1-(piperidinomethyl)-1H-1,2,3-benzotriazole | 15622-20-5

• 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: 1-(piperidinomethyl)-1H-1,2,3-benzotriazole
• 英文别名: 1-piperidin-1-ylmethyl-1H-benzotriazole；1-piperidinomethyl-1H-benzotriazole；1-Piperidinomethyl-1H-benzotriazol；1-(Piperidin-1-ylmethyl)-1H-1,2,3-benzotriazole；1-(piperidin-1-ylmethyl)benzotriazole
• CAS: 15622-20-5
• 化学式: C₁₂H₁₆N₄
• mdl: MFCD00187678
• 分子量: 216.286
• InChiKey: MPBMIGLZRPKNKA-UHFFFAOYSA-N

物化性质

• 熔点：
  92.5-93.5 °C
• 沸点：
  365.7±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-(piperidinomethyl)-1H-1,2,3-benzotriazole 、 2-溴丁烷 在 碘 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以62%的产率得到1-(2-methylbutyl)piperidine
  参考文献：
  名称：

  Katritzky, Alan R.; Parris, Roslyn L.; Ignatchenko, Elena S., Advanced Synthesis and Catalysis, 1996, vol. 338, # 3, p. 220 - 230

  摘要：

  DOI：
• 作为产物：
  描述：

  哌啶 、 T406石油添加剂 、 聚合甲醛 在 水 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 1-(piperidinomethyl)-1H-1,2,3-benzotriazole
  参考文献：
  名称：

  Aminoalkylbenzotriazoles: reagents for the aminoalkylation of electron rich heterocycles

  摘要：

  Secondary and tertiary aminoalkylbenzotriazoles react with pyrrole, indole, their N-methyl analogs and with 2-methylfuran under mild reaction conditions in the presence of a Lewis acid to afford selectively the corresponding secondary or tertiary amines.

  DOI：

  10.1016/s0040-4020(01)81590-8

文献信息

• Benzotriazole-assisted synthesis of novel mannich bases from ketones and diverse aldehydes
  作者：Alan R. Katritzky、Philip A. Harris

  DOI：10.1016/s0040-4020(01)81378-8

  日期：1990.1

  β-amino ketones are prepared in moderate to good yields by the reaction of the lithium enolates of cyclohexanone, acetophenone, α-tetralone and camphor with the readily available adducts from an aldehyde or ketone, an amine and benzotriazole. Some diastereoselectivity is observed when the benzotriazole adduct is derived from benzaldehyde.

  通过环己酮，苯乙酮，α-四氢萘酮和樟脑的烯醇锂与醛或酮，胺和苯并三唑的易得加合物的反应，可以以中等至良好的产率制备各种β-氨基酮。当苯并三唑加合物衍生自苯甲醛时，观察到一些非对映选择性。
• 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。
• First tandem nucleophilic addition–electrophilic amination reaction of Eschenmoser’s salts: synthesis of cyclic and spiro-fused hydrazonium salts
  作者：Jarosław Sączewski、Maria Gdaniec

  DOI：10.1016/j.tetlet.2007.08.127

  日期：2007.10

  A series of cyclic and spiro-fused hydrazonium salts was prepared by tandem nucleophilic addition–electrophilic amination reactions. The method presented makes use of Eschenmoser’s salt or benzotriazole aminals and 2-hydroxylamino-4,5-dihydroimidazolium-O-sulfonate. The products structures were determined by X-ray analysis.

  通过串联亲核加成-亲电子胺化反应制备了一系列环状和螺稠合的azo盐。提出的方法利用了埃舍莫瑟尔盐或苯并三唑缩醛胺和2-羟基氨基-4,5-二氢咪唑鎓-O-磺酸盐。通过X射线分析确定产物结构。
• 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。