Cephaloridine epimer

• 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: Cephaloridine epimer
• 英文别名: 7-epicephaloridine；Aliporina；(6R,7S)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• 化学式: C₁₉H₁₇N₃O₄S₂
• 分子量: 415.494
• InChiKey: CZTQZXZIADLWOZ-MAUKXSAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Cephaloridine epimer 在 重水 作用下， 生成 头孢噻啶
  参考文献：
  名称：

  Alkaline hydrolysis of cephaloridine: An¹HNMR study. Temperature dependence of the rate constants

  摘要：

  AbstractA kinetic study on the basic hydrolysis of cephaloridine at pD= 10.5 was carried out by using the 1HNMR technique. Epimerization at H7, a nucleophilic attack of hydroxyl ion on the β‐lactam carbonyl group followed by the release of the pyridine molecule, and isomerization of the double bond at position 3 in the dihydrothiazine ring were the major reactions observed.Based on the results obtained, it should be emphasized that the presence of a pyridine group at 3′ results in a slightly increased formation constant for the exo methylene compound relative to other cephalosporins with different substituents at that position.The activation energy for the epimerization constant and the cleavage of the β‐lactam ring at pD 10.5 was 21.2 kcal/mol. © 1993 John Wiley & Sons, Inc.

  DOI：

  10.1002/kin.550251007
• 作为产物：
  描述：

  头孢噻啶 反应 1.0h， 生成 吡啶 、 (2R)-2-<(R)-carboxylato<(thien-2-yl)acetylamino>methyl>-5,6-dihydro-5-methylidene-1,3-thiazine-4-carboxylate 、 Δ²-cephaloridine 、 Cephaloridine epimer
  参考文献：
  名称：

  头孢噻啶在碱性水解反应中的降解

  摘要：

  使用离子对反相HPLC对头孢啶（1）在pH 10.5和37°的碱性水解进行了动力学研究。主所得降解产物，7-差向异构体2的1时，Δ 2异构体3的1，和3-亚甲基化合物4进行了鉴定。C（3 1）处的吡啶基团的存在会导致3-亚甲基化合物4和7-差向异构体2的形成常数略有增加，并引入新的反应：C（3）处的双键异构化在二氢噻嗪环中至C（2）。

  DOI：

  10.1002/hlca.19930760418

文献信息

• Degradation of Cephaloridine on Alkaline Hydrolysis
  作者：Bartolomé Vilanova、Francisco Muñoz、Josefa Donoso、Francisco Garcia-Blanco

  DOI：10.1002/hlca.19930760418

  日期：1993.6.30

  A kinetic study on the alkaline hydrolysis of cephaloridine (1) at pH 10.5 and 37° was carried out using ion-pair reversed-phase HPLC. The main resulting degradation products, the 7-epimer 2 of 1, the Δ2-isomer 3 of 1, and the 3-methylidene compound 4 were identified. The presence of a pyridinio group at C(31) results in a slightly increased formation constant for the 3-methylidene compound 4 and the

  使用离子对反相HPLC对头孢啶（1）在pH 10.5和37°的碱性水解进行了动力学研究。主所得降解产物，7-差向异构体2的1时，Δ 2异构体3的1，和3-亚甲基化合物4进行了鉴定。C（3 1）处的吡啶基团的存在会导致3-亚甲基化合物4和7-差向异构体2的形成常数略有增加，并引入新的反应：C（3）处的双键异构化在二氢噻嗪环中至C（2）。
• Alkaline hydrolysis of cephaloridine: An¹HNMR study. Temperature dependence of the rate constants
  作者：B. Vilanova、J. Donoso、F. Muñoz、F. García Blanco

  DOI：10.1002/kin.550251007

  日期：1993.10

  AbstractA kinetic study on the basic hydrolysis of cephaloridine at pD= 10.5 was carried out by using the 1HNMR technique. Epimerization at H7, a nucleophilic attack of hydroxyl ion on the β‐lactam carbonyl group followed by the release of the pyridine molecule, and isomerization of the double bond at position 3 in the dihydrothiazine ring were the major reactions observed.Based on the results obtained, it should be emphasized that the presence of a pyridine group at 3′ results in a slightly increased formation constant for the exo methylene compound relative to other cephalosporins with different substituents at that position.The activation energy for the epimerization constant and the cleavage of the β‐lactam ring at pD 10.5 was 21.2 kcal/mol. © 1993 John Wiley & Sons, Inc.