1-Ethyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline | 167288-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-Ethyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 1-(1-ethyl-3,4-dihydro-2H-quinolin-4-yl)pyrrolidin-2-one
• CAS: 167288-18-8
• 化学式: C₁₅H₂₀N₂O
• 分子量: 244.337
• InChiKey: UBJUFXUGNWMAHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Ethyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1-Ethyl-4-(pyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with N-Vinylamides and N-Vinylcarbazole. A Convenient Synthesis of 4-(Dialkylamino)tetrahydroquinolines

  摘要：

  Reactions of N-alkyl-N-phenyl-1H-benzotriazole-1-methanamines 1 with N-vinyl-2-pyrrolidinone and with N-vinyl-N-methylacetamide give 4-(2-pyrrolidinon-1-yl)- and 4-(N-methylacetamido-N-yl)-1,2,3 ,4-tetrahydroquinolines (5 and 32), respectively. In a reaction with N-vinyl-2-pyrrolidinone, alpha-alkyl (11) and alpha-aryl(18) derivatives of 1 stereoselectively give cis-2,4-disubstituted tetrahydroquinolines 16 and 21, respectively. The 2-pyrrolidinon-1-yl and acetamido-N-yl substituents in the products are reduced with lithium aluminum hydride to the corresponding amino groups. Similar reactions of N-phenyl-1H-benzotriazole-1-methanamines 1 with 9-vinylcarbazole (40) lead to the corresponding 4-(carbazol-9-yl)-1,2,3,4-tetrahydroquinolines (41 and 42) and/or analogous 4-(benzotriazol-1-yl) or 4-(benzotriazol-2-yl) derivatives (37, 38, 43, and 44), depending on the nature of the starting material and the reaction conditions. By commencing with aniline derivatives in which the nitrogen atom is built into a heterocyclic system, this method allows for the addition of a another ring to the system, as exemplified by the conversion of phenothiazine into 46 and [3,1]benzoxazine into 49, 52, and 53.

  DOI：

  10.1021/jo00118a014
• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 N-(ethoxymethyl)-N-ethylaniline 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到1-Ethyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Stereoselective Approach to the Pyrroloquinoline Core of Martinelline

  摘要：

  描述了 α-氨基腈 4 的合成，它是马丁内林的有效前体。使用阳离子氮杂二烯 6 和作为亲二烯体的 1-(苄氧基)羰基-2-吡咯啉 5 进行正式的 [4α+2β] 环缩合，一步实现了吡咯喹啉核的制备（产率 90%）。讨论了对由此获得的三环核进行氰化过程的立体化学结果。

  DOI：

  10.1055/s-2002-33515

文献信息

• Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with N-Vinylamides and N-Vinylcarbazole. A Convenient Synthesis of 4-(Dialkylamino)tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00118a014

  日期：1995.6

  Reactions of N-alkyl-N-phenyl-1H-benzotriazole-1-methanamines 1 with N-vinyl-2-pyrrolidinone and with N-vinyl-N-methylacetamide give 4-(2-pyrrolidinon-1-yl)- and 4-(N-methylacetamido-N-yl)-1,2,3 ,4-tetrahydroquinolines (5 and 32), respectively. In a reaction with N-vinyl-2-pyrrolidinone, alpha-alkyl (11) and alpha-aryl(18) derivatives of 1 stereoselectively give cis-2,4-disubstituted tetrahydroquinolines 16 and 21, respectively. The 2-pyrrolidinon-1-yl and acetamido-N-yl substituents in the products are reduced with lithium aluminum hydride to the corresponding amino groups. Similar reactions of N-phenyl-1H-benzotriazole-1-methanamines 1 with 9-vinylcarbazole (40) lead to the corresponding 4-(carbazol-9-yl)-1,2,3,4-tetrahydroquinolines (41 and 42) and/or analogous 4-(benzotriazol-1-yl) or 4-(benzotriazol-2-yl) derivatives (37, 38, 43, and 44), depending on the nature of the starting material and the reaction conditions. By commencing with aniline derivatives in which the nitrogen atom is built into a heterocyclic system, this method allows for the addition of a another ring to the system, as exemplified by the conversion of phenothiazine into 46 and [3,1]benzoxazine into 49, 52, and 53.
• Stereoselective Approach to the Pyrroloquinoline Core of Martinelline
  作者：Jean-Pierre Hurvois、Richard Malassene、Lourdes Sanchez-Bajo、Loic Toupet、Claude Moinet

  DOI：10.1055/s-2002-33515

  日期：——

  The synthesis of α-aminonitrile 4, a potent precursor to the martinellines is described. The preparation of the pyrroloquinoline core was realized in one step (90% yield) using a formal [4π+2π] cyclocondensation involving the cationic aza-diene 6 and the 1-(benzyloxy)carbonyl-2-pyrroline 5 as dienophile. The stereo­chemical outcome of the cyanation procedure performed on the tricyclic core thus obtained is discussed.

  描述了 α-氨基腈 4 的合成，它是马丁内林的有效前体。使用阳离子氮杂二烯 6 和作为亲二烯体的 1-(苄氧基)羰基-2-吡咯啉 5 进行正式的 [4α+2β] 环缩合，一步实现了吡咯喹啉核的制备（产率 90%）。讨论了对由此获得的三环核进行氰化过程的立体化学结果。