N-<<(S)-2-oxo-4-isopropyloxazoline-3-carbonyl>methyl>-N-(4-methoxyphenyl)butanamide | 138924-40-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-<<(S)-2-oxo-4-isopropyloxazoline-3-carbonyl>methyl>-N-(4-methoxyphenyl)butanamide
• 英文别名: N-[((S)-2-oxo-4-isopropyloxazoline-3-carbonyl)methyl]-N-(4-methoxyphenyl)butanamide；N-(4-methoxyphenyl)-N-[2-oxo-2-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]ethyl]butanamide
• CAS: 138924-40-0
• 化学式: C₁₉H₂₆N₂O₅
• 分子量: 362.426
• InChiKey: AATWVMZQGNLCOC-MRXNPFEDSA-N

物化性质

• 沸点：
  539.1±35.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-<<(S)-2-oxo-4-isopropyloxazoline-3-carbonyl>methyl>-N-(4-methoxyphenyl)butanamide 在 copper diacetate 、 叔丁基锂 、 四苯基溴化膦 作用下， 生成 cis-4-(tert-butoxycarbonyl)-3-(N,N-dibenzylamino)-1-(4-methoxyphenyl)-2-azetidinone 、 3-ethyl-4<(S)-2-oxo-4-isopropyloxazoline-3-carbonyl>-1-(4-methoxyphenyl)-2-azetidinone
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by oxidative coupling of dianions of acyclic tertiary amides

  摘要：

  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.

  DOI：

  10.1021/jo00032a047
• 作为产物：
  描述：

  (+)-(4S)-3-bromoacetyl-4-(1-methylethyl)-2-oxazolidinone 在 三乙胺 作用下， 生成 N-<<(S)-2-oxo-4-isopropyloxazoline-3-carbonyl>methyl>-N-(4-methoxyphenyl)butanamide
  参考文献：
  名称：

  Stereoselective synthesis of .beta.-lactams by oxidative coupling of dianions of acyclic tertiary amides

  摘要：

  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.

  DOI：

  10.1021/jo00032a047

文献信息

• 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.