(4R,5S,6S)-3-[(3S,5S)-1-Allyloxycarbonyl-5-(4-trifluoromethyl-pyrimidin-2-ylsulfanylmethyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester | 372146-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (4R,5S,6S)-3-[(3S,5S)-1-Allyloxycarbonyl-5-(4-trifluoromethyl-pyrimidin-2-ylsulfanylmethyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
• CAS: 372146-89-9
• 化学式: C₂₇H₃₁F₃N₄O₆S₂
• 分子量: 628.694
• InChiKey: CWYUJZOUNNEEQL-NGDUPAHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  122.16
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S)-3-[(3S,5S)-1-Allyloxycarbonyl-5-(4-trifluoromethyl-pyrimidin-2-ylsulfanylmethyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 在 四(三苯基膦)钯 、 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[[4-(trifluoromethyl)pyrimidin-2-yl]sulfanylmethyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[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：

  4-(三氟甲基)-2-巯基嘧啶 在 sodium hydroxide 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 8.33h， 生成 (4R,5S,6S)-3-[(3S,5S)-1-Allyloxycarbonyl-5-(4-trifluoromethyl-pyrimidin-2-ylsulfanylmethyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-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