(6R)-3-(5-carboxy-furan-2-ylmethyl)-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 36242-89-4

• 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-(5-carboxy-furan-2-ylmethyl)-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 英文别名: 3-(5-Carboxy-furfuryl)-7beta-phenylacetylamino-ceph-3-em-4-carboxylic acid；(6R,7R)-3-[(5-carboxyfuran-2-yl)methyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 36242-89-4
• 化学式: C₂₁H₁₈N₂O₇S
• 分子量: 442.449
• InChiKey: RCPSPKMNAWQBQZ-VQIMIIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid 在 sodium hydroxide 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 反应 4.0h， 生成 (6R)-3-(5-carboxy-furan-2-ylmethyl)-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  [7-氨基头孢菌酸的新衍生物。通过芳族部分取代乙酰基]。

  摘要：

  Abstract7‐Phenylacetamido‐3‐trifluoroacetoxymethyl‐ceph‐2‐em‐4‐carboxlic acid (7), which is easily produced from the iso‐cephalosporanic acid derivatives 4 or 6 by treatment with trifluoroacetic acid, reacts smoothly with ‘C‐nucleophiles’ to give derivatives of type 5 (Schema 1 and 2). Compounds 5 are converted into microbiologically active cephalosporins of type 8 (Table) by previously described methods.

  DOI：

  10.1002/hlca.19740570714

文献信息

• 3-R-methyl-7-amino-ceph-em-4-carboxylic acid compounds
  申请人：Ciba-Geigy Corporation

  公开号：US03932465A1

  公开（公告）日：1976-01-13

  3-R-Methyl-7-amino-ceph-2-em-4.xi.-carboxylic acid compounds, in which R is the C-residue of a C-nucleophilic compound are valuable intermediates, for example, in the manufacture of the corresponding 3-R-methyl-7-amino-ceph-3-em-4-carboxylic acid compounds with antibiotic properties.

  3-R-甲基-7-氨基-头孢-2-乙烯-4.xi.-羧酸化合物，其中R是C-亲核化合物的C-残基，是有价值的中间体，例如，在制造具有抗生素性质的相应的3-R-甲基-7-氨基-头孢-3-乙烯-4-羧酸化合物方面。
• US3932465A
  申请人：——

  公开号：US3932465A

  公开（公告）日：1976-01-13
• Neue Derivate der 7-Amino-cephalosporansäure. Über die Substitution der Acetoxygruppe durch aromatische Reste. Modifikationen von Antibiotica, 11. Mitteilung [1]
  作者：Heinrich Peter、Hermann Rodriguez、Beat Müller、Walter Sibral、Hans Bickel

  DOI：10.1002/hlca.19740570714

  日期：1974.11.6

  Abstract7‐Phenylacetamido‐3‐trifluoroacetoxymethyl‐ceph‐2‐em‐4‐carboxlic acid (7), which is easily produced from the iso‐cephalosporanic acid derivatives 4 or 6 by treatment with trifluoroacetic acid, reacts smoothly with ‘C‐nucleophiles’ to give derivatives of type 5 (Schema 1 and 2). Compounds 5 are converted into microbiologically active cephalosporins of type 8 (Table) by previously described methods.