4-methoxybenzyl 7β-phenylacetamido-3-methylenecepham-4-carboxylate | 101156-43-8

• 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: 4-methoxybenzyl 7β-phenylacetamido-3-methylenecepham-4-carboxylate
• 英文别名: 4-Methoxybenzyl 7beta-phenylacetamido-3-methylenecepham-4-carboxylate；(4-methoxyphenyl)methyl (6R,7R)-3-methylidene-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate
• CAS: 101156-43-8
• 化学式: C₂₄H₂₄N₂O₅S
• 分子量: 452.531
• InChiKey: OBWWNEFAZWSNIS-RAMXQINQSA-N

物化性质

• 沸点：
  713.4±60.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methoxybenzyl 7β-phenylacetamido-3-methylenecepham-4-carboxylate 在 吡啶 、 三甲基氯硅烷 作用下， 反应 24.0h， 生成 头孢克肟GENE杂质
  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
• 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 生成 4-methoxybenzyl 7β-phenylacetamido-3-methylenecepham-4-carboxylate
  参考文献：
  名称：

  TORII, SIGEHRU;TANAKA, XIDEHO;TANIGUTI, MASATOSI;SASAOKA, MITIO;SAJTO, NO+

  摘要：

  DOI：

文献信息

• Manufacture of cefalosporins and intermediates
  申请人：——

  公开号：US20040176590A1

  公开（公告）日：2004-09-09

  There is described a process for the preparation of 3-disubstituted cepham-4-carboxylic acid derivatives of formula I 1 wherein R″ is 4-methoxybenzyl, X is the residue of a thioether and Z is a residue of a nucleophilic compound and the conversion of these novel intermediates into the corresponding 3-cephem derivatives by oxidative cleavage of the mercaptan X-SH. By suitable deprotection, these 3-cephem derivatives afford cephalosporins such as ceftiofur, cefotaxime and ceftriaxone.

  描述了一种制备3-二取代头孢菌素-4-羧酸衍生物的过程，其化学式为I1，其中R″为4-甲氧基苄基，X为硫醚的残基，Z为亲核化合物的残基，并通过对巯基X-SH进行氧化裂解将这些新型中间体转化为相应的3-头孢菌素衍生物。通过适当的去保护作用，这些3-头孢菌素衍生物可制备头孢哌酮、头孢噻肟和头孢曲松等头孢菌素。
• Deprotection of carboxylic esters of .beta.-lactam homologs. Cleavage of p-methoxybenzyl, diphenylmethyl, and tert-butyl esters effected by a phenolic matrix
  作者：Sigeru Torii、Hideo Tanaka、Masatoshi Taniguchi、Yutaka Kameyama、Michio Sasaoka、Takashi Shiroi、Ryo Kikuchi、Ichiro Kawahara、Akihiro Shimabayashi、Shigemitsu Nagao

  DOI：10.1021/jo00011a034

  日期：1991.5

  p-Methoxybenzyl, diphenylmethyl, and tert-butyl esters were deprotected by gentle heating in phenol. This method of ester cleavage played an important role in beta-lactam synthesis. The mechanism of the reaction is believed to involve a proton relay through a hydrogen-bonded phenolic matrix.
• TORII, SIGEHRU;TANAKA, XIDEHO;TANIGUTI, MASATOSI;SASAOKA, MITIO;SAJTO, NO+
  作者：TORII, SIGEHRU、TANAKA, XIDEHO、TANIGUTI, MASATOSI、SASAOKA, MITIO、SAJTO, NO+

  DOI：——

  日期：——
• TORII, SIGERU;TANAKA, HIDEO;TANIGUCHI, MASATOSHI;KAMEYAMA, YUTAKA;SASAOKA+, J. ORG. CHEM., 56,(1991) N1, C. 3633-3637
  作者：TORII, SIGERU、TANAKA, HIDEO、TANIGUCHI, MASATOSHI、KAMEYAMA, YUTAKA、SASAOKA+

  DOI：——

  日期：——
• TORII, SIGERU;TANAKA, HIDEO;SASAOKA, MICHIO;KAMEYAMA, YUTAKA
  作者：TORII, SIGERU、TANAKA, HIDEO、SASAOKA, MICHIO、KAMEYAMA, YUTAKA

  DOI：——

  日期：——