methyl (-)-(1S,3S,3aR,6aS,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate | 647833-68-9

• 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 (-)-(1S,3S,3aR,6aS,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate
• CAS: 647833-68-9
• 化学式: C₂₂H₂₃NO₄S
• 分子量: 397.495
• InChiKey: KDIRVWZQWIRLOO-NHQSICLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (-)-(1S,3S,3aR,6aS,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate 在 镍 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以84%的产率得到methyl (+)-(1S,3R,3aS,6aR)-4-oxo-3-phenyloctahydrocyclopenta[c]pyrrole-1-carboxylate
  参考文献：
  名称：

  Formal Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides to (S)-2-p-Tolylsulfinyl-2-cyclopentenone

  摘要：

  Azomethine ylides, derived from iminoesters 1 and DBU in the presence of silver salts, react with (S)-2-p-tolylsulfinyl-2-cyclopentenone 2 in a completely regio- and endoselective manner but with a low facial selectivity, affording a mixture of two cycloadducts 3 and 4. When the ylides were prepared with LHMDS, only one diastereoisomer 3 was obtained in an almost quantitative yield. A nucleophilic addition/ring closure process easily accounts for the stereochemical results. Compounds 3 were transformed into optically pure 4-oxocyclopenta[c]dihydropyrroles and tetrahydropyrroles by elimination of the sulfinyl group.

  DOI：

  10.1021/jo035369w
• 作为产物：
  描述：

  Methyl (E)-N-benzylideneglycinate 、 (S)-(+)-2-(p-tolylsulfinyl)-2-cyclopentenone 在 silver(I) acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.37h， 以38%的产率得到methyl (-)-(1S,3S,3aR,6aS,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate
  参考文献：
  名称：

  Formal Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides to (S)-2-p-Tolylsulfinyl-2-cyclopentenone

  摘要：

  Azomethine ylides, derived from iminoesters 1 and DBU in the presence of silver salts, react with (S)-2-p-tolylsulfinyl-2-cyclopentenone 2 in a completely regio- and endoselective manner but with a low facial selectivity, affording a mixture of two cycloadducts 3 and 4. When the ylides were prepared with LHMDS, only one diastereoisomer 3 was obtained in an almost quantitative yield. A nucleophilic addition/ring closure process easily accounts for the stereochemical results. Compounds 3 were transformed into optically pure 4-oxocyclopenta[c]dihydropyrroles and tetrahydropyrroles by elimination of the sulfinyl group.

  DOI：

  10.1021/jo035369w