4-methoxybenzyl (6R,7R)-7-phenylacetylamino-3-formyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4-methoxybenzyl (6R,7R)-7-phenylacetylamino-3-formyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• 英文别名: (4-methoxyphenyl)methyl (6R,7R)-3-formyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• 化学式: C₂₄H₂₂N₂O₆S
• 分子量: 466.514
• InChiKey: KBFIHWHARFHELG-NFBKMPQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  7-苯乙酰氨基-3-氯甲基-4-头孢烷酸对甲氧基苄酯 在 氧气 、 phosphorus pentoxide 、 sodium iodide 、 molybdenum(VI) oxide 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 4-methoxybenzyl (6R,7R)-7-phenylacetylamino-3-formyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Aerobic Oxidation of 3-Iodomethyl-Δ³-cephem-4-carboxylate to 3-Formyl-Δ³-cephem-4-carboxylate through 3-Hydroperoxymethyl-Δ³-cephem-4-carboxylate

  摘要：

  3-iodomethyl-8-oxo-7-phenylacetamido-5-thia-1-azabicyclo[4.2.在磷钼酸存在下，N-甲基-2-吡咯烷酮中的 3-碘甲基-8-氧代-7-苯乙酰胺基-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸酯（3-碘甲基-7-苯乙酰胺基-Δ3-cephem-4-羧酸酯）主要得到相应的 3-甲酰基-Δ3-cephem-4-羧酸酯，而在碘化钾存在下的类似有氧氧化则得到 3-羟甲基-Δ3-cephem-4-羧酸酯作为主要产物。3-hydroperoxymethyl-Δ3-cephem-4-carboxylate 作为有氧氧化的主要产物被分离出来，随后通过磷钼酸脱水转化为 3-formyl-Δ3-cephem-4-carboxylate 或通过碘化钾还原转化为 3-hydroxymethyl-Δ3-cephem-4-carboxylate 。

  DOI：

  10.1246/bcsj.69.229

文献信息

• New process for the manufacture of cephalosporin derivatives
  申请人：Basilea Pharmaceutica AG

  公开号：EP1067131B1

  公开（公告）日：2007-08-15
• TANAKA, HIDEO;TANIGUCHI, MASATOSHI;KAMEYAMA, YUTAKA;YAMAGUCHI, TAKEMA;SAS+, SYNLETT.,(1990) N1, C. 660-662
  作者：TANAKA, HIDEO、TANIGUCHI, MASATOSHI、KAMEYAMA, YUTAKA、YAMAGUCHI, TAKEMA、SAS+

  DOI：——

  日期：——
• US6384214B1
  申请人：——

  公开号：US6384214B1

  公开（公告）日：2002-05-07
• Aerobic Oxidation of 3-Iodomethyl-<i>Δ</i>³-cephem-4-carboxylate to 3-Formyl-<i>Δ</i>³-cephem-4-carboxylate through 3-Hydroperoxymethyl-<i>Δ</i>³-cephem-4-carboxylate
  作者：Hideo Tanaka、Ryo Kikuchi、Sigeru Torii

  DOI：10.1246/bcsj.69.229

  日期：1996.1

  Aerobic oxidation of p-methoxybenzyl 3-iodomethyl-8-oxo-7-phenylacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (3-iodomethyl-7-phenylacetamido-Δ3-cephem-4-carboxylate) in N-methyl-2-pyrrolidone in the presence of phosphomolybdic acid mainly afforded the corresponding 3-formyl-Δ3-cephem-4-carboxylate, while similar aerobic oxidation in the presence of potassium iodide gave 3-hydroxymethyl-Δ3-cephem-4-carboxylate as a major product. 3-Hydroperoxymethyl-Δ3-cephem-4-carboxylate was isolated as a primary product in the aerobic oxidation, which was subsequently converted to either 3-formyl-Δ3-cephem-4-carboxylate by dehydration with phosphomolybdic acid or 3-hydroxymethyl-Δ3-cephem-4-carboxylate by reduction with potassium iodide.

  3-iodomethyl-8-oxo-7-phenylacetamido-5-thia-1-azabicyclo[4.2.在磷钼酸存在下，N-甲基-2-吡咯烷酮中的 3-碘甲基-8-氧代-7-苯乙酰胺基-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸酯（3-碘甲基-7-苯乙酰胺基-Δ3-cephem-4-羧酸酯）主要得到相应的 3-甲酰基-Δ3-cephem-4-羧酸酯，而在碘化钾存在下的类似有氧氧化则得到 3-羟甲基-Δ3-cephem-4-羧酸酯作为主要产物。3-hydroperoxymethyl-Δ3-cephem-4-carboxylate 作为有氧氧化的主要产物被分离出来，随后通过磷钼酸脱水转化为 3-formyl-Δ3-cephem-4-carboxylate 或通过碘化钾还原转化为 3-hydroxymethyl-Δ3-cephem-4-carboxylate 。