(6R)-3-(Hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 26296-27-5

• 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: (6R)-3-(Hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 26296-27-5
• 化学式: C₈H₉NO₄S
• 分子量: 215.23
• InChiKey: JWGFQCLMHAYABI-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

文献信息

• Cephalosporin intermediates and their preparation
  申请人：——

  公开号：EP0153874A3

  公开（公告）日：1986-08-13

  @ 3-(Activated ester)methyl-3-cephem 4-carboxylic acids are prepared by the direct reaction of a 3-hydroxymethyl-3-cephem-4-carboxylic acid with an activated-0-ester-methyl forming acylating agent, in the presence of a 4-(tertiary amino) pyridine catalyst and an acid-absorbing base, in a non-polar liquid solvent, at -78 to 30 C. Certain products of the reaction are novel.

  3- (活化酯)甲基-3-头孢-4-羧酸是通过 3-羟甲基-3-头孢-4-羧酸与活化的 0-酯甲基酰化剂在 4-(叔氨基)吡啶催化剂和吸酸碱存在下，在非极性液体溶剂中，于 -78 至 30 摄氏度下直接反应制备的。
• Hydroxymethylcephem compounds and their preparation
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0204517A2

  公开（公告）日：1986-12-10

  A process for preparing 7β-acylamino-3-hydroxy-methy)-3-cephem-4-carboxylic acids, optionally having 7 α-methoxy groups, or their alkali metal salts, comprises treating 7β-acylaminocephalosporanic acids (optionally having 7 α-methoxy groups) ortheir alkali metal salts with aqueous alkali metal hydroxides in lower alkanols.

  一种制备 7β-acylamino-3-hydroxy-methy)-3-cephem-4-carboxylic acids（可选具有 7 α-甲氧基基团）或其碱金属盐的工艺，包括在低级烷醇中用碱金属氢氧化物水溶液处理 7β-acylaminocephalosporanic acids（可选具有 7 α-甲氧基基团）或其碱金属盐。
• Method of producing cephem compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0230972A3

  公开（公告）日：1989-02-01

  A method of producing 3-alkanoyloxymethyl-3-cephem-4-­carboxylic acids, which are useful as antibiotics or as intermediates in the synthesis of antibiotics, by reacting a 3-hydroxymethyl-3-cephem-4-carboxylic acid with a saturated fatty acid anhydride in an aqueous medium in the presence of an acid-acceptor base and a 4-(tertiary amino)­pyridine.

  一种生产 3-烷酰氧基甲基-3-头孢-4-羧酸的方法，这种酸可用作抗生素或合成抗生素的中间体，其方法是在一种水介质中，在一种酸接受碱和一种 4-（叔氨基）吡啶的存在下，使一种 3-羟甲基-3-头孢-4-羧酸与一种饱和脂肪酸酸酐反应。
• Cephem compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0333082A2

  公开（公告）日：1989-09-20

  This invention provides a cephem compound of the formula (I): , wherein R¹ is an acyl group; R² is a carboxy group which may be esterified; R³ is hydrogen atom, a lower alkyl group or cyano group; R⁴ is hydrogen atom or a lower alkyl group ,or R⁴ together with R³ is a methylene chain having 2 or 3 carbon atoms; R⁵ is hydrogen atom or a lower alkyl group; A is an optionally substituted bivalent aromatic heterocyclic group which is bonded on the ring-constituting carbon atom with the adjacent sulfur atom; Y is a binding arm, sulfur or oxygen atom, -NH-, -CONH- or -NHCO-; Z is a binding arm or -NH-; m is an integer of 0 to 4 and n is an integer of 0 to 6, or a pharmacologically acceptable salt thereof, and a process for producing this compound.

  本发明提供了一种式(I)的头孢菌素化合物： 其中 R¹ 是酰基；R² 是可酯化的羧基；R³ 是氢原子、低级烷基或氰基；R⁴ 是氢原子或低级烷基，或 R⁴ 与 R³ 一起是具有 2 或 3 个碳原子的亚甲基链；R⁵ 是氢原子或低级烷基；A是任选取代的二价芳香杂环基团，其在成环碳原子上与相邻的硫原子键合；Y是结合臂、硫原子或氧原子、-NH-、-CONH-或-NHCO-；Z是结合臂或-NH-；m是0至4的整数，n是0至6的整数，或其药理学上可接受的盐，以及生产该化合物的工艺。
• Method for producing cephem compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0354538A2

  公开（公告）日：1990-02-14

  A method for producing 3-(3-oxobutyryloxymethyl)-3-­cephem-4-carboxylic acids which are antibiotics or intermediates for the synthesis of antibiotics, at a low temperature in a very short period of time and besides in good yield, characterized by reacting a 3-hydroxylmethyl-­3-cephem-4-carboxylic acid with diketene in the presence of a 4-(tertiary-amino)pyridine and if necessary, when a 7-acylamino-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxyl­ic acid is obtained, subjecting it to deacylation at the 7-position thereof.

  一种在低温、极短的时间内生产 3-(3-氧代丁酰氧甲基)-3-头孢-4-羧酸的方法，这种酸是抗生素或合成抗生素的中间体，而且收率高、其特征是：在 4-(叔氨基)吡啶存在下，使 3-羟甲基-3-头孢-4-羧酸与二乙烯反应，必要时，当得到 7-酰氨基-3-(3-氧代丁酰氧基甲基)-3-头孢-4-羧酸时，在其 7-位进行脱酰基反应。