N-ethyl-N-<(benzotriazol-2-yl)methyl>aniline | 162288-45-1

• 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-2-yl)methyl>aniline
• 英文别名: N-(benzotriazol-2-ylmethyl)-N-ethylaniline
• CAS: 162288-45-1
• 化学式: C₁₅H₁₆N₄
• 分子量: 252.319
• InChiKey: ARRYOKFXUMVLSB-UHFFFAOYSA-N

物化性质

• 沸点：
  414.0±47.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  33.95
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  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
• 作为产物：
  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

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.