N-(benzoylmethyl)-N-(4-methoxyphenyl)acetamide | 32156-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(benzoylmethyl)-N-(4-methoxyphenyl)acetamide
• 英文别名: N-(4-methoxy-phenyl)-N-(2-oxo-2-phenyl-ethyl)-acetamide；N-(4-methoxyphenyl)-N-phenacylacetamide
• CAS: 32156-60-8
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: SOVHNVWPHUCLGL-UHFFFAOYSA-N

物化性质

• 沸点：
  458.3±30.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(benzoylmethyl)-N-(4-methoxyphenyl)acetamide 生成 3-(4-methoxy-phenyl)-2-methyl-5-phenyl-oxazolium; iodide
  参考文献：
  名称：

  Thiazolocyanines

  摘要：

  DOI：

  10.1007/bf00480623
• 作为产物：
  描述：

  2-((4-methoxyphenyl)amino)-1-phenylethanone 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(benzoylmethyl)-N-(4-methoxyphenyl)acetamide
  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.
• Thiazolocyanines
  作者：E. D. Sych、O. V. Moreiko

  DOI：10.1007/bf00480623

  日期：1970.8