cis-1-(2-methyl-1,2,3,4-tetrahydroquinoline-4-yl) pyrrolidin-2-one

• 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: cis-1-(2-methyl-1,2,3,4-tetrahydroquinoline-4-yl) pyrrolidin-2-one
• 英文别名: cis-1-(2-methyl-1,2,3,4-tetrahydroquinoline-4-yl)pyrrolidin-2-one；cis-1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one；cis-N-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one；1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one；cis-2-methyl-4-pyrrolidin-2-one-1,2,3,4-tetrahydroquinoline；1-[(2R,4S)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: LHFKTMHOXRRTJK-MFKMUULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-1-(2-methyl-1,2,3,4-tetrahydroquinoline-4-yl) pyrrolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到cis-2-Methyl-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 、 苯胺 在 sodium dodecyl-sulfate 作用下， 以 水 为溶剂， 反应 5.0h， 以70%的产率得到cis-1-(2-methyl-1,2,3,4-tetrahydroquinoline-4-yl) pyrrolidin-2-one
  参考文献：
  名称：

  SDS胶束促进的酸催化多米诺骨牌ABB'亚氨基Diels-Alder反应：温和而高效地合成优先的2-甲基-四氢喹啉骨架†

  摘要：

  通过酸化的多米诺骨牌ABB'亚氨基狄尔斯-阿尔德反应有效合成药理学相关的4-ami基-2-甲基-1,2,3,4-四氢喹啉（THQs）的新绿色协议 水 在......的存在下 十二烷基硫酸钠（SDS）表面​​活性剂是第一次开发。研究了SDS胶束及其不同浓度（5.0、8.2和12.0 mM）对亚氨基Diels-Alder反应活性的影响。研究发现，在pH 1.0-2.5的条件下，高于临界胶束浓度（12 mM）可获得最佳的THQ收率（70-99％）。该程序导致了一般且清洁的环境友好方案，以获得具有最高生物学意义的特权非对映特异性顺式2,4-二取代THQ分子。

  DOI：

  10.1039/c3ob40171e

文献信息

• Aqueous SDS micelle-promoted acid-catalyzed domino ABB′ imino Diels–Alder reaction: a mild and efficient synthesis of privileged 2-methyl-tetrahydroquinoline scaffolds
  作者：Diego R. Merchán Arenas、Carlos A. Martínez Bonilla、Vladimir V. Kouznetsov

  DOI：10.1039/c3ob40171e

  日期：——

  A new green protocol for the efficient synthesis of pharmacologically relevant 4-amidyl-2-methyl-1,2,3,4-tetrahydroquinolines (THQs) through the domino type ABB′ imino Diels–Alder reaction in acidified water in the presence of sodium dodecyl sulphate (SDS) surfactant was developed for the first time. The influence of the SDS micelles and their different concentrations (5.0, 8.2 and 12.0 mM) on reactivity

  通过酸化的多米诺骨牌ABB'亚氨基狄尔斯-阿尔德反应有效合成药理学相关的4-ami基-2-甲基-1,2,3,4-四氢喹啉（THQs）的新绿色协议 水 在......的存在下 十二烷基硫酸钠（SDS）表面​​活性剂是第一次开发。研究了SDS胶束及其不同浓度（5.0、8.2和12.0 mM）对亚氨基Diels-Alder反应活性的影响。研究发现，在pH 1.0-2.5的条件下，高于临界胶束浓度（12 mM）可获得最佳的THQ收率（70-99％）。该程序导致了一般且清洁的环境友好方案，以获得具有最高生物学意义的特权非对映特异性顺式2,4-二取代THQ分子。
• Efficient InCl₃/H₂O-Catalyzed One-Pot Stereoselective Synthesis of<i>cis</i>-2-Methyl-4-amido-1,2,3,4-tetrahydroquinoline Derivatives
  作者：P. Prabhakara Varma、Aswathnarayana Srinivasa、Kittappa M. Mahadevan

  DOI：10.1080/00397911003650453

  日期：2011.8

  Abstract Various cis-2-methyl-4-amido-1,2,3,4-tetrahydroquinoline derivatives were synthesized efficiently by reacting aromatic amines and N-vinyl caprolactam or N-vinyl pyrrolidone in the presence of indium trichloride in an aqueous medium in good to excellent yields. These 2,4-disubstituted tetrahydrouinolines showed cis diastereoselectivity.

  摘要 在三氯化铟存在下，在水介质中，芳香胺与 N-乙烯基己内酰胺或 N-乙烯基吡咯烷酮反应，高效合成了各种顺式-2-甲基-4-酰胺基-1,2,3,4-四氢喹啉衍生物。良好的产量。这些 2,4-二取代的四氢尿啉表现出顺式非对映选择性。
• Ce(SO₄)₂-catalysed the highly diastereoselective synthesis of tetrahydroquinolines via an imino Diels Alder ABB′ type reaction and their in vivo toxicity and imaging in zebrafish embryos
  作者：Carlos A. Martínez Bonilla、Carlos E. Puerto Galvis、Leonor Y. Vargas Méndez、Vladimir V. Kouznetsov

  DOI：10.1039/c6ra04325a

  日期：——

  below their LC50, were analyzed at 48, 72 and 96 hours post fertilization, wherein the treated embryos manifested diverse visual phenotypes, such as big yolk sacs (3b, 3h, 3j), pericaldial edemas (3a, 3i) and red blood cells in the liver region (3b, 3l), in comparison to the morphology of the control embryos, the phenotypes could be associated with specific biological targets.

  已经开发出一种有效且实用的方法，以高收率和高非对映选择性合成N-（四氢喹啉基-4）酰胺3a-1。该策略包括由铈（催化亚氨基Diels Alder反应多米诺型ABB' IV苯胺和之间）盐ñ -乙烯基酰胺用于测试它们的是四氢喹啉的12元文库的制备在体内对斑马鱼胚胎毒性。确定其LC 50值后，N-（8-甲氧基-2-甲基-四氢喹啉基-4）乙酰胺3k被确定为毒性最强的衍生物，LC 50低于95μM（24 mg L-1）。最后，在受精后48、72和96小时分析浓度低于其LC 50的诱导表型，其中处理过的胚表现出不同的视觉表型，例如大卵黄囊（ 3b， 3h， 3j），梨状皮水肿（ 3a， 3i）和肝脏区域（ 3b， 3l）中的红细胞，与对照胚胎的形态相比，其表型可能与特定的生物学靶标有关。
• Inexpensive Phthalic Acid Promoted Domino Povarov Reaction between Anilines and N-Vinylamides: An Efficient Preparation of Privileged 4-Substituted 2-Methyl-1,2,3,4-tetrahydroquinoline Scaffolds
  作者：Vladimir Kouznetsov、Diego Merchan Arenas、César Ortiz Areniz、Carlos Meléndez Gómez

  DOI：10.1055/s-0031-1289591

  日期：2011.12

  An efficient and simple synthesis of new 2-methyl-1,2,3,4-tetrahydroquinolines with C4 amide fragments based on the phthalic acid promoted domino Povarov reaction between anilines and N-vinylamides has been developed.

  基于苯胺和 N-乙烯酰胺之间在邻苯二甲酸促进下发生的多米诺波瓦洛夫反应，开发出了一种高效、简单的具有 C4 酰胺片段的新型 2-甲基-1,2,3,4-四氢喹啉的合成方法。
• Reactions of Azides with Electrophiles: New Methods for the Generation of Cationic 2-Azabutadienes. Synthesis of 1,2, 3,4-Tetrahydroquinolines and 1,2-Dihydroquinolines via a Hetero Diels-Alder Reaction
  作者：William H. Pearson、Wen-Kui Fang

  DOI：10.1002/ijch.199700007

  日期：——

  rearrangement of benzylic azides and (2) the intermolecular Schmidt reactions of azides XN3 (X = aliphatic) with benzylic carbocations derived from benzylic alcohols ArCH(R)OH. The iminium ions ArN+(X)=CHR behave as cationic 2-azabutadienes in the presence of alkenes and alkynes, producing 1,2, 3,4-tetrahydroquinolines and 1,2-dihydroquinolines by a hetero Diels–Alder reaction.

  报道了两种生成ArN +（X）= CHR（X = H或烷基，R = H或烷基）类型的亚胺离子的方法：（1）布朗斯台德酸促进的苄基叠氮化物重排和（2 ）叠氮化物XN 3（X =脂族基）与衍生自苄基醇ArCH（OH）的苄基碳阳离子的分子间Schmidt反应。亚胺离子ArN +（X）= CHR在烯烃和炔烃的存在下表现为阳离子2-氮杂丁二烯，通过杂Diels-Alder反应生成1,2，3,4-四氢喹啉和1,2-二氢喹啉。