(2S,4S)-2-[(Z)-2-(3-Hydroxymethyl-isoxazol-5-yl)-vinyl]-4-mercapto-pyrrolidine-1-carboxylic acid allyl ester | 326605-40-7

• 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)-2-[(Z)-2-(3-Hydroxymethyl-isoxazol-5-yl)-vinyl]-4-mercapto-pyrrolidine-1-carboxylic acid allyl ester
• CAS: 326605-40-7
• 化学式: C₁₄H₁₈N₂O₄S
• 分子量: 310.374
• InChiKey: IYHAUYVBLOVMAN-ZMQQHQCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.8
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2-[(Z)-2-(3-Hydroxymethyl-isoxazol-5-yl)-vinyl]-4-mercapto-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 乙腈 为溶剂， 反应 2.0h， 生成 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(3S,5S)-5-[(Z)-2-(3-hydroxymethyl-isoxazol-5-yl)-vinyl]-pyrrolidin-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological activity of 1β-methyl-2-[5′-isoxazoloethenylpyrrolidin-3′-ylthio]carbapenems

  摘要：

  A new series of 1 beta -methylcarbapenems 1a-i bearing isoxazoloethenyl groups on the pyrrolidine ring has been prepared and evaluated for in vitro antibacterial activity and stability to DHP-I. Most compounds showed excellent antibacterial activity and high stability to DHP-I superior to that of meropenem. Of these new carbapenems, 1a,b,h exhibited the best combination of antibacterial activity and DHP-I stability. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00575-8
• 作为产物：
  描述：

  5-[(E)-2-((2S,4R)-1-Allyloxycarbonyl-4-methanesulfonyloxy-pyrrolidin-2-yl)-vinyl]-isoxazole-3-carboxylic acid methyl ester 在 甲醇 、 sodium hydroxide 、 sodium tetrahydroborate 、 乙醇 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 12.0h， 生成 (2S,4S)-2-[(Z)-2-(3-Hydroxymethyl-isoxazol-5-yl)-vinyl]-4-mercapto-pyrrolidine-1-carboxylic acid allyl ester
  参考文献：
  名称：

  Synthesis and biological activity of 1β-methyl-2-[5′-isoxazoloethenylpyrrolidin-3′-ylthio]carbapenems

  摘要：

  A new series of 1 beta -methylcarbapenems 1a-i bearing isoxazoloethenyl groups on the pyrrolidine ring has been prepared and evaluated for in vitro antibacterial activity and stability to DHP-I. Most compounds showed excellent antibacterial activity and high stability to DHP-I superior to that of meropenem. Of these new carbapenems, 1a,b,h exhibited the best combination of antibacterial activity and DHP-I stability. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00575-8