1-(4-Methoxyphenyl)-3-methyl-4-<(E)-2-phenylethenyl>-azetidin-2-one | 135616-56-7

• 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-(4-Methoxyphenyl)-3-methyl-4-<(E)-2-phenylethenyl>-azetidin-2-one
• 英文别名: syn-1-(p-methoxyphenyl)-3-methyl-4-styrylazetidin-2-one；(3S,4R)-1-(4-methoxyphenyl)-3-methyl-4-[(E)-2-phenylethenyl]azetidin-2-one
• CAS: 135616-56-7；135683-01-1
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: APFGKJBYELBOCL-LEDHSJFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3S,4S)-1-(4-methoxyphenyl)-3-methyl-4-[(E)-2-phenylethenyl]-3-phenylsulfanylazetidin-2-one 、 (3S,4R)-1-(4-methoxyphenyl)-3-methyl-4-[(E)-2-phenylethenyl]-3-phenylsulfanylazetidin-2-one 、 二丁基锡烷 生成 1-(4-Methoxyphenyl)-3-methyl-4-<(E)-2-phenylethenyl>-azetidin-2-one
  参考文献：
  名称：

  PALOMO, CLAUDIO;COSSIO, FERNANDO P.;ODIZOLA, JOSE M.;OIARBIDE, MIKEL;ONTO+, J. ORG. CHEM., 56,(1991) N4, C. 4418-4428

  摘要：

  DOI：

文献信息

• Diastereoselective Synthesis of <i>syn</i>-β-Lactams Using Rh-Catalyzed Reductive Mannich-Type Reaction of α,β-Unsaturated Esters
  作者：Motoyuki Isoda、Kazuyuki Sato、Masato Funakoshi、Keiko Omura、Atsushi Tarui、Masaaki Omote、Akira Ando

  DOI：10.1021/acs.joc.5b01233

  日期：2015.8.21

  The combination of Et2Zn and RhCl(PPh3)3 led to the facile generation of a rhodium–hydride complex (Rh–H) that catalyzed the 1,4-reduction of α,β-unsaturated esters. The resulting rhodium enolate performed as a Reformatsky-type reagent and reacted with various imines to give syn-β-lactams in good to excellent yields with high diastereoselectivity.

  Et 2 Zn和RhCl（PPh 3）3的组合导致容易生成铑-氢化物络合物（Rh-H），该络合物催化α，β-不饱和酯的1,4-还原。所得的烯醇铑作为Reformatsky型试剂起作用，并与各种亚胺反应，以良好的非对映异构体收率以优异的产率得到合成的-β-内酰胺。
• 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。
• The synthesis of β-lactams via a one-pot Reformatsky reaction of imines promoted by Zn/Cp2TiCl2 (cat.)
  作者：Lei Chen、Gang Zhao、Yu Ding

  DOI：10.1016/s0040-4039(03)00187-4

  日期：2003.3

  In the presence of Zn/Cp2TiCl2 (cat.) alpha-bromoacetates, gamma-bromocrotonates or alpha-bromomethylacrylates react with imines in one-pot to form beta-lactams, 3-vinyl-beta-lactams or alpha-methylene-gamma-lactams, respectively, at room temperature without the need for pretreatment of the solvent and Zn. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Preparation of 3-alkyl .beta.-lactams via the ketene imine cycloaddition reaction using .alpha.-(phenylthio)alkanoyl halides as starting materials: application to the synthesis of (.+-.)-carbapenem building blocks and related compounds
  作者：Claudio Palomo、Fernando P. Cossio、Jose M. Odiozola、Mikel Oiarbide、Jesus M. Ontoria

  DOI：10.1021/jo00014a017

  日期：1991.7

  Preparation of appropriately substituted 3-alkyl beta-lactams via the ketene (or equivalent)-imine cycloaddition reaction is described. The dehydrochlorination reaction of alpha-(phenylthio)alkanoyl chlorides with triethylamine in the presence of imines derived from cinnamaldehydes and p-anisidine produced a high-yield formation of alpha-phenylthio beta-lactams, which upon desulfuration furnished a variety of 3-alkyl beta-lactams in a highly stereoselective fashion. In contrast, reaction between alpha-haloalkanoyl chlorides and cinnamylideneamines in the presence of triethylamine furnished the corresponding [4 + 2] cycloadducts as main products. Preparation of highly functionalized alpha-alkylidene beta-lactams through thermal decomposition of the corresponding beta-lactam sulfoxides or by cycloaddition of alpha,beta-unsaturated acid chlorides to imino esters in the presence of triethylamine is also described. Addition of Flemming's silylcuprate reagent to alpha-alkylidene beta-lactams furnished the corresponding 3-(1'-(dimethylphenylsilyl(ethyl) beta-lactams as (+/-)-thienamycin intermediates.
• Mild and convenient one-pot synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines.
  作者：Mauro Cinquini、Franco Cozzi、Pier Giorgio Cozzi、Emanuela Consolandi

  DOI：10.1016/s0040-4020(01)96198-8

  日期：1991.10

  Treatment of 2-pyridylthioesters with triethylamine in the presence of titanium tetrachloride affords titanium enolates that add to imines to give beta-lactams in fair to excellent yields with moderate to good stereoselectivity.