1-(4-methoxyphenyl)-3-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-4-phenylazetidin-2-one | 141781-30-8

• 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-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-4-phenylazetidin-2-one
• CAS: 141781-30-8
• 化学式: C₂₄H₃₃NO₃Si
• 分子量: 411.616
• InChiKey: MSDZBJDKEPBZOR-ZPMCFJSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 sodium hydroxide 、 四氯化钛 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.08h， 生成 1-(4-methoxyphenyl)-3-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-4-phenylazetidin-2-one
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines

  摘要：

  A mild and versatile one-pot synthesis of beta-lactams has been performed by condensation of the easily generated titantium enolates of 2-pyridyl thioesters with imines employing chiral reaction partners. Both imines obtained from enantiomerically pure alkoxy aldehydes and the enolate derived from 3-hydroxybutyrate showed high diastereofacial preferences, efficiently transferring the stereochemical information to the stereocenters of the azetidinone ring. Advanced precursors of (+)-PS-5, (+)-PS-6, thienamycin, and 1-beta-methylthienamycin were prepared to illustrate the potential of this method. A H-1-NMR study of the enolization process and a tentative rationalization of the stereochemical results are presented.

  DOI：

  10.1021/jo00041a019

文献信息

• 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。
• Soluble polymer-supported synthesis of imines and β-lactams
  作者：Valentina Molteni、Rita Annunziata、Mauro Cinquini、Franco Cozzi、Maurizio Benaglia

  DOI：10.1016/s0040-4039(97)10770-5

  日期：1998.3

  The first synthesis of β-lactams bound to a soluble/insoluble polyethylene glycol monomethylether polymeric matrix has been realized by standard reactions carried out on immobilized imines. β-Lactams removal from the polymer has been accomplished under acidic and basic conditions.

  通过在固定化的亚胺上进行的标准反应，已经实现了与可溶/不可溶的聚乙二醇单甲醚聚合物基体结合的β-内酰胺的首次合成。从聚合物中去除β-内酰胺是在酸性和碱性条件下完成的。
• Synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines. Influence of the imine structure on the trans/cis stereoselectivity
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Francesco Ponzini、Laura Raimondi

  DOI：10.1016/s0040-4020(01)87005-8

  日期：1994.2

  The condensation of the titanium enolates of C-2 alkyl substituted 2-pyridylthioesters with imines affords beta-lactams in trans/cis ratios that largely depend on the structure of the C-imine residue. Bulky and non-chelating heteroatom-containing groups lead to the formation of trans p-lactams, while sterically non-requiring or chelating groups favour the formation of the cia-products. On the basis of NMR evidences a rationale is proposed to account for the observed stereoselectivity.