cis-3-isopropyl-1-(p-methoxyphenyl)-4-phenyl-2-azetidinone | 90696-12-1

• 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: cis-3-isopropyl-1-(p-methoxyphenyl)-4-phenyl-2-azetidinone
• 英文别名: (3S,4S)-1-(4-methoxyphenyl)-4-phenyl-3-propan-2-ylazetidin-2-one
• CAS: 90696-12-1
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: GTBDTBOMJABTLL-ZWKOTPCHSA-N

物化性质

• 沸点：
  503.4±50.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  异戊酸乙酯 、 N-亚苄基-4-甲氧基苯胺 在 正丁基锂 、 二异丙胺 作用下， 生成 cis-3-isopropyl-1-(p-methoxyphenyl)-4-phenyl-2-azetidinone 、 trans-3-isopropyl-1-(p-methoxyphenyl)-4-phenyl-2-azetidinone
  参考文献：
  名称：

  N-Trimethylsilylimines: applications to the syntheses of .beta.-lactams

  摘要：

  DOI：

  10.1021/ja00329a029

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。
• 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.
• 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.