(2S,4S)-4-Mercapto-2-(pyrimidin-2-ylsulfanylmethyl)-pyrrolidine-1-carboxylic acid allyl ester | 372147-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,4S)-4-Mercapto-2-(pyrimidin-2-ylsulfanylmethyl)-pyrrolidine-1-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (2S,4S)-2-(pyrimidin-2-ylsulfanylmethyl)-4-sulfanylpyrrolidine-1-carboxylate
• CAS: 372147-04-1
• 化学式: C₁₃H₁₇N₃O₂S₂
• 分子量: 311.429
• InChiKey: WMMYRUDPNHMWRY-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-Mercapto-2-(pyrimidin-2-ylsulfanylmethyl)-pyrrolidine-1-carboxylic acid allyl ester 在 四(三苯基膦)钯 、 三正丁基氢锡 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-[(3S,5S)-5-(pyrimidin-2-ylsulfanylmethyl)-pyrrolidin-3-ylsulfanyl]-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological properties of new 1β-methylcarbapenems containing heteroaromatic thioether moiety

  摘要：

  The synthesis and biological activities of a series of new 1 beta -methylcarbapenems 1a-h having heteroaromatic thioether moiety at C-5 position of pyrrolidine were described. Among these compounds, 1,2,3-thiadiazole derivative 1h showed the most potent antibacterial activity and advanced pharmacokinetics in comparison with meropenem. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00451-6
• 作为产物：
  描述：

  (2S,4S)-4-Acetylsulfanyl-2-iodomethyl-pyrrolidine-1-carboxylic acid allyl ester 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 3.33h， 生成 (2S,4S)-4-Mercapto-2-(pyrimidin-2-ylsulfanylmethyl)-pyrrolidine-1-carboxylic acid allyl ester
  参考文献：
  名称：

  Synthesis and biological properties of new 1β-methylcarbapenems containing heteroaromatic thioether moiety

  摘要：

  The synthesis and biological activities of a series of new 1 beta -methylcarbapenems 1a-h having heteroaromatic thioether moiety at C-5 position of pyrrolidine were described. Among these compounds, 1,2,3-thiadiazole derivative 1h showed the most potent antibacterial activity and advanced pharmacokinetics in comparison with meropenem. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00451-6