4-Ethoxy-1-ethyl-1,2,3,4-tetrahydroquinoline | 82769-52-6

• 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: 4-Ethoxy-1-ethyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 4-ethoxy-1-ethyl-3,4-dihydro-2H-quinoline
• CAS: 82769-52-6
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: CHPFWGXVNUEPEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-ethyl-N-(methoxymethyl)aniline 、 乙烯基乙醚 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以78%的产率得到4-Ethoxy-1-ethyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Electroorganic chemistry. 62. Reaction of iminium ion with nucleophile: a versatile synthesis of tetrahydroquinolines and julolidines

  摘要：

  DOI：

  10.1021/ja00385a033

文献信息

• 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.
• 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.
• Electroorganic chemistry. 62. Reaction of iminium ion with nucleophile: a versatile synthesis of tetrahydroquinolines and julolidines
  作者：Tatsuya Shono、Yoshihiro Matsumura、Kenji Inoue、Hiroshi Ohmizu、Shigenori Kashimura

  DOI：10.1021/ja00385a033

  日期：1982.10