bis(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl) disulfide dichloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: bis(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl) disulfide dichloride
• 化学式: C₁₀H₁₄N₆S₂*2Cl
• 分子量: 353.299
• InChiKey: WYCRECRRDKPMHC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  bis(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl) disulfide dichloride 在 三丁基膦 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 phosphate buffer 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 4.0h， 生成 比阿培南
  参考文献：
  名称：

  New Straightforward Synthesis and Characterization of a Unique 1β-Methylcarbapenem Antibiotic Biapenem Bearing a σ-Symmetric Bicyclotriazoliumthio Group as the Pendant Moiety

  摘要：

  Biapenem 1, (1R,5S,6S,)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)thio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate, is a new non-natural 1 beta-methylcarbapenem antibiotic which exhibits a wide range of antibacterial activity, remarkable chemical stability, and extensive stability against human renal dehydropeptidase-I. Mercaptobicyclotriazolium chloride 2 useful for the pendant moiety of 1 was successfully synthesized starting from hydrazine hydrate 3 along an economically available synthetic route. The thiol 2 was efficiently exploited for an expeditious synthesis of biapenem 1. Characterization (crystal structure, nonbonded S---O interaction, conformational analysis, and CH- - -O hydrogen bonds) of 1 was investigated by its X-ray crystallographic, H-1 NMR, and deuteration experiment analyses.

  DOI：

  10.1021/jo980462j
• 作为产物：
  描述：

  bis(1-formylpyrazolidin-4-yl) disulfide 在 盐酸 、 potassium hydrogencarbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 6.17h， 生成 bis(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl) disulfide dichloride
  参考文献：
  名称：

  New Straightforward Synthesis and Characterization of a Unique 1β-Methylcarbapenem Antibiotic Biapenem Bearing a σ-Symmetric Bicyclotriazoliumthio Group as the Pendant Moiety

  摘要：

  Biapenem 1, (1R,5S,6S,)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)thio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate, is a new non-natural 1 beta-methylcarbapenem antibiotic which exhibits a wide range of antibacterial activity, remarkable chemical stability, and extensive stability against human renal dehydropeptidase-I. Mercaptobicyclotriazolium chloride 2 useful for the pendant moiety of 1 was successfully synthesized starting from hydrazine hydrate 3 along an economically available synthetic route. The thiol 2 was efficiently exploited for an expeditious synthesis of biapenem 1. Characterization (crystal structure, nonbonded S---O interaction, conformational analysis, and CH- - -O hydrogen bonds) of 1 was investigated by its X-ray crystallographic, H-1 NMR, and deuteration experiment analyses.

  DOI：

  10.1021/jo980462j

文献信息

• 一种比阿培南中间体的制备方法
  申请人：邯郸市康瑞生物科技有限公司

  公开号：CN105566354A

  公开（公告）日：2016-05-11

  本发明涉及一种比阿培南中间体(比阿培南缩合物)及其制备方法，即(式I)的制备方法。本发明在混合溶剂中加入化合物双(6，7-二氢-5H-吡唑并[1，2-a][1，2，4]三唑-6-基)二硫二氯化物(式II)，不制备化合物6，7-二氢-6-巯基-5H-吡唑并[1，2-a][1，2，4]三唑内鎓氯化物(比阿培南侧链)(式III)，直接加入式IV化合物(4R，5S，6S)-3-二苯氧磷酰氧基-6-[1R-1-羟乙基]-4-甲基-7-氧代-1-氮杂双环[3，2，0]庚-2-烯-2羧酸对硝基苄酯(双环母核)，采用“一锅煮”的方法，制得比阿培南缩合物，提高了比阿培南缩合物的生产效率和收率，制得的比阿培南缩合物纯度高，可满足比阿培南的合成要求，所采用方法反应条件温和，安全，对环境没有污染，适合工业化生产。
• New Straightforward Synthesis and Characterization of a Unique 1β-Methylcarbapenem Antibiotic Biapenem Bearing a σ-Symmetric Bicyclotriazoliumthio Group as the Pendant Moiety
  作者：Toshio Kumagai、Satoshi Tamai、Takao Abe、Hiroshi Matsunaga、Kazuhiko Hayashi、Ikuo Kishi、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.1021/jo980462j

  日期：1998.11.1

  Biapenem 1, (1R,5S,6S,)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)thio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate, is a new non-natural 1 beta-methylcarbapenem antibiotic which exhibits a wide range of antibacterial activity, remarkable chemical stability, and extensive stability against human renal dehydropeptidase-I. Mercaptobicyclotriazolium chloride 2 useful for the pendant moiety of 1 was successfully synthesized starting from hydrazine hydrate 3 along an economically available synthetic route. The thiol 2 was efficiently exploited for an expeditious synthesis of biapenem 1. Characterization (crystal structure, nonbonded S---O interaction, conformational analysis, and CH- - -O hydrogen bonds) of 1 was investigated by its X-ray crystallographic, H-1 NMR, and deuteration experiment analyses.