2-<(3-pyridinylcarbonyl)amino>ethyl 7-(2-thienylacetamido)cephalosporante Δ3 | 154777-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-<(3-pyridinylcarbonyl)amino>ethyl 7-(2-thienylacetamido)cephalosporante Δ3
• 英文别名: 2-<(3-pyridinylcarbonyl)amino>ethyl 7-(2-thienylacetamido)cephalosporante Δ³；2-[(3-pyridinylcarbonyl)amino]ethyl 7-(2-thienylacetamido)cephalosporante Δ³
• CAS: 154777-98-7
• 化学式: C₂₄H₂₄N₄O₇S₂
• 分子量: 544.609
• InChiKey: AQPYTFQNUUQJBM-AUSIDOKSSA-N

物化性质

• 沸点：
  910.9±65.0 °C(predicted)
• 密度：
  1.48±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  144.0
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-<(3-pyridinylcarbonyl)amino>ethyl 7-(2-thienylacetamido)cephalosporante Δ3 在 sodium dithionite 、 碳酸氢钠 作用下， 以 硝基甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 73.0h， 生成 2-<<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>amino>ethyl 7-(2-thienylacetamido)-cephalosporante
  参考文献：
  名称：

  Isomerism of Cephalosporin Esters; Theoretical and Practical Aspects

  摘要：

  Attempts to prepare 1,4-dihydropyridine targetor based chemical. delivery systems (CDS) for 7-(thiophene-2-acetamido) cephalosporanic acid (cephalotin) (1) are reported. Reaction of 1 with hydroxyethylnicotinamide resulted in a mixture of Delta(2) and Delta(3) isomers of the 3-pyridinylcarbonylamino esters of 1; after chromatographic separation the Delta(3) isomer was N-methylated and the resulting quaternary pyridinium salt was reduced with sodium dithionite to give the CDS. Attempts to attach the dihydropyridine moiety to 1 as an acyloxyalkyl ester failed. Relative stabilities of the Delta(3) and Delta(2) isomers of cephalotin acid and methyl ester, as reflected by theoretically (AM1 and PM3) calculated heats of formation (Delta H-f) indicated that kinetic and mechanistic, rather than thermodynamic factors are responsible for the isomerization of the esters.

  DOI：

  10.3987/com-93-s37
• 作为产物：
  描述：

  N-(2-羟乙基)烟酰胺 、 头孢噻吩 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 20.0h， 以35.9%的产率得到2-<(3-pyridinylcarbonyl)amino>ethyl 7-(2-thienylacetamido)cephalosporante Δ3
  参考文献：
  名称：

  Isomerism of Cephalosporin Esters; Theoretical and Practical Aspects

  摘要：

  Attempts to prepare 1,4-dihydropyridine targetor based chemical. delivery systems (CDS) for 7-(thiophene-2-acetamido) cephalosporanic acid (cephalotin) (1) are reported. Reaction of 1 with hydroxyethylnicotinamide resulted in a mixture of Delta(2) and Delta(3) isomers of the 3-pyridinylcarbonylamino esters of 1; after chromatographic separation the Delta(3) isomer was N-methylated and the resulting quaternary pyridinium salt was reduced with sodium dithionite to give the CDS. Attempts to attach the dihydropyridine moiety to 1 as an acyloxyalkyl ester failed. Relative stabilities of the Delta(3) and Delta(2) isomers of cephalotin acid and methyl ester, as reflected by theoretically (AM1 and PM3) calculated heats of formation (Delta H-f) indicated that kinetic and mechanistic, rather than thermodynamic factors are responsible for the isomerization of the esters.

  DOI：

  10.3987/com-93-s37