2-(N-Methylanilinomethyl)-benzotriazol | 121238-97-9

• 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: 2-(N-Methylanilinomethyl)-benzotriazol
• 英文别名: N-benzotriazol-2-ylmethyl-N-methyl-aniline；N-(benzotriazol-2-ylmethyl)-N-methylaniline
• CAS: 121238-97-9
• 化学式: C₁₄H₁₄N₄
• 分子量: 238.292
• InChiKey: CKOYOOGAXVGBFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  2-(N-Methylanilinomethyl)-benzotriazol 、 N-甲基-N-苯基苯并三唑甲胺 、 苄基氯化镁 、 四氢呋喃 、 氯化铵 生成 N-甲基-N-(2-苯基乙基)苯胺
  参考文献：
  名称：

  KATRITZKY, ALAN R.;, RACHWAL STANISLAW;WU, JING, CAN. J. CHEM., 68,(1990) N, C. 456-463

  摘要：

  DOI：
• 作为产物：
  描述：

  T406石油添加剂 、 聚合甲醛 、 N-甲基苯胺 以 乙醚 为溶剂， 生成 2-(N-Methylanilinomethyl)-benzotriazol 、 N-甲基-N-苯基苯并三唑甲胺
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00113a043
• 作为试剂：
  描述：

  N-甲基-N-苯基苯并三唑甲胺 、 3-戊酮 在 samarium diiodide 、 2-(N-Methylanilinomethyl)-benzotriazol 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到2-ethyl-1-(N-methylanilino)-2-butanol
  参考文献：
  名称：

  N-(α-Aminoalkyl)benzotriazoles:  Novel “Nonstabilized” α-Aminocarbanion Synthons

  摘要：

  C-Benzotriazole bonds were selectively transformed to give the corresponding alpha-aminocarbanions when N-(alpha-aminoalkyl)benzotriazoles were reacted with either Li/LiBr or SmI2 in the presence of representative electrophiles. The ranges of applicability of the two reagents complement each other, and together the two protocols provide a general route from readily available crystalline starting materials to a variety of ''nonstabilized'' alpha-aminocarbanions that can be trapped in moderate to good yields.

  DOI：

  10.1021/jo962247d

文献信息

• KATRITZKY, ALAN R.;, RACHWAL STANISLAW;WU, JING, CAN. J. CHEM., 68,(1990) N, C. 456-463
  作者：KATRITZKY, ALAN R.、, RACHWAL STANISLAW、WU, JING

  DOI：——

  日期：——
• 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.