N-ethyl-N-<(benzotriazol-1-yl)methyl>aniline | 147676-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: N-ethyl-N-<(benzotriazol-1-yl)methyl>aniline
• 英文别名: N-Ethyl-N-phenyl-1H-benzotriazole-1-methanamine；N-(1H-1,2,3-Benzotriazol-1-ylmethyl)-N-ethylaniline；N-(benzotriazol-1-ylmethyl)-N-ethylaniline
• CAS: 147676-24-2
• 化学式: C₁₅H₁₆N₄
• 分子量: 252.319
• InChiKey: NJLLRMIZEVHVFY-UHFFFAOYSA-N

物化性质

• 沸点：
  426.7±28.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  N-ethyl-N-<(benzotriazol-1-yl)methyl>aniline 以 二氧六环-d8 为溶剂， 生成 N-ethyl-N-<(benzotriazol-2-yl)methyl>aniline
  参考文献：
  名称：

  Kinetics, catalysis, and mechanism of isomerization ofN-[(benzotriazol-1-yl)methyl]anilines into the benzotriazol-2-yl derivatives

  摘要：

  AbstractThe 1H NMR technique was applied for the measurement of the isomerization rates of N‐ethyl‐N‐[(benzotriazol‐1‐yl)methyl]aniline (4) and 4‐butyl‐N‐[(benzotriazol‐1‐yl)methyl]aniline (7) to the corresponding benzotriazol‐2‐yl isomers in dioxane‐d8 at 35°C. The rate constants obtained for pure dioxane‐d8 were 1.62 and 0.28 h−1 for 4 and 7, respectively. For both compounds, addition to acetic acid to the dioxane solutions accelerated the isomerizations whereas addition of triethylamine retarded it strongly. Addition of water slowed the isomerization of 4 but accelerated that of 7: the different effects operating in the two cases are discussed and rationalized. © 1995 John Wiley & Sons, Inc.

  DOI：

  10.1002/kin.550270406
• 作为产物：
  描述：

  N-ethyl-N-<(benzotriazol-2-yl)methyl>aniline 以 二氧六环-d8 为溶剂， 生成 N-ethyl-N-<(benzotriazol-1-yl)methyl>aniline
  参考文献：
  名称：

  Kinetics, catalysis, and mechanism of isomerization ofN-[(benzotriazol-1-yl)methyl]anilines into the benzotriazol-2-yl derivatives

  摘要：

  AbstractThe 1H NMR technique was applied for the measurement of the isomerization rates of N‐ethyl‐N‐[(benzotriazol‐1‐yl)methyl]aniline (4) and 4‐butyl‐N‐[(benzotriazol‐1‐yl)methyl]aniline (7) to the corresponding benzotriazol‐2‐yl isomers in dioxane‐d8 at 35°C. The rate constants obtained for pure dioxane‐d8 were 1.62 and 0.28 h−1 for 4 and 7, respectively. For both compounds, addition to acetic acid to the dioxane solutions accelerated the isomerizations whereas addition of triethylamine retarded it strongly. Addition of water slowed the isomerization of 4 but accelerated that of 7: the different effects operating in the two cases are discussed and rationalized. © 1995 John Wiley & Sons, Inc.

  DOI：

  10.1002/kin.550270406

文献信息

• A Convenient Synthesis of<i>N</i>-(α-Alkoxyalkyl)- and<i>N</i>-[α-(Alkylthio)alkyl]amines
  作者：Alan R. Katritzky、Wei-Qiang Fan、Qiu-He Long

  DOI：10.1055/s-1993-25837

  日期：——

  Aminoalkylation of alcohols and of thiols by N-[1-(benzotriazol-1-yl)alkyl]amines under mild conditions give N-(α-alkoxyalkyl)amines 2 and N-[α-(alkylthio)alkyl]amines 3, respectively, in good yields.

  在温和条件下，N-[1-(苯并三唑-1-基)烷基]胺对醇和硫醇进行氨烷基化，得到 N-(α-烷氧基烷基)胺 2 和 N-[α-(烷硫基)烷基]胺 3 ，分别获得良好的收益。
• 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.
• 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.
• Lithium tetrafluoroborate-assisted reactions of N-(.alpha.-aminoalkyl)benzotriazoles with olefins and 1,3-dienes. New syntheses of 1,2,5,6-tetrahydropyridinium salts, 1,2,3,4-tetrahydroquinolines, and some related heterocyclic systems
  作者：Alan R. Katritzky、Mikhail F. Gordeev

  DOI：10.1021/jo00067a043

  日期：1993.7

  Lithium tetrafluoroborate efficiently assists the ionization of N-(alpha-aminoalkyl)benzotriazoles in tetrahydrofuran solution to generate reactive iminium intermediates, which can be trapped with electron-rich olefins and with 1,3-dienes. Hetero Diels-Alder cycloadditions of N-(alpha-dialkylami-noalkyl)benzotriazoles and lithium tetrafluoroborate with 1,3-dienes thus gave 1,2,5,6-tetrahydropyridinium salts, while reactions of N-[alpha-(arylamino)alkyl]benzotriazoles with olefins and 1,3-dienes afforded substituted 1,2,3,4-tetrahydroquinolines, as well as examples of the new heterocyclic systems indeno[2,1-c]quinoline and pyrido[3,2,1-kl]-1,4-phenothiazine.