(4S,2'S)-3β-bromo-3-methyl-7β-(phenoxyacetamido)-4-spiro-4'-<2'-methoxy-2'-(p-nitrophenyl)-1',3'-dioxolane>cepham | 132645-20-6

• 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: (4S,2'S)-3β-bromo-3-methyl-7β-(phenoxyacetamido)-4-spiro-4'-<2'-methoxy-2'-(p-nitrophenyl)-1',3'-dioxolane>cepham
• 英文别名: (4S,2'S)-3β-bromo-3-methyl-7β-(phenoxyacetamido)-4-spiro-4'-[2'-methoxy-2'-(p-nitrophenyl)-1',3'-dioxolane]cepham
• CAS: 132645-20-6；132746-29-3
• 化学式: C₂₄H₂₄BrN₃O₈S
• 分子量: 594.44
• InChiKey: LTMXETSTHCLTSS-ZJFHNGKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  129.47
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (4S,2'S)-3β-bromo-3-methyl-7β-(phenoxyacetamido)-4-spiro-4'-<2'-methoxy-2'-(p-nitrophenyl)-1',3'-dioxolane>cepham 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 24.0h， 以37%的产率得到(4R,2'S)-3-methyl-7β-(phenoxyacetamido)-4-spiro-4'-<2'-methoxy-2'-(p-nitrophenyl)-1',3'-dioxolane>-2-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
• 作为产物：
  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