1-methyl-4-(benzotriazol-N-yl)-1,2,3,4-tetrahydroquinoline | 146041-91-0

• 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-methyl-4-(benzotriazol-N-yl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 4-(Benzotriazol-1-yl)-1-methyl-1,2,3,4-tetrahydroquinoline；4-(1H-1,2,3-Benzotriazol-1-yl)-1-methyl-1,2,3,4-tetrahydroquinoline；4-(benzotriazol-1-yl)-1-methyl-3,4-dihydro-2H-quinoline
• CAS: 146041-91-0
• 化学式: C₁₆H₁₆N₄
• 分子量: 264.33
• InChiKey: NVFNHAIQAMNQQW-UHFFFAOYSA-N

物化性质

• 沸点：
  454.9±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  癸醇 、 1-methyl-4-(benzotriazol-N-yl)-1,2,3,4-tetrahydroquinoline 在 sodium hydride 作用下， 反应 16.0h， 以79%的产率得到4-(Decyloxy)-1-methyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  A Versatile Method for the Preparation of Substituted 1,2,3,4-Tetrahydroquinolines

  摘要：

  N-Alkyl-N-aryl-1H-benzotriazole-1-methanamines 1 react with acetaldehyde to give 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 11 in good yields along with minor amounts of diamines 12. Reactions of 1 with higher enolizable aldehydes R(1)CH(2)CHO lead to 4-(benzotriazol-1-yl)tetrahydroquinolines with an R(1) substituent at C-3 (17, 18). Condensation of N-methylaniline with two molecules of aldehyde RCH(2)CHO and one molecule of benzotriazole produces 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 34 bearing an R substituent at C-3 and RCH(2) on C-2. In all of these products, the benzotriazol-1-yl moiety can be replaced by a hydrogen atom (by reduction with lithium aluminum hydride) or by an alkyl or aryl group (by reaction with a Grignard reagent). Treatment of 11 with sodium alkoxides leads to 4-alkoxy-1,2,3,4-tetrahydroquinolines 10. Elimination of a molecule of nitrogen from the benzotriazole system of 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 17, 18, and 35 by sodium hydride produces the corresponding 4-(phenylamino)-1,2-dihydroquinolines 26 (R(1) = alkyl) or 4-(phenylimino)-1,2,3,4-tetrahydroquinolines 27 and 38 (R = Ph), depending on the nature of the substituents at C-3 and the workup conditions.

  DOI：

  10.1021/jo00128a041
• 作为产物：
  描述：

  N-甲基-N-苯基苯并三唑甲胺 、 乙烯基乙醚 以32%的产率得到1-methyl-4-(benzotriazol-N-yl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Additions of 1-(aminomethyl)benzotriazoles to enamines, enamides, and vinyl ethers: novel routes to 1,3-diamines and tetrahydroquinolines

  摘要：

  New methods for the synthesis of 1,3-diamines and of 4-substituted tetrahydroquinolines are described in which the key step is the addition of the condensation products derived from amines, aldehydes, and benzotriazole to enamines, enamides, and vinyl ethers.

  DOI：

  10.1021/jo00056a006

文献信息

• Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with .alpha.,.beta.-Unsaturated Ethers. A Novel Route to 1,4- and 1,3-Disubstituted 1,2,3,4-Tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00113a043

  日期：1995.4

  N-Alkyl-N-aryl-1H-benzotriazole-1-methanamines 3, easily accessible from the condensation of anilines with formaldehyde and benzotriazole, undergo acid-catalyzed reactions with ethyl vinyl ether to give 1-allkyl-4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 10 and their benzotriazol-2-yl isomers 11. The reaction mechanism involves formation of 1-alkyl-4-ethoxy-1,2,3,4-tetrahydroquinolines 8 as isolable intermediates, followed by substitution of the ethoxy group in 8 with benzotriazole to produce 10 and 11, Treatment with Grignard reagents in toluene converts compounds 10 and 11 in good yield to 4-alkyl- or 4-aryltetrahydroquinolines 12. 2,3-Dihydrofuran and 3,4-dihydro-2H-pyran undergo similar reaction sequences giving tetrahydroquinolines additionally substituted by 3-(beta-hydroxyethyl) and 3-(gamma-hydroxypropyl) groups, respectively. The stereochemistry of 1,3,4-trisubstituted 1,2,3,4-tetrahydroquinolines is assigned on the basis of NOE methodology. An unusual reduction of the benzotriazolyl moiety to a phenylamino group is observed in the case of product 43 obtained from the reaction of 10-(benzotriazol-1-ylmethyl)-4H-phenothiazine with ethyl vinyl ether.
• A Versatile Method for the Preparation of Substituted 1,2,3,4-Tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00128a041

  日期：1995.11

  N-Alkyl-N-aryl-1H-benzotriazole-1-methanamines 1 react with acetaldehyde to give 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 11 in good yields along with minor amounts of diamines 12. Reactions of 1 with higher enolizable aldehydes R(1)CH(2)CHO lead to 4-(benzotriazol-1-yl)tetrahydroquinolines with an R(1) substituent at C-3 (17, 18). Condensation of N-methylaniline with two molecules of aldehyde RCH(2)CHO and one molecule of benzotriazole produces 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 34 bearing an R substituent at C-3 and RCH(2) on C-2. In all of these products, the benzotriazol-1-yl moiety can be replaced by a hydrogen atom (by reduction with lithium aluminum hydride) or by an alkyl or aryl group (by reaction with a Grignard reagent). Treatment of 11 with sodium alkoxides leads to 4-alkoxy-1,2,3,4-tetrahydroquinolines 10. Elimination of a molecule of nitrogen from the benzotriazole system of 4-(benzotriazol-1-yl)-1,2,3,4-tetrahydroquinolines 17, 18, and 35 by sodium hydride produces the corresponding 4-(phenylamino)-1,2-dihydroquinolines 26 (R(1) = alkyl) or 4-(phenylimino)-1,2,3,4-tetrahydroquinolines 27 and 38 (R = Ph), depending on the nature of the substituents at C-3 and the workup conditions.
• Additions of 1-(aminomethyl)benzotriazoles to enamines, enamides, and vinyl ethers: novel routes to 1,3-diamines and tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00056a006

  日期：1993.2

  New methods for the synthesis of 1,3-diamines and of 4-substituted tetrahydroquinolines are described in which the key step is the addition of the condensation products derived from amines, aldehydes, and benzotriazole to enamines, enamides, and vinyl ethers.