3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester | 6187-87-7

• 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: 3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
• 英文别名: t-butyl 7-aminocephalosporanate；t-butyl 3-acetyloxymethyl-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；(6R)-3-acetoxymethyl-7t-amino-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester；7β-amino-cephalosporanic acid tert-butyl ester；3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, tert-butyl ester；3-(Acetyloxy)methyl-7-amino-8-oxo-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester；tert-butyl 3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 6187-87-7；102253-55-4
• 化学式: C₁₄H₂₀N₂O₅S
• 分子量: 328.389
• InChiKey: SKVHPNQACYIQDC-UHFFFAOYSA-N

物化性质

• 沸点：
  506.2±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 在 对甲苯磺酸 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (R)-3-acetoxymethyl-7-diazo-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  C7烷基化的7-脱氨基头孢菌素衍生物的合成。

  摘要：

  DOI：

  10.1021/jo00871a020
• 作为产物：
  描述：

  7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid 以 7-氨基去乙酰氧基头孢烷酸 为溶剂， 生成 7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid t-butyl ester 、 3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  7-(2,3-Dihydrobenzo-5-furanyl)-acetamido cephalosporin derivatives

  摘要：

  这项发明涉及新的7-(2,3-二氢苯并-5-呋喃基)乙酰胺头孢菌素衍生物及其制备方法。

  公开号：

  US04229575A1

文献信息

• Substituted cephalosporin sulfones as anti-inflammatory and
  申请人：Merck & Co., Inc.

  公开号：US04547371A1

  公开（公告）日：1985-10-15

  Substituted cephalosporin sulfones are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.

  替代头孢菌素磺酮被发现是有效的弹性蛋白酶抑制剂，因此可用作抗炎/抗变性剂。
• 7-[[Amino(1,3-dihydrobenzo[c]thienyl)acetyl]amino]cephalosporin
  申请人：Richardson-Merrell Inc.

  公开号：US04219648A1

  公开（公告）日：1980-08-26

  This invention is directed to new 7-[[amino(1,3-dihydrobenzo[c]thien-5-yl)acetyl]amino]cephalosporin derivatives useful as antibiotics.

  这项发明涉及新的7-[[氨基(1,3-二氢苯并[c]噻吩-5-基)乙酰]氨基]头孢菌素衍生物，可用作抗生素。
• Cephalosporin derivatives
  申请人：Yeda Research and Development Co. Ltd.

  公开号：US04180660A1

  公开（公告）日：1979-12-25

  New cephalosporin derivatives containing a formyl substituted pyrrole group and the processes for preparing same are described.

  描述了含有一个甲酰基取代的吡咯基团的新头孢菌素衍生物及其制备过程。
• Antibacterial cephalosporin compounds
  申请人：Hoffmann La Roche Inc.

  公开号：US05189157A1

  公开（公告）日：1993-02-23

  There are presented antibacterial cephalosporins having broad antimicrobial activity as well as intermediates for their formation, such compounds having the formula ##STR1## wherein X is ##STR2## R is hydrogen or a carboxylic acid protecting group; R.sub.1 is hydrogen or an acyl group; R.sub.2 is hydrogen or lower alkoxy; and R.sub.3 is carbocyclic aryl or alkyl carbocyclic aryl substituted on the ring with two or more of hydroxy and/or lower alkanoyl ester groups, with halogen being an optional additional ring substituent; as well as the corresponding readily hydrolyzable esters, pharmaceutically acceptable salts and hydrates of these compounds where R is hydrogen.

  提供了具有广谱抗微生物活性的抗菌头孢菌素以及其形成的中间体，该化合物具有以下式子：##STR1## 其中X为##STR2## R为氢或羧酸保护基；R.sub.1为氢或酰基；R.sub.2为氢或较低的烷氧基；R.sub.3为环烷基芳基或取代环上的两个或更多羟基和/或较低的烷酰基酯基的烷基环烷基芳基，其中卤素是可选的额外环取代基；以及这些化合物的相应容易水解的酯，药学上可接受的盐和水合物，其中R为氢。
• Cephalosporin derivatives, and compositions containing them
  申请人：Rhone-Poulenc Industries

  公开号：US04034088A1

  公开（公告）日：1977-07-05

  New cephalosporin derivatives of the general formula: ##STR1## in which R represents a straight or branched chain C.sub.1-4 alkyl radical, or a phenyl (straight or branched chain C.sub.1-4 alkyl) radical, n is 0, 1 or 2, and either R.sub.1 is a pyridinio ion and R.sub.2 is a carboxylato ion, or R.sub.1 represents a hydrogen atom, or an acetoxy, (5-methyl-1,3,4-thiadiazol-2-yl)-thio or (1-methyl-1,2,3,4-tetrazol-5-yl)-thio radical and R.sub.2 represents a carboxy radical or a radical of the formula; ##STR2## in which the radical: ##STR3## is a radical which can be removed easily by enzymatic means and in which R.sub.3 represents a hydrogen atom or a straight or branched chain C.sub.1-4 alkyl radical, a phenyl radical or a phenyl (C.sub.1-2 alkyl) radical and R.sub.4 represents a straight or branched chain C.sub.1-4 alkyl radical, a straight or branched chain C.sub.1-4 alkoxy radical, a cyclohexyl radical, a phenyl radical or a phenyl (C.sub.1-2 alkyl) radical; With the proviso that when R is an alkyl radical and either R.sub.1 is a hydrogen atom or an acetoxy radical and R.sub.2 is a carboxy radical or R.sub.1 is a pyridinio ion and R.sub.2 is a carboxylato ion, n is 1 or 2, and metal salts thereof and addition salts thereof with nitrogen-containing bases are new compounds; they possess valuable antibacterial properties, showing activity against both Gram-positive and Gram-negative bacteria.

  新的头孢菌素衍生物的一般式为：##STR1## 其中R代表直链或支链C.sub.1-4烷基基团，或苯基（直链或支链C.sub.1-4烷基）基团，n为0、1或2，且R.sub.1为吡啶离子，R.sub.2为羧酸根离子，或R.sub.1代表氢原子，或乙酰氧基，(5-甲基-1,3,4-噻二唑-2-基)-硫基或(1-甲基-1,2,3,4-四唑-5-基)-硫基基团，R.sub.2代表羧基基团或公式的基团：##STR2## 其中基团：##STR3## 是一种易于通过酶的手段去除的基团，且R.sub.3代表氢原子或直链或支链C.sub.1-4烷基基团、苯基基团或苯基（C.sub.1-2烷基）基团，R.sub.4代表直链或支链C.sub.1-4烷基基团、直链或支链C.sub.1-4烷氧基基团、环己基基团、苯基基团或苯基（C.sub.1-2烷基）基团；但当R为烷基基团且R.sub.1为氢原子或乙酰氧基，R.sub.2为羧基基团或R.sub.1为吡啶离子且R.sub.2为羧酸根离子时，n为1或2，其金属盐及其与含氮碱的加合物是新的化合物；它们具有有价值的抗菌性能，对革兰氏阳性和革兰氏阴性细菌均有活性。