diphenylmethyl (6R,7R)-7-isocyano-3-methylceph-3-em-4-carboxylate | 52681-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diphenylmethyl (6R,7R)-7-isocyano-3-methylceph-3-em-4-carboxylate
• 英文别名: Diphenylmethyl (6R, 7R)-7-Isocyano-3-methylceph-3-em-4-carboxylate；benzhydryl (6R,7R)-7-isocyano-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 52681-36-4
• 化学式: C₂₂H₁₈N₂O₃S
• 分子量: 390.463
• InChiKey: AAROKVHSCFETFZ-DYESRHJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diphenylmethyl (6R,7R)-7-isocyano-3-methylceph-3-em-4-carboxylate 在 溴 、 三氟乙酸 作用下， 以 四氢呋喃 、 四氯化碳 、 甲苯 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and .beta.-lactamase stability on the pKa of the C-7 heterocycle

  摘要：

  Cephalosporins with new aminobenzimidazole and aminoimidazoline heterocycles at C-7 have been synthesized starting with versatile C-7 isocyanide dihalide synthons. The aminobenzimidazoles have a broad spectrum of antibacterial activity, including Gram-positive and Gram-negative organisms, but possess limited beta-lactamase stability. In contrast, the aminoimidazolines have a narrow spectrum of antibacterial activity, limited to Gram-negative strains only, but possess outstanding beta-lactamase stability. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-7 amino heterocycle, basic C-7 residues giving cephalosporins with exceptional beta-lactamase stability.

  DOI：

  10.1021/jm00107a035
• 作为产物：
  描述：

  光气 、 diphenylmethyl(6R,7R)-7-formamido-3-methylceph-3-em-4-carboxylate 、 吡啶 在 水 、 乙酸乙酯 、 petroleum-ether 作用下， 以 二氯甲烷 为溶剂， 以to give the title compound as a pale-pink solid (9.539 g., 24.4 mmole, 81.5%)的产率得到diphenylmethyl (6R,7R)-7-isocyano-3-methylceph-3-em-4-carboxylate
  参考文献：
  名称：

  7.beta.-Isocyano cephalosporin esters and process of preparation

  摘要：

  提供了6.beta.-异氰酸基青霉素和7.beta.-异氰酸基头孢菌素酯作为合成青霉素和头孢菌素类抗生素的中间体。这些新化合物可通过将相应的6.beta.-甲酰胺基青霉素酯或7.beta.-甲酰胺基头孢菌素酯与由磷、硫或碳或这些元素的氧酸衍生的酸卤化物反应来制备，适当的卤化物包括亚砜氯化物或光气，或与三苯基膦和卤代烃（如四氯化碳）等三价磷化合物反应。还描述了通过在酸性条件下与芳香醛反应，然后用水介质处理，将新产品转化为6.beta.-和7.beta.-（.alpha.-羟基）芳基乙酰胺基青霉素和头孢菌素的过程。

  公开号：

  US03974150A1

文献信息

• Antibiotics
  申请人：Glaxo Laboratories Limited

  公开号：US04020077A1

  公开（公告）日：1977-04-26

  Novel 6.beta.-isocyano penicillin and 7.beta.-isocyano cephalosporin esters of value as intermediates in the synthesis of penicillin and cephalosporin antibiotics are provided. The novel compounds may be prepared by reaction of the corresponding 6.beta.-formamido penicillin ester or 7.beta.-formamido cephalosporin ester with an acid halide derived from phosphorus, sulphur or carbon or from an oxygen acid of one of said elements, suitable halides including thionyl chloride or phosgene, or with a trivalent phosphorus compound such as triphenylphosphine and a halogenated hydrocarbon such as carbon tetrachloride. The conversion of the novel products to 6.beta.- and 7.beta.-(.alpha.-hydroxy) arylacetamido penicillins and cephalosporins respectively by reaction under acidic conditions with an aromatic aldehyde followed by treatment with an aqueous medium is also described.

  提供了6.beta.-异氰酸基青霉素和7.beta.-异氰酸基头孢菌素酯作为合成青霉素和头孢菌素抗生素中间体的新化合物。可以通过将相应的6.beta.-甲酰胺青霉素酯或7.beta.-甲酰胺头孢菌素酯与来自磷、硫或碳或这些元素的氧酸的酸卤反应来制备新化合物，适当的卤化物包括亚磺酰氯或光气，或者与三苯基膦和卤代烃（如四氯化碳）等三价磷化合物反应。本文还描述了将新产品在酸性条件下与芳香醛反应，然后用水介质处理，将其转化为6.beta.-和7.beta.-(.alpha.-羟基)芳基乙酰胺青霉素和头孢菌素的过程。