOI：

  10.1021/jo00099a006

文献信息

• Silicon-assisted synthesis of β-lactams
  作者：Ernest W. Colvin、Daniel McGarry、Mark J. Nugent

  DOI：10.1016/s0040-4020(01)86663-1

  日期：1988.1

  Reaction of -silyl imines with silyi ketene acetals in the presence of ZnI2 and t-butyl alcohol, followed by treatment of the intermediate -silyl β-aminoesters with MeMgBr, produces -silyl-azetidin-2-ones in good yield; use of trimethylsilyl triflate as Lewis acid catalyst can be advantageous in some cases. The preparation of the -t-butyldimethylsilyl imine of ethyl glyoxylate in this context is detailed

  -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。
• 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。
• Optically Active Aminoalcohol Promoted Addition of 2-Pyridylthioester Boron Enolates to Imines: Enantioselective One-pot Synthesis of β-Lactams
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Valentina Molteni、Laura Raimondi

  DOI：10.1016/0040-4020(95)00503-z

  日期：1995.8

  The enolates derived from 2-pyridylthioesters by treatment with BCl3 . Me(2)S and enantiomerically pure aminoalcohols react with aromatic and heteroaromatic imines to afford beta-lactams in a convenient one-pot procedure and in up to 78% e.e. The aminoalcohol can be employed both as the metal ligand and as the base to generate the enolate. Among several aminoalcohols tested, N-methylephedrine turned our to be the more efficient in terms of stereoselectivity.
• Sharma, Sain Datt; Anand, Rishi Dev; Kaur, Gurpreet, Journal of Chemical Research, 2005, # 4, p. 248 - 251
  作者：Sharma, Sain Datt、Anand, Rishi Dev、Kaur, Gurpreet

  DOI：——

  日期：——
• 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