(2R,4S)-dimethyl 6-methoxy-4-((4-methoxyphenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinoline-2,4-dicarboxylate | 1437308-04-7

• 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: (2R,4S)-dimethyl 6-methoxy-4-((4-methoxyphenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinoline-2,4-dicarboxylate
• 英文别名: dimethyl (2R,4S)-6-methoxy-4-(4-methoxyanilino)-2-methyl-1,3-dihydroquinoline-2,4-dicarboxylate
• CAS: 1437308-04-7
• 化学式: C₂₂H₂₆N₂O₆
• 分子量: 414.458
• InChiKey: ITCGPHSZDXPSTA-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,4S)-dimethyl 6-methoxy-4-((4-methoxyphenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinoline-2,4-dicarboxylate 在 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 32.0h， 以94%的产率得到
  参考文献：
  名称：

  A Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines: Quaternary Stereogenic Center Inversion and Functionalization

  摘要：

  Tetrahydroquinolines containing two quaternary stereogenic centers were synthesized with excellent ee and dr via a four-component cyclization reaction catalyzed by a chiral phosphoric acid. High chemoselectivity was achieved by differentiating anilines with similar reactivities to yield diverse hybrid products. The chirality of the quaternary C4 atom of the 4-aminotetrahydroquinoline products was found to undergo highly stereoselective inversion, enabling facile functionalization using a wide range of nucleophiles (C, O, N, and S).

  DOI：

  10.1021/ja4040945
• 作为产物：
  描述：

  丙酮酸甲酯 、 甲氧苯胺 在 C₄₈H₃₇O₄P 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以65%的产率得到(2R,4S)-dimethyl 6-methoxy-4-((4-methoxyphenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinoline-2,4-dicarboxylate
  参考文献：
  名称：

  A Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines: Quaternary Stereogenic Center Inversion and Functionalization

  摘要：

  Tetrahydroquinolines containing two quaternary stereogenic centers were synthesized with excellent ee and dr via a four-component cyclization reaction catalyzed by a chiral phosphoric acid. High chemoselectivity was achieved by differentiating anilines with similar reactivities to yield diverse hybrid products. The chirality of the quaternary C4 atom of the 4-aminotetrahydroquinoline products was found to undergo highly stereoselective inversion, enabling facile functionalization using a wide range of nucleophiles (C, O, N, and S).

  DOI：

  10.1021/ja4040945