(6R)-3-acetoxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; sodium salt | 26382-85-4

• 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-acetoxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; sodium salt
• 英文别名: 7β-(2-phenyl-acetylamino)-cephalosporanic acid; sodium salt；sodium salt of 7-(phenylacetamido)cephalosporanic acid；cephaloram sodium salt；7β-(Phenylacetamido)-cephalosporansaeure-natriumsalz；benzylcephalosporin; sodium salt；cephaloram; sodium salt；sodium;(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 26382-85-4
• 化学式: C₁₈H₁₇N₂O₆S*Na
• 分子量: 412.399
• InChiKey: MRRAOUWBTNKQGQ-SATBOSKTSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; sodium salt 在 β-Lactamase I 水 作用下， 生成
  参考文献：
  名称：

  Buckwell, Stephen C.; Page, Michael I.; Longridge, Jethro L., Journal of the Chemical Society. Perkin transactions II, 1988, p. 1823 - 1828

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酰氯 、 sodium 2-ethylhexanoic acid 生成 (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; sodium salt
  参考文献：
  名称：

  BUCKWELL, STEPHEN C.;PAGE, MICHAEL I.;WALEY, STEPHEN G.;LONGRIDGE, JETHRO+, J. CHEM. SOC. PERKIN TRANS.,(1988) N 10, C. 1815-1821

  摘要：

  DOI：

文献信息

• Cephalosporins
  申请人：Hoffmann-La Roche Inc.

  公开号：US04091211A1

  公开（公告）日：1978-05-23

  Cephalosporins represented by the formula X-S-Y wherein X is a deacetoxycephalosporinyl group and Y is a 6-membered heterocyclic group containing 1-3 nitrogens at least one of which is substituted and at least one of which is adjacent to a carbonyl group, said heterocyclic group containing one or more ring substituents and being characterized by being non-aromatic and not enolizable to an aromatic form.

  头孢菌素的结构式为X-S-Y，其中X是去乙酰头孢菌素基团，Y是含有1-3个氮原子的6元杂环基团，其中至少一个被取代，至少一个邻近一个羰基，所述杂环基团含有一个或多个环取代基，其特点是非芳香性且不能转变为芳香形式。
• Cephalosporanic acids. Part VI. Action of primary and secondary aromatic amines on cephalosporanic acids
  作者：J. Bradshaw、S. Eardley、A. G. Long

  DOI：10.1039/j39680000801

  日期：——

  molecules. 7-Phenylacetamido-cephalosporanic acid reacts in acetone at 50° with aniline, to give the lactam (V). This change represents initial nucleophilic attack at the 8-position; the dihydrothiazine (V) is protected by the stability of its γ-lactam system. The result is similar to the conversion of penicillanic acids into derivatives of the penicilloic acids.

  苯胺和茴香胺取代了7β-苯基乙酰氨基头孢烷酸（I； R 1 = NH·CO·CH 2 Ph，R 2 = OH，R 3 = OAc）中的乙酸酯基；如果不控制pH值，则产品可能会环化成γ-内酰胺（II）。如果pH值保持在7.5，则可防止环化。类似于戊二酸的乙烯基胺（III）是副产物。与N反应可避免内酰胺的形成取代的苯胺作为亲核试剂。我们没有观察到芳族分子的碳原子发生亲核攻击的产物。7-苯乙酰胺基-头孢烷酸在丙酮中与苯胺在50°下反应，生成内酰胺（V）。这种变化代表最初在8位发生亲核攻击；二氢噻嗪（V）受到其γ-内酰胺系统稳定性的保护。结果类似于青霉酸向青霉酸的衍生物的转化。
• Cephalosporanic acids. Part V. The action of bidentate nucleophiles on cephalosporanic acids
  作者：H. Fazakerley、D. A. Gilbert、G. I. Gregory、J. K. Lazenby、A. G. Long

  DOI：10.1039/j39670001959

  日期：——

  Certain thioamides convert cephalosporanic acids into 3-spirocephamoic acids. A two-stage process is suggested, exemplifying the reversible polarisability of the 3,4-double bond in the cephalosporanic acids. The first stage probably occurs in the anion, the second in the undissociated acid.

  某些硫代酰胺可将头孢烷酸转化为3-螺环乙酰胺酸。建议分两个阶段进行，以举例说明头孢烷酸中3,4-双键的可逆极化性。第一个阶段可能发生在阴离子中，第二个阶段发生在未解离的酸中。
• Reduction of cephalosporanic acids with chromium(II) salts
  作者：M. Ochiai、O. Aki、A. Morimoto、T. Okada、K. Morita

  DOI：10.1016/0040-4020(75)85004-6

  日期：1975.1

  7-Acylaminocephalosporanic acid derivatives (1) were converted into 7-acylamino-3-methylenecepham-4-carboxylic acids (2) by treatment with chromium(II) salts in aqueous media. The esters (4a or 4b) of 7-acylamino-3-methylenecepham compounds were readily isomerized to the 3-methyl-3-cephem compounds (5a or 5b) under basic conditions. The reaction mechanism is discussed.

  通过在水介质中用铬（II）盐处理，将7-酰基氨基头孢菌酸衍生物（1）转化为7-酰基氨基-3-亚甲基cepham -4-羧酸（2）。在碱性条件下，将7-酰基氨基-3-亚甲基cepham化合物的酯（4a或4b）容易异构化为3-甲基-3-cephem化合物（5a或5b）。讨论了反应机理。
• Process for the preparation of penicillin and cephalosporin sulfones
  申请人：ELI LILLY AND COMPANY

  公开号：EP0109818A2

  公开（公告）日：1984-05-30

  The process for preparing penicillin and cephalosporin sulfones by oxidation in an aqueous medium at pH between 4.0 to 6.5 of corresponding penicillin or cephalosporin or the sulfoxide thereof with potassium hydrogen persulfate.

  在 pH 值为 4.0 至 6.5 的水介质中，用过硫酸氢钾氧化相应的青霉素或头孢菌素或其亚砜，制备青霉素和头孢菌素砜的工艺。