methyl (-)-(1R,3R,3aS,6aR,S_S)-3-(2-naphthyl)-4-oxo-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate | 647833-74-7

• 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 (-)-(1R,3R,3aS,6aR,S_S)-3-(2-naphthyl)-4-oxo-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate
• 英文别名: methyl (1R,3R,3aS,6aR)-3a-[(S)-(4-methylphenyl)sulfinyl]-3-naphthalen-2-yl-4-oxo-1,2,3,5,6,6a-hexahydrocyclopenta[c]pyrrole-1-carboxylate
• CAS: 647833-74-7
• 化学式: C₂₆H₂₅NO₄S
• 分子量: 447.555
• InChiKey: MHGUSXIUHLUYTB-WXNXFRQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (-)-(1R,3R,3aS,6aR,S_S)-3-(2-naphthyl)-4-oxo-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate 以 甲苯 为溶剂， 反应 2.5h， 以96%的产率得到methyl 3-(2-naphthyl)-4-oxo-2,4,5,6-tetrahydrocyclopenta[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-[(2-naphthyl)methylene]glycinate 、 (S)-(+)-2-(p-tolylsulfinyl)-2-cyclopentenone 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 以93%的产率得到methyl (-)-(1R,3R,3aS,6aR,S_S)-3-(2-naphthyl)-4-oxo-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