(3S,4R)-4-(4-methoxyphenyl)-3-phenylmethoxyazetidin-2-one | 145654-57-5

• 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: (3S,4R)-4-(4-methoxyphenyl)-3-phenylmethoxyazetidin-2-one
• CAS: 145654-57-5
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: ZMANMYXLXWUXHZ-CVEARBPZSA-N

物化性质

• 沸点：
  497.2±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-(4-methoxyphenyl)-3-phenylmethoxyazetidin-2-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 7.0h， 生成 (2R,3R)-3-Benzyloxy-2-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  三甲基甲硅烷基重氮甲烷将β-内酰胺的立体定向扩环为γ-内酰胺

  摘要：

  用三甲基甲硅烷基重氮甲烷阴离子将N-羧基化的β-内酰胺开环，然后进行光解Wolff重排，以立体有择的方式提供了γ-内酰胺。

  DOI：

  10.1016/s0040-4039(98)01640-2
• 作为产物：
  描述：

  cis-4-p-Anisyl-1-<(4'-methoxybenzylidene)amino>-3-benzyloxy-2-azetidinone 在 臭氧 、 溶剂黄146 、 锌 作用下， 生成 (3S,4R)-4-(4-methoxyphenyl)-3-phenylmethoxyazetidin-2-one
  参考文献：
  名称：

  2,3-Diaza-1,3-dienes (Azines) as Substrates for the Staudinger Reaction. Synthesis and Reactivity of N-Imino-.beta.-lactams

  摘要：

  The reaction of aromatic and aliphatic azines with different ketene precursors, such as the acid chloride/Et(3)N system, alkoxychromium(0) carbenes, and free diphenyl ketene, gives N-imino-beta-lactams in good to excellent yields, with good levels of cis,trans-selectivity. A wide variety of symmetrically-substituted azines derived from aldehydes and ketones are compatible with the Staudinger reaction. Chiral N-imino-beta-lactams derived from symmetrically or unsymmetrically (mixed) chiral azines are also obtained in good yields as essentially single enantiomers (de > 95%). Different reaction intermediates, including hemiaminals, oxadiazols, and hydrazides have been isolated. Free diphenyl ketene forms Diels-Alder adducts and N-acylazadienes in addition to the previously reported N-imino-beta-lactams, The usual reactivity of the beta-lactam ring is modified in N-imino-beta-lactams by the presence of the imino group. Thus, beta-hydrazonoesters, N-alkylamino-beta-lactams, and NH-beta-lactams can be efficiently obtained by base-catalyzed 2-azetidinone ring opening, catalytic hydrogenation, and ozonolysis, respectively.

  DOI：

  10.1021/jo00105a014

文献信息

• Highly <i>syn</i>-Diastereoselective Synthesis of <i>NH</i>-3-Benzyloxy-4-aryl-azetidin-2-ones via a Two-Step Staudinger Reaction
  作者：Sergio Bacchi、Alessandro Bongini、Mauro Panunzio、Marzia Villa

  DOI：10.1055/s-1998-1793

  日期：1998.8

  New conditions for the Staudinger reaction provide NH-3-benzyloxy-4-aryl-β-lactams in good yields with complete cis-diastereoselectivity.

  斯陶丁格反应的新条件提供了NH-3-苄氧基-4-芳基-β-内酰胺，具有良好的产率和完全的顺式立体选择性。
• A novel fragmentation of the .beta.-lactam ring: stereoselective entry to vinyl ethers by reaction of N-(arylidene(or alkylidene)amino)-2-azetidinones with ozone
  作者：Benito Alcaide、Miguel Miranda、Javier Perez-Castells、Miguel A. Sierra

  DOI：10.1021/jo00054a003

  日期：1993.1

  The title compounds undergo a novel 2-azetidinone ring fragmentation by reaction with ozone followed by NaBH4 workup to stereoselectively yield vinyl ethers via intermediate N-nitroso-beta-lactams.