3-methyl-4-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)-3-cephem | 132645-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl-4-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)-3-cephem
• 英文别名: 3-methyl-4-{[(p-nitrobenzoyl)oxy]methyl}-7β-(phenoxyacetamido)-3-cephem
• CAS: 132645-19-3
• 化学式: C₂₃H₂₁N₃O₇S
• 分子量: 483.502
• InChiKey: QUWKTOLQEWFIBH-PSDZMVHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  128.08
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-methyl-4-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)-3-cephem 在 溴 、 calcium carbonate 作用下， 反应 0.5h， 以3.3%的产率得到3α-bromo-3β-methyl-4α-methoxy-4β-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)cepham
  参考文献：
  名称：

  Uncommon formation of spiro orthoesters in the bromomethoxylation reaction of a 4-[(aroyloxy)methyl]-3-cephem derivative

  摘要：

  The reaction of 4-[((p-nitrobenzoyl)oxy)methyl]-3-cephem derivative 4 with bromine in methanol afforded a mixture of the 3-bromo-4-methoxy adducts 5 and 6 and of the unexpected 4-spiro orthoesters 7 and 8. The structure and configuration of 7 and 8 were demonstrated through the determination of the solid-state structure of 7 and by H-1 and C-13 NMR studies and chemical transformations. The mechanism and the stereochemical outcome of the reaction are discussed.

  DOI：

  10.1021/jo00006a035
• 作为产物：
  描述：

  N-((R)-2-Hydroxymethyl-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-7-yl)-2-phenoxy-acetamide 、 4-硝基苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以74%的产率得到3-methyl-4-<((p-nitrobenzoyl)oxy)methyl>-7β-(phenoxyacetamido)-3-cephem
  参考文献：
  名称：

  Uncommon formation of spiro orthoesters in the bromomethoxylation reaction of a 4-[(aroyloxy)methyl]-3-cephem derivative

  摘要：

  The reaction of 4-[((p-nitrobenzoyl)oxy)methyl]-3-cephem derivative 4 with bromine in methanol afforded a mixture of the 3-bromo-4-methoxy adducts 5 and 6 and of the unexpected 4-spiro orthoesters 7 and 8. The structure and configuration of 7 and 8 were demonstrated through the determination of the solid-state structure of 7 and by H-1 and C-13 NMR studies and chemical transformations. The mechanism and the stereochemical outcome of the reaction are discussed.

  DOI：

  10.1021/jo00006a035