benzotriazol-1-ylmethyl-diphenyl-amine | 15497-48-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: benzotriazol-1-ylmethyl-diphenyl-amine
• 英文别名: n-(1h-Benzotriazol-1-ylmethyl)-n-phenylaniline；N-(benzotriazol-1-ylmethyl)-N-phenylaniline
• CAS: 15497-48-0
• 化学式: C₁₉H₁₆N₄
• 分子量: 300.363
• InChiKey: JHTBDSXEVYRGNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  3-甲基-2-丁酮 、 benzotriazol-1-ylmethyl-diphenyl-amine 在 samarium diiodide 、 benzotriazol-2-ylmethyl-diphenyl-amine 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到1-Diphenylamino-2,3-dimethyl-butan-2-ol
  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
• 作为产物：
  描述：

  1H-苯并三唑-1-甲醇 、 二苯胺 生成 benzotriazol-1-ylmethyl-diphenyl-amine
  参考文献：
  名称：

  Water-tolerant unstabilized carbanion equivalents: Bismuth(III) chloride-aluminum promoted alkylations of immonium cations to amines in aqueous Media

  摘要：

  In the presence of bismuth(III) chloride-metallic aluminum, alkyl as well as allyl halides react with N-(alkylamino)benzotriazoles at 20-degrees-C in THF-water to give the corresponding homoalkylated amines in high yields.

  DOI：

  10.1016/s0040-4039(00)92139-7

文献信息

• Lewis acid assisted reactions of<i>N</i>-(α- aminoalkyl)benzotriazoles and unactivated alkenes for the facile synthesis of 4-, 2,4-, and 3,4-substituted 1,2,3,4-tetrahydroquinolines
  作者：Alan R. Katritzky、Daniel A. Nichols、Ming Qi、Baozhen Yang

  DOI：10.1002/jhet.5570340428

  日期：1997.7

  A range of substituted tetrahydroquinolines have been synthesized from benzotriazole derivatives and unactivated alkenes in the presence of a Lewis acid. These reactions utilize readily available starting materials and mild reaction conditions, and give high yields. The reaction mechanisms are discussed.

  在路易斯酸的存在下，由苯并三唑衍生物和未活化的烯烃合成了一系列取代的四氢喹啉。这些反应利用容易获得的原料和温和的反应条件，并获得高收率。讨论了反应机理。
• Reactions of<i>N</i>-aryl-1<i>H</i>-benzotriazolyl-1-methanamines with allyl trimethylsilanes. A facile route to trialkylsilane tetrahydroquinolines
  作者：Alan R. Katritzky、Xilin Cui、Qiuhe Long

  DOI：10.1002/jhet.5570360207

  日期：1999.3

  N-Aryl-1H-benzotriazolyl-1-methanamines 1, easily accessible from the condensation of anilines with formaldehyde and benzotriazole, undergo Lewis acid assisted reactions with allyl trimethylsilanes to give 4-(trimethylsilyl)methyl-1,2,3,4-tetrahydroquinolines 2 in good to high yields.

  N-芳基-1 H-苯并三唑基-1-甲胺1易于从苯胺与甲醛和苯并三唑的缩合反应中进行，与路易斯烯酸三甲基硅烷进行路易斯酸辅助反应，得到4-（三甲基甲硅烷基）甲基-1,2,3,4 -四氢喹啉2高至高收率。
• SYNTHESIS AND EVALUATION OF HEPATOPROTECTIVE ACTIVITY OF SOME NEW MANNICH BASES BEARING BENZTRIAZOLE MOIETY
  作者：AIYALU RAJASEKARAN、MUTHUSAMY PERIYASAMY

  DOI：10.4067/s0717-97072010000300021

  日期：——

  A series of benztriazoles bearing Mannich bases (2 -10) were synthesized from benztriazole by aminomethylation with formaldehyde and various substituted secondary amines. Titled compounds were synthesized by Mannich reaction and they were characterized by IR and 1HNMR spectroscopy. All these Mannich bases were screened for hepatoprotective activity on carbon tetrachloride induced liver damage in rats

  由苯并三唑与甲醛和各种取代的仲胺进行氨甲基化反应，由苯并三唑合成了一系列带有曼尼希碱的苯并三唑（2 -10）。通过Mannich反应合成标题化合物，并通过IR和1HNMR光谱对其进行表征。筛选所有这些曼尼希碱对四氯化碳诱导的大鼠肝损伤的肝保护活性。只有化合物4（250 mg / kg）可以有效保护动物免受四氯化碳诱导的肝毒性。化合物4 N-吗啉基甲基苯并三唑显示出与标准药物水飞蓟素相当的显着活性。
• Benzotriazole stabilizers for polyols and polyurethane foam
  申请人：R.T. VANDERBILT COMPANY, Inc.

  公开号：EP0839861A2

  公开（公告）日：1998-05-06

  Polyether and polyester poloyols and polyurethane foams are stabilized by including therein stabilizers selected from (1) diphenylaminomethylbenzotriazole substituted by alkyl or phenylalkyl groups or (2) synergistic compositions consisting of (a) benzotriazole or alkylbenzotriazole and (b) secondary aromatic amine substituted by alkyl or phenylalkyl groups wherein the benzotriazole and amine is present in critical ratios. Furthermore, a method is disclosed for preparation of polyurethane foams from polyols and polyisocyanate that have reduced discoloration due to scorch by adding diphenylamino methylbenzotriazole or compositions of benzotriazole and secondary aromatic amine as scorch inhibitors to the polyol, foaming the polyol and curing.

  聚醚和聚酯多元醇以及聚氨酯泡沫的稳定剂选自 (1) 被烷基或苯基烷基取代的二苯基氨基甲基苯并三唑或 (2) 由 (a) 苯并三唑或烷基苯并三唑和 (b) 被烷基或苯基烷基取代的仲芳香族胺组成的增效组合物，其中苯并三唑和胺以临界比例存在。 此外，还公开了一种用多元醇和多异氰酸酯制备聚氨酯泡沫的方法，通过向多元醇中添加二苯基氨基甲基苯并三唑或苯并三唑和仲芳香族胺的组合物作为焦烧抑制剂，使多元醇发泡并固化，从而减少焦烧引起的变色。
• 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.