N,N-二甲基苯并三唑甲胺 | 57684-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: N,N-二甲基苯并三唑甲胺
• 英文名称: 1-(N,N-dimethylaminomethyl)-1,2,3-benzotriazole
• 英文别名: 1-(dimethylaminomethyl)-1H-benzotriazole；benzotriazol-1-ylmethyl-dimethyl-amine；Benzotriazol-1-ylmethyl-dimethyl-amin；1-(N,N-dimethylamino-methyl)-benzotriazole；1-dimethylaminomethylbenzotriazole；1-(benzotriazol-1-yl)-N,N-dimethylmethanamine
• CAS: 57684-30-7
• 化学式: C₉H₁₂N₄
• 分子量: 176.221
• InChiKey: QABYBLFTBSCYHR-UHFFFAOYSA-N

物化性质

• 熔点：
  98-103 °C(lit.)
• 沸点：
  296.9±23.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密封装的容器中。储存时应选择阴凉、干燥的地方。

反应信息

• 作为反应物：
  描述：

  N,N-二甲基苯并三唑甲胺 、 2,3-二甲基-1,3-丁二烯 在 lithium tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以87%的产率得到1,1,3,4-tetramethyl-1,2,5,6-tetrahydropyridinium tetraphenylborate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00067a043
• 作为产物：
  描述：

  N-<(trimethylsiloxy)methyl>dimethylamine 、 1-(三甲基硅基)苯并三氮唑 以92%的产率得到
  参考文献：
  名称：

  KALININ, A. V.;APASOV, EH. T.;IOFFE, S. L.;KOZYUKOV, V. P.;KOZYUKOV, V. P+, IZV. AN CCCP. CEP. XIM., 1985, N 6, 1447-1449

  摘要：

  DOI：

文献信息

• Addition reactions of immonium benzotriazolates to acetylenic esters
  作者：Alan R. Katritzky、Clara N. Fali、Daniela C. Oniciu

  DOI：10.1016/0040-4020(94)00998-a

  日期：1995.1

  1-Dialkylaminomethylbenzotriazoles react with ethyl propiolate and dimethyl acetylenedicarboxylate by addition of the benzotriazole anion followed by the immonium cation. The benzotriazolyl group in the products undergoes facile nucleophilic displacement.

  1-二烷基氨基甲基苯并三唑与丙酸乙酯和乙酰二羧酸二甲酯反应，先加入苯并三唑阴离子，再加入铵阳离子。产物中的苯并三唑基容易发生亲核取代。
• Syntheses of 3-(substituted)-2,4,6-triphenylverdazyls
  作者：Alan R. Katritzky、Sergei A. Belyakov、H. Dupont Durst、Ruixin Xu、Naresh S. Dalal

  DOI：10.1139/v94-235

  日期：1994.8.1

  Two series of 2,4,6-triphenylverdazyls substituted at the C(3) position of the heterocyclic ring are obtained using new convenient synthetic methodology. Thus, crown ether assisted solid–liquid phase-transfer catalysis promotes the formation of 3-n-alkyl-substituted 2,4,6-triphenylverdazyls in the reactions of 1,3,5-triphenylformazan with n-alkyl bromides. Under PTC conditions, methylation of 3-(4-nitrophenyl)-1,5-diphenylformazan with methyl iodide exclusively gives the corresponding verdazyl radical. 3-Substituted 2,4,6-triphenylverdazyls containing various di(cyclo)alkylamino moieties at the C(3) position of the verdazyl ring are prepared by the reaction of 1,3,5-triphenylformazan with the corresponding 1-[N,N-di(cyclo)alkylaminomethyl]benzotriazoles under the efficient catalysis of barium hydroxide monohydrate. Sonication of this reaction allows the yields of the verdazyls to be substantially increased. A bis-verdazyl N,N-bonded in the C(3) positions was synthesized. All the radicals obtained were characterized by microanalysis, and by UV–visible and ESR spectroscopy.

  两系列在杂环环的C(3)位置取代的2,4,6-三苯基噻唑基物质，通过新的便捷合成方法得到。因此，冠醚辅助的固液相转移催化促进了1,3,5-三苯基咪唑基与n-烷基溴化物反应中3-n-烷基取代的2,4,6-三苯基噻唑基的形成。在PTC条件下，使用碘甲烷对3-(4-硝基苯基)-1,5-二苯基咪唑基进行甲基化，仅生成相应的噻唑基自由基。在噻唑基环的C(3)位置含有各种二(环)烷基氨基基团的3-取代的2,4,6-三苯基噻唑基通过1,3,5-三苯基咪唑基与相应的1-[N,N-二(环)烷基氨基甲基]苯并三唑在氢氧化钡单水合物的高效催化下反应制备。超声处理这个反应可以显著增加噻唑基的产率。合成了在C(3)位置N,N-键合的双噻唑基。所有获得的自由基都通过微量分析、UV-可见光谱和ESR光谱进行了表征。
• A General Synthesis of 1-(Dialkylaminomethyl)indoles
  作者：Brian E. Love、Binh T. Nguyen

  DOI：10.1055/s-1998-1883

  日期：1998.10

  1-(N,N-Dialkylamino)methylindoles are prepared from the corresponding 1-(dialkylaminomethyl)benzotriazoles by treatment with indole and base. The aminoalkylation proceeds in high yield with good regioselectivity.

  1-(N,N-二烷基氨基)甲基吲哚是通过用吲哚和碱处理相应的1-(二烷基氨基甲基)苯并三唑制备的。氨基烷基化反应在高产率和良好区域选择性的条件下进行。
• A New General Method for the Synthesis of Tertiary Propargylamines (<i>N,N</i>-Dialkyl-2-alkynamines)
  作者：Alan R. Katritzky、John K. Gallos、Konstantina Yannakopoulou

  DOI：10.1055/s-1989-27136

  日期：——

  A new method has been developed for the preparation of propargylamines, compounds of pharmaceutical interest. The method employs mild conditions, affords good overall yields, and is successfully applied even in cases where other methods fail.

  一种新方法已经被开发用于制备烯丙基胺，这是一类在制药领域具有重要意义的化合物。该方法采用温和的条件，具有良好的总产率，并且在其他方法失败的情况下也能成功应用。
• Capture of benzotriazole-based Mannich electrophiles by CH-acidic compounds
  作者：Jean-Christophe M. Monbaliu、Lucas K. Beagle、Finn K. Hansen、Christian V. Stevens、Ciaran McArdle、Alan R. Katritzky

  DOI：10.1039/c3ra22826f

  日期：——

  The Mannich-type capture reaction of aminoalkylbenzotriazoles by CH acidic compounds is documented. The pKa of the benzotriazole counteranion is key to the success of such reactions, whereas the global electrophilicity of the reactive iminium moiety is secondary.

  本文记录了 CH 酸性化合物对氨基烷基苯并三唑的曼尼希式俘获反应。苯并三唑反离子的 pKa 是此类反应成功的关键，而反应亚氨基的全亲电性则是次要的。