(E)-methyl-5-carboxy-6-methyl-6-sulfono-4-aza-2-heptenoate | 98380-72-4

• 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: (E)-methyl-5-carboxy-6-methyl-6-sulfono-4-aza-2-heptenoate
• 英文别名: methyl 5-carboxy-6-methyl-6-sulfino-4-aza-2-heptenoate；2-[[(E)-3-methoxy-3-oxoprop-1-enyl]amino]-3-methyl-3-sulfinobutanoic acid
• CAS: 98380-72-4；98380-74-6
• 化学式: C₉H₁₅NO₆S
• 分子量: 265.287
• InChiKey: GTLBEYDAPVFCSH-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.28
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  112.93
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  舒巴坦酸 、 甲醇 生成 (E)-methyl-5-carboxy-6-methyl-6-sulfono-4-aza-2-heptenoate
  参考文献：
  名称：

  HAGINAKA, JUN;WAKAI, JUNKO;YASUDA, HIROYUKI;UNO, TOYOZO;NAKAGAWA, TERUMIC+, CHEM. AND PHARM. BULL., 1985, 33, N 5, 2035-2043

  摘要：

  DOI：

文献信息

• Alkaline degradation of sulbactam.
  作者：JUN HAGINAKA、JUNKO WAKAI、HIROYUKI YASUDA、TOYOZO UNO、TERUMICHI NAKAGAWA

  DOI：10.1248/cpb.33.2035

  日期：——

  Alkaline degradation of sodium sulbactam in methanol and in an aqueous solution has been investigated. The degradation in alkaline methanol produced methyl 5-carboxy-6-methyl-6-sulfino-4-aza-2-heptenoate (II) which showed an ultraviolet (UV) absorption maximum at 279 nm. The UV absorption almost disappeared when the solution was acidified with methanolic HCl solution, and reappeared on subsequent realkalization, suggesting interconversion between II and its protonated form. The degradation in aqueous alkaline solutions yielded 5-carboxy-6-methyl-6-sulfino-4-aza-2-heptenoic acid (IV), which showed λmax at 267 nm. IV was further degraded to 2-amino-3-methyl-3-sulfinobutanoic acid and formylacetic acid. The UV absorption of II and IV almost disappeared in aqueous acidic conditions, and reappeared on subsequent realkalization. These changes could be due to the hydrolysis of enamines II and IV to yield methyl formylacetate and formylacetic acid, respectively, in acidic conditions, and to the generation of the corresponding enolate ions on realkalization.

  已经研究了舒巴坦钠在甲醇和水溶液中的碱降解。在碱性甲醇中降解产生 5-羧基-6-甲基-6-亚磺基-4-氮杂-2-庚烯酸甲酯 (II)，其在 279 nm 处显示出最大紫外线 (UV) 吸收。当溶液用盐酸甲醇溶液酸化时，紫外吸收几乎消失，并在随后的再碱化中重新出现，表明 II 与其质子化形式之间发生了相互转化。在碱性水溶液中降解产生 5-羧基-6-甲基-6-亚磺基-4-氮杂-2-庚烯酸 (IV)，其在 267 nm 处显示 λmax。 IV进一步降解为2-氨基-3-甲基-3-亚磺基丁酸和甲酰乙酸。 II 和 IV 的紫外吸收在酸性水溶液条件下几乎消失，并在随后的再碱化中重新出现。这些变化可能是由于烯胺 II 和 IV 在酸性条件下分别水解产生甲酰乙酸甲酯和甲酰乙酸，以及在再碱化时生成相应的烯醇离子。
• Reaction products of sulbactam with pyrazole, 1,2,4-triazole and imidazole: High-performance liquid chromatographic behavior and structural investigation.
  作者：JUN HAGINAKA、JUNKO WAKAI、HIROYUKI YASUDA、TOYOZO UNO、TERUMICHI NAKAGAWA

  DOI：10.1248/cpb.33.4923

  日期：——

  The reactions of sulbactam (I) with pyrazole, 1, 2, 4-triazole and imidazole in weakly alkaline solutions yielded 1-(5-carboxy-6-methyl-6-sulfino-4-aza-2-heptenoyl)-pyrazole (III), -1, 2, 4-triazole (IV), and -imidazole (V), respectively. The proton nuclear magnetic resonance spectra and high-performance liquid chromatographic (HPLC) behavior indicate that III, IV and V each exist as a mixture of E- and Z-isomers in a ratio of about 2 : 1 in aqueous solutions at low temperature, and that rapid interconversion between the E- and Z-isomers occurs at high temperature. Compounds III, IV and V were converted to methyl 5-carboxy-6-methyl-6-sulfino-4-aza-2-heptenoate (II) in methanol.

  舒巴坦(I)与吡唑、1,2,4-三唑和咪唑在弱碱性溶液中反应生成1-(5-羧基-6-甲基-6-亚磺基-4-氮杂-2-庚烯酰基)-吡唑( III)、-1、2、4-三唑(IV)和-咪唑(V)。质子核磁共振谱和高效液相色谱（HPLC）行为表明，III、IV和V各自以E-和Z-异构体的混合物形式存在于低温水溶液中，比例约为2:1， E-异构体和Z-异构体之间的快速相互转化在高温下发生。将化合物III、IV和V在甲醇中转化为5-羧基-6-甲基-6-亚磺基-4-氮杂-2-庚烯酸甲酯(II)。