bis(1-formylpyrazolidin-4-yl) disulfide | 141518-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: bis(1-formylpyrazolidin-4-yl) disulfide
• 英文别名: 4-[(1-Formylpyrazolidin-4-yl)disulfanyl]pyrazolidine-1-carbaldehyde
• CAS: 141518-02-7
• 化学式: C₈H₁₄N₄O₂S₂
• 分子量: 262.357
• InChiKey: LOVWWBSGTQSDGF-UHFFFAOYSA-N

物化性质

• 沸点：
  430.5±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(1-formylpyrazolidin-4-yl) disulfide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以85%的产率得到bis(4-pyrazolidinyl) disulfide dihydrochloride
  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：

  1-formyl-4-mercaptopyrazolidine 在 air 、 三氯化铁 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到bis(1-formylpyrazolidin-4-yl) disulfide
  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

• Process for preparing 1,2-pyrazolidine-4-yl-disulfide compound
  申请人：WAKO PURE CHEMICAL INDUSTRIES LTD

  公开号：EP0641783A1

  公开（公告）日：1995-03-08

  Novel and improved simple process for preparing a 1,2-pyrazolidine-4-yl-disulfide compound represented by the following formula:    wherein R¹ and R² are, independently each other, a hydrogen atom or an amino-protecting group. This compound may be prepared by reacting a compound of the formula:    wherein R³ is an acid anion residue group, and    R¹ and R² have the same meanings as above, with a disulfide compound selected from the group consisting of an alkali metal disulfide, an alkali earth metal disulfide, an ammonium disulfide and a tri-alkylammonium disulfide.

  制备下式所代表的 1,2-吡唑烷-4-基二硫化物化合物的新颖而改进的简单工艺： 其中 R¹ 和 R² 互不独立地为氢原子或氨基保护基团。 该化合物可通过反应式如下的化合物制备： 其中 R³ 是酸阴离子残基，且 R¹ 和 R² 的含义同上，与选自碱金属二硫化物、碱土金属二硫化物、二硫化铵和三烷基二硫化铵组成的组的二硫化物化合物反应。
• US5463075A
  申请人：——

  公开号：US5463075A

  公开（公告）日：1995-10-31