7-amino<3-(2,3-cyclopentenopyridinium)methyl>ceph-3-em-4-carboxylate | 87314-56-5

• 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: 7-amino<3-(2,3-cyclopentenopyridinium)methyl>ceph-3-em-4-carboxylate
• 英文别名: 7-amino[3-(2,3-cyclopentenopyridinium)methyl]ceph-3-em-4-carboxylate；(6R,7R)-7-Amino-3-((6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；(6R,7R)-7-amino-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 87314-56-5
• 化学式: C₁₆H₁₇N₃O₃S
• 分子量: 331.395
• InChiKey: VEQQSGCBFQNSOF-IUODEOHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-amino<3-(2,3-cyclopentenopyridinium)methyl>ceph-3-em-4-carboxylate 在 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.5h， 生成 硫酸头孢匹罗
  参考文献：
  名称：

  One-Pot Synthesis of Cefpirome Sulfate from GCLE

  摘要：

  [image omitted] Cefpirome was synthesized in 37.7% overall yield from 3-chloromethyl-7-phenylacetylamino cephalosporanic acid p-methoxybenzyl ester (GCLE) by sequential substitution of C-3 chloride with iodide and 2,3-cyclopentenopyridine, followed by a one-pot procedure including deprotection of carboxyl group, hydrolysis of 7-phenylacetamido, and reaction with 2-mercaptobenzothiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate (MAEM). The reaction conditions were as follows: obtained from GCLE at low temperature (-5 to 0 degrees C) and absence of light, 3-iodomethyl-7-phenylacetylamino cephalosporanic acid p-methoxybenzyl ester (GILE) without purification was reacted directly with 2,3-cyclopentenopyridine, in which the molar ratio of GCLE, NaI, and 2,3-cyclopentenopyridine was 1:2:4, and the molar ratio of the resulting compound p-methoxybenzyl 7-phenylacetylamido-3-(2,3-cyclopenteno-1-pyridinio)methyl-3-cephem-4-carboxylate iodide and MAEM was 1:1.1. The structure of the intermediate and the target compound obtained were determined by nuclear magnetic resonance spectra and mass spectroscopy.

  DOI：

  10.1080/00397911003629499
• 作为产物：
  描述：

  7-苯乙酰氨基-3-氯甲基-4-头孢烷酸对甲氧基苄酯 在 青霉素(酰胺)酶 、 sodium iodide 、 苯酚 作用下， 以 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 9.5h， 生成 7-amino<3-(2,3-cyclopentenopyridinium)methyl>ceph-3-em-4-carboxylate
  参考文献：
  名称：

  One-Pot Synthesis of Cefpirome Sulfate from GCLE

  摘要：

  [image omitted] Cefpirome was synthesized in 37.7% overall yield from 3-chloromethyl-7-phenylacetylamino cephalosporanic acid p-methoxybenzyl ester (GCLE) by sequential substitution of C-3 chloride with iodide and 2,3-cyclopentenopyridine, followed by a one-pot procedure including deprotection of carboxyl group, hydrolysis of 7-phenylacetamido, and reaction with 2-mercaptobenzothiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate (MAEM). The reaction conditions were as follows: obtained from GCLE at low temperature (-5 to 0 degrees C) and absence of light, 3-iodomethyl-7-phenylacetylamino cephalosporanic acid p-methoxybenzyl ester (GILE) without purification was reacted directly with 2,3-cyclopentenopyridine, in which the molar ratio of GCLE, NaI, and 2,3-cyclopentenopyridine was 1:2:4, and the molar ratio of the resulting compound p-methoxybenzyl 7-phenylacetylamido-3-(2,3-cyclopenteno-1-pyridinio)methyl-3-cephem-4-carboxylate iodide and MAEM was 1:1.1. The structure of the intermediate and the target compound obtained were determined by nuclear magnetic resonance spectra and mass spectroscopy.

  DOI：

  10.1080/00397911003629499

文献信息

• Seibert; Klesel; Limbert, Arzneimittel-Forschung/Drug Research, 1983, vol. 33, # 8, p. 1084 - 1086
  作者：Seibert、Klesel、Limbert、et al.

  DOI：——

  日期：——
• LATTRELL, R.;DUERCKHEIMER, W.;KIRRSTETTER, R.;SCHWAB, W.
  作者：LATTRELL, R.、DUERCKHEIMER, W.、KIRRSTETTER, R.、SCHWAB, W.

  DOI：——

  日期：——
• One-Pot Synthesis of Cefpirome Sulfate from GCLE
  作者：Xuemin Duan、Yao Lu、Juan Han、Ligong Chen、Pengwu Zheng

  DOI：10.1080/00397911003629499

  日期：2011.2.7

  [image omitted] Cefpirome was synthesized in 37.7% overall yield from 3-chloromethyl-7-phenylacetylamino cephalosporanic acid p-methoxybenzyl ester (GCLE) by sequential substitution of C-3 chloride with iodide and 2,3-cyclopentenopyridine, followed by a one-pot procedure including deprotection of carboxyl group, hydrolysis of 7-phenylacetamido, and reaction with 2-mercaptobenzothiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate (MAEM). The reaction conditions were as follows: obtained from GCLE at low temperature (-5 to 0 degrees C) and absence of light, 3-iodomethyl-7-phenylacetylamino cephalosporanic acid p-methoxybenzyl ester (GILE) without purification was reacted directly with 2,3-cyclopentenopyridine, in which the molar ratio of GCLE, NaI, and 2,3-cyclopentenopyridine was 1:2:4, and the molar ratio of the resulting compound p-methoxybenzyl 7-phenylacetylamido-3-(2,3-cyclopenteno-1-pyridinio)methyl-3-cephem-4-carboxylate iodide and MAEM was 1:1.1. The structure of the intermediate and the target compound obtained were determined by nuclear magnetic resonance spectra and mass spectroscopy.