methyl (2S,3R,4R)-4-((4-bromophenyl)thio)-3-(2-methoxy-2-oxoethyl)-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxylate | 1290103-89-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,3R,4R)-4-((4-bromophenyl)thio)-3-(2-methoxy-2-oxoethyl)-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxylate
• CAS: 1290103-89-7
• 化学式: C₁₇H₁₇BrF₃NO₅S
• 分子量: 484.291
• InChiKey: SSHSAOVHNPHJDB-OBJOEFQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R,4R)-4-((4-bromophenyl)thio)-3-(2-methoxy-2-oxoethyl)-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxylate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium acetate 、 potassium carbonate 、 三(邻甲基苯基)磷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 三环己基膦 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.58h， 生成
  参考文献：
  名称：

  Synthesis of an acromelic acid A analog-based 11C-labeled PET tracer for exploration of the site of action of acromelic acid A in allodynia induction

  摘要：

  A novel C-11-labeled PET (positron emission tomography) tracer, which was designed based on the (phenylthio) pyrrolidine derivative that can competitively block the acromelic acid A-induced allodynia, was synthesized. A protocol in which methylation by palladium-mediated coupling of the boronate derivative with [C-11]CH3I and deprotection of the protected amino acid moiety are successively performed in one-pot within 5 min was established for the synthesis of the tracer. The tracer is potentially useful as a tool to investigate the mode of action of acromelic acid A in the induction of allodynia. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.018
• 作为产物：
  描述：

  (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester 在 盐酸 、 4-二甲氨基吡啶 、 氯化亚砜 、 三丁基膦 、 水 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 51.25h， 生成 methyl (2S,3R,4R)-4-((4-bromophenyl)thio)-3-(2-methoxy-2-oxoethyl)-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of an acromelic acid A analog-based 11C-labeled PET tracer for exploration of the site of action of acromelic acid A in allodynia induction

  摘要：

  A novel C-11-labeled PET (positron emission tomography) tracer, which was designed based on the (phenylthio) pyrrolidine derivative that can competitively block the acromelic acid A-induced allodynia, was synthesized. A protocol in which methylation by palladium-mediated coupling of the boronate derivative with [C-11]CH3I and deprotection of the protected amino acid moiety are successively performed in one-pot within 5 min was established for the synthesis of the tracer. The tracer is potentially useful as a tool to investigate the mode of action of acromelic acid A in the induction of allodynia. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.018