methyl 5-(4,6-dimethylpyrimidin-2-yl)-2-methyl-4-(phenylsulfonyl)pyrrolidine-2-carboxylate | 1318792-15-2

• 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 5-(4,6-dimethylpyrimidin-2-yl)-2-methyl-4-(phenylsulfonyl)pyrrolidine-2-carboxylate
• 英文别名: methyl (2S,4R,5S)-4-(benzenesulfonyl)-5-(4,6-dimethylpyrimidin-2-yl)-2-methylpyrrolidine-2-carboxylate
• CAS: 1318792-15-2
• 化学式: C₁₉H₂₃N₃O₄S
• 分子量: 389.475
• InChiKey: SHFKRTUVSWMASD-MDZRGWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,6-二甲基-2-嘧啶甲醛 、 苯基乙烯基砜 、 D-丙氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以28%的产率得到methyl 5-(4,6-dimethylpyrimidin-2-yl)-2-methyl-4-(phenylsulfonyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  XY–ZH compounds as potential 1,3-dipoles. Part 65: atom economic cascade synthesis of highly functionalized pyrimidinylpyrrolidines

  摘要：

  The results of the reaction of aminomethyl heterocycles and 4,6-dimethyl-2-formylpyrimidine and of activated secondary amines with different aryl/heteroaryl or aliphatic aldehydes and N-methylmaleimide or maleimide are described. In the former case the reactions gave single diastereomers via endo-transition states whilst the latter gave a mixture of diastereomers, which are believed to arise from anti-dipoles via endo/exo transition states. The stereochemistry of the cycloadducts was determined by (1)H NMR and confirmed by X-ray crystallography. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.074