(2S,3R)-3-Ethyl-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid tert-butyl ester | 117901-09-4

• 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: (2S,3R)-3-Ethyl-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,3R)-3-ethyl-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate
• CAS: 117901-09-4
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: RBSOVMOEEFVDCQ-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (2S,3R)-1-(4-Methoxy-phenyl)-4-oxo-3-vinyl-azetidine-2-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到(2S,3R)-3-Ethyl-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A new enantio and diastereoselective synthesis of 2-azetidinones as useful intermediates of β-lactan antibiotics

  摘要：

  DOI：

  10.1016/s0040-4039(00)80218-x

文献信息

• A new synthesis of .beta.-lactams through stereoselective oxidative coupling of the dianions of acyclic amides
  作者：Takeo Kawabata、Kenzo Sumi、Tamejiro Hiyama

  DOI：10.1021/ja00199a055

  日期：1989.8

  La synthese du noyau β-lactame se fait via la copulation oxydante d'enolate d'amide utilisant le N-iodo succinimide en tant qu'oxydant

  La 合成 du noyau β-内酰胺本身 fait via la copulation oxydante d'enolate d'amide utilisant le N-iodo succinimide en tant qu'oxydant
• Stereoselective synthesis of .beta.-lactams by oxidative coupling of dianions of acyclic tertiary amides
  作者：Takeo Kawabata、Tatsuya Minami、Tamejiro Hiyama

  DOI：10.1021/jo00032a047

  日期：1992.3

  Tertiary amides RCH2CON(R')CH2Z, where Z is an electron-withdrawing group, were converted into dianions by treatment with 2 equiv of n-butyllithium or tert-butyllithium, and the dianions were oxidized with N-iodosuccinimide (NIS) or a Cu(II) carboxylate to form beta-lactams stereoselectively. The stereochemistry of beta-lactam formation depends on the oxidant; NIS is cis-selective, whereas Cu(II) is nonselective or slightly trans-selective. A high degree of asymmetric induction in the formation of beta-lactams was achieved by using (R)-1-phenylethylamine as a chiral auxiliary. This asymmetric ring closure was applied to the preparation of cis-beta-lactam 31, an intermediate for the synthesis of the monobactam antibiotic carumonam.
• Diastereoselective Conjugate Reduction and Enolate Trapping with Glyoxylate Imines. A Concise Approach to β-Lactams that Involves a Ternary Combination of Components
  作者：Claudio Palomo、Jesús M Aizpurua、Jose Javier Gracenea

  DOI：10.1021/jo981574d

  日期：1999.3.1
• BONINI, CARLO;DI, FABIO ROMANO, TETRAHEDRON LETT., 29,(1988) N 7, 815-818
  作者：BONINI, CARLO、DI, FABIO ROMANO

  DOI：——

  日期：——