trans-3-ethyl-1-(4-methoxyphenyl)-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: trans-3-ethyl-1-(4-methoxyphenyl)-4-phenylazetidin-2-one
• 英文别名: (3R,4S)-3-ethyl-1-(4-methoxyphenyl)-4-phenylazetidin-2-one
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: FSLMJCGNVLUDHZ-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-3-ethyl-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 生成 trans-3-ethyl-4-phenyl-2-azetidinone
  参考文献：
  名称：

  Sharma, Sain Datt; Anand, Rishi Dev; Kaur, Gurpreet, Journal of Chemical Research, 2005, # 4, p. 248 - 251

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(4-methoxyphenyl)-4-phenyl-3-vinylazetidin-2-one 在 镍 甲酸铵 作用下， 以 乙二醇 为溶剂， 反应 0.05h， 以85%的产率得到trans-3-ethyl-1-(4-methoxyphenyl)-4-phenylazetidin-2-one
  参考文献：
  名称：

  Microwave-Assisted Rapid and Simplified Hydrogenation^1,

  摘要：

  Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 degrees C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 degrees C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of beta-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters, Cleavage of the beta-lactam ring by hydrogenolysis of the N-C-4 bond of 4-aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.

  DOI：

  10.1021/jo981516s

文献信息

• Stereoselective one-pot synthesis of β-lactams by Lewis acid promoted condensation of silylketene thioacetals with imines
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Valentina Molteni、Olaf Schupp

  DOI：10.1016/0040-4020(95)01083-1

  日期：1996.2

  A series of silylketene thioacetals derived from 2-pyridylthioesters have been prepared and the configuration of some of them has been determined by NMR spectroscopy. In the presence of Lewis acids these compounds stereoselectively react with imines to afford β-lactams in a convenient one-pot procedure. An enantioselective β-lactam synthesis promoted by a chiral Lewis acid is also described.

  制备了一系列衍生自2-吡啶基硫酯的甲硅烷基烯酮硫缩醛，其中一些的构型已通过NMR光谱测定。在路易斯酸的存在下，这些化合物与亚胺立体选择性地反应，以方便的一锅法制得β-内酰胺。还描述了由手性路易斯酸促进的对映选择性β-内酰胺合成。
• Diastereoselective Synthesis of <i>trans</i> β-Lactams on Soluble Polymer Support
  作者：Yan-Guang Wang、Shan-Zhong Jian、Qing Yuan

  DOI：10.1055/s-2006-942358

  日期：2006.6

  Liquid-phase synthesis of trans b-lactams was accomplished through both PEG-supported imine and PEG-bound auxiliary methodologies. The trans diastereoselectivity is explained by a chair-like transition state involving the imine and the Z-enolate.

  反式β-内酯的液相合成通过PEG支持的亚胺和PEG结合的辅助方法实现。反式的二立体选择性通过涉及亚胺和Z-烯醇盐的类似椅子的过渡态来解释。
• Enantioselective one-pot synthesis of β-lactams from achiral 2-pyridylthioesters and aromatic imines
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi

  DOI：10.1016/0040-4039(94)02316-4

  日期：1995.1

  The enolates derived from 2-pyridylthioesters by reaction with BCl3 ·SMe2 and enantiomerically pure aminoalcohols react with aromatic imines in an enantioselective fashion (ee up to 78%) to afford β-lactams in a convenient one-pot procedure.

  通过与BCl 3 ·SMe 2和对映体纯的氨基醇反应而衍生自2-吡啶基硫酯的烯醇化物与芳香亚胺以对映选择性的方式反应（ee高达78％），以方便的一锅法制得β-内酰胺。
• Enantioselective Synthesis of β-Lactams Using a Chiral Auxiliary
  作者：Yan-Guang Wang、Qing Yuan、Shan-Zhong Jian

  DOI：10.1055/s-2006-939082

  日期：——

  An efficient and enantioselective synthesis of trans-β-lactams from carboximide 1 and imines 2 using a chiral auxiliary under the classical Reformatsky reaction conditions is described. An enolate-imine mechanism has been proposed for this reaction.

  本研究描述了在经典的 Reformatsky 反应条件下，使用手性助剂从羧酰亚胺 1 和亚胺 2 高效对映选择性合成反式δ-内酰胺的过程。提出了该反应的烯醇-亚胺机理。
• Synthesis of β-lactams by condensation of the tin enolates of 2-pyridylthioesters with imines. A comparison between titanium and tin enolates
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1016/s0040-4020(01)85649-0

  日期：1994.1

  SnBr4 affords the corresponding tin(IV) enolates that add to imines to give β-lactams in fair to good yields and with various degree of trans/cis stereoselectivity. Examples of highly diastereofacially selective reactions carried out on a chiral thioester and on a chiral imine are also reported. The results are compared with those obtained in the condensations promoted by TiCl4 and TiBr4.

  将三乙胺加到2-吡啶基硫代酯和SnCl 4或SnBr 4的混合物中，得到相应的锡（IV）烯醇盐，它们加到亚胺上，以公平至良好的收率和不同程度的反式/顺式立体选择性得到β-内酰胺。还报道了在手性硫酯和手性亚胺上进行的高度非对映选择性反应的实例。将结果与由TiCl 4和TiBr 4促进的缩合中获得的结果进行比较。