(Benzotriazol-1-yl-phenyl-methyl)-methyl-phenyl-amine | 142992-81-2

• 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: (Benzotriazol-1-yl-phenyl-methyl)-methyl-phenyl-amine
• 英文别名: N-[benzotriazol-1-yl(phenyl)methyl]-N-methylaniline
• CAS: 142992-81-2
• 化学式: C₂₀H₁₈N₄
• 分子量: 314.39
• InChiKey: XFMLFRWWOAIRIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (Benzotriazol-1-yl-phenyl-methyl)-methyl-phenyl-amine 以72%的产率得到
  参考文献：
  名称：

  Huang Ke-Xin, Du Shao-Bin, Fan Wei-Qiang, Youji huaxue (Org. Chem), 13 (1993) N 5, S 513-517

  摘要：

  DOI：
• 作为产物：
  描述：

  T406石油添加剂 、 苯甲醛 、 N-甲基苯胺 以64%的产率得到
  参考文献：
  名称：

  Huang Ke-Xin, Du Shao-Bin, Fan Wei-Qiang, Youji huaxue (Org. Chem), 13 (1993) N 5, S 513-517

  摘要：

  DOI：

文献信息

• <i>N</i>-(α-Aminoalkyl)benzotriazoles:  Novel “Nonstabilized” α-Aminocarbanion Synthons
  作者：Alan R. Katritzky、Ming Qi、Daming Feng、Daniel A. Nichols

  DOI：10.1021/jo962247d

  日期：1997.6.13

  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.
• A New Method of Synthesis for Propargylic Amines and Ethers via Benzotriazole Derivatives Using Sodium Dialkynyldiethylaluminates
  作者：Jin Hee Ahn、Meyoung Ju Joung、Nung Min Yoon、Daniela C. Oniciu、Alan R. Katritzky

  DOI：10.1021/jo9814750

  日期：1999.1.1

  1-(alpha-Aminoalkyl)benzotriazoles react with sodium dialkynyldiethylaluminates to give propargylic amines in excellent yields, including unsubstituted N,N-dialkyl propargylamines, which are difficult to obtain from Lithium acetylide. The reaction of alpha-benzotriazolyl alkyl ethers and sodium dialkynyldiethylaluminate in the presence of zinc iodide also gives propargylic ethers in excellent yields. Unsubstituted propargyl ethers are prepared via the desilylation of trimethylsilylpropargyl ethers.
• 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.
• Huang Ke-Xin, Du Shao-Bin, Fan Wei-Qiang, Youji huaxue (Org. Chem), 13 (1993) N 5, S 513-517
  作者：Huang Ke-Xin, Du Shao-Bin, Fan Wei-Qiang

  DOI：——

  日期：——