(2S,4S)-4-Acetylsulfanyl-2-(4-trifluoromethyl-pyrimidin-2-ylsulfanylmethyl)-pyrrolidine-1-carboxylic acid allyl ester | 372146-98-0

• 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-Acetylsulfanyl-2-(4-trifluoromethyl-pyrimidin-2-ylsulfanylmethyl)-pyrrolidine-1-carboxylic acid allyl ester
• CAS: 372146-98-0
• 化学式: C₁₆H₁₈F₃N₃O₃S₂
• 分子量: 421.464
• InChiKey: BYTMLTRUBDYPHG-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.39
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-Acetylsulfanyl-2-(4-trifluoromethyl-pyrimidin-2-ylsulfanylmethyl)-pyrrolidine-1-carboxylic acid allyl ester 在 sodium hydroxide 、 四(三苯基膦)钯 、 三正丁基氢锡 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.33h， 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 、 (2S,4S)-4-Acetylsulfanyl-2-iodomethyl-pyrrolidine-1-carboxylic acid allyl ester 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 (2S,4S)-4-Acetylsulfanyl-2-(4-trifluoromethyl-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