N-<(tert-butoxycarbonyl)methyl>-N-(4-methoxyphenyl)-2-butenamide | 138924-33-1

• 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-<(tert-butoxycarbonyl)methyl>-N-(4-methoxyphenyl)-2-butenamide
• 英文别名: N-[(tert-butoxycarbonyl)methyl]-N-(4-methoxyphenyl)-2-butenamide；tert-butyl 2-(N-[(E)-but-2-enoyl]-4-methoxyanilino)acetate
• CAS: 138924-33-1
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: AZTZPRRSCQAHCG-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  正丁基锂 、 N-<(tert-butoxycarbonyl)methyl>-N-(4-methoxyphenyl)-2-butenamide 在 N-碘代丁二酰亚胺 、 四苯基溴化膦 作用下， 生成 3,4-cis-4-(tert-butoxycarbonyl)-1-(4-methoxyphenyl)-3-(1-methylpentyl)-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：

  溴乙酸叔丁酯 在 苄基三乙基溴化铵 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 N-<(tert-butoxycarbonyl)methyl>-N-(4-methoxyphenyl)-2-butenamide
  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.