(6R)-3-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester | 28180-81-6

• 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: (6R)-3-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester
• 英文别名: p-Methoxybenzyl 3-methyl-7beta-phenoxyacetamidoceph-3-em-4-carboxylate；(4-methoxyphenyl)methyl (6R,7R)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 28180-81-6
• 化学式: C₂₄H₂₄N₂O₆S
• 分子量: 468.53
• InChiKey: GOOWUWBNUDMNOL-NFBKMPQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  p-Methoxybenzyl-7-(phenoxy-2-acetamido)-3-methylencepham-4-carboxylat 在 吡啶 、 三甲基氯硅烷 作用下， 反应 24.0h， 生成 (6R)-3-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester
  参考文献：
  名称：

  A facile synthesis of 7-amino-3-desacetoxycephalosporanic acid derivatives by indium-mediated reduction of 3-iodomethylcephems in aqueous media

  摘要：

  An efficient reductive conversion of 3-iodomethylcephalosporin and 3-acetoxymethylcephalosporin derivatives mediated by indium into the corresponding 3-methylcephems and 3-methylenecephams in moderate to good yields has been developed in an aqueous system. 3-Methylenecephams are converted into the corresponding 3-methylcephems under previously reported basic conditions quantitatively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00512-8

文献信息

• Process for the preparation of esters of N-blocked penicillin acids
  申请人：Glaxo Laboratories Limited

  公开号：US03960843A1

  公开（公告）日：1976-06-01

  A process is described for the preparation of esters of N-blocked amino acids (such as penicillins or cephalosporins) wherein the amino acid or a salt thereof is reacted with a primary amine and nitrosating agent.

  本文描述了一种制备N-保护氨基酸酯（如青霉素或头孢菌素）的过程，其中氨基酸或其盐与一种主要胺和亚硝酰化剂反应。
• US3960843A
  申请人：——

  公开号：US3960843A

  公开（公告）日：1976-06-01
• A facile synthesis of 7-amino-3-desacetoxycephalosporanic acid derivatives by indium-mediated reduction of 3-iodomethylcephems in aqueous media
  作者：Hyungsun Chae、Sangwon Cho、Gyochang Keum、Soon Bang Kang、Ae Nim Pae、Youseung Kim

  DOI：10.1016/s0040-4039(00)00512-8

  日期：2000.5

  An efficient reductive conversion of 3-iodomethylcephalosporin and 3-acetoxymethylcephalosporin derivatives mediated by indium into the corresponding 3-methylcephems and 3-methylenecephams in moderate to good yields has been developed in an aqueous system. 3-Methylenecephams are converted into the corresponding 3-methylcephems under previously reported basic conditions quantitatively. (C) 2000 Elsevier Science Ltd. All rights reserved.