1-(1H-Pyrrol-1-ylmethyl)-1H-1,2,3-benzotriazole | 124337-35-5

• 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-(1H-Pyrrol-1-ylmethyl)-1H-1,2,3-benzotriazole
• 英文别名: 1-(pyrrol-1-ylmethyl)benzotriazole
• CAS: 124337-35-5
• 化学式: C₁₁H₁₀N₄
• 分子量: 198.227
• InChiKey: PSSVYPCDGXKGRM-UHFFFAOYSA-N

物化性质

• 沸点：
  389.3±25.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1H-Pyrrol-1-ylmethyl)-1H-1,2,3-benzotriazole 在 氢氧化钾 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 N-(1-cyclohexen-1-yl)-1H-pyrrole
  参考文献：
  名称：

  Synthesis of N-Cycloalkenylazoles

  摘要：

  N-(1-Cycloalkenyl)pyrroles 3a,b, -pyrazoles 6a,b, and -imidazoles 9a,b were synthesized via elimination of benzotriazole or 5-phenyltetrazole from the corresponding 1-[1-(heterocycyl)cycloalkyl]-benzotriazoles 2, 5, and 8 or 1-[1-(heterocycyl)cyclohexyl] 5-phenyltetrazole (12 and 14). Intermediates 2, 5, 8, 12 and 14 were obtained by cyclizations of dihaloalkanes with N-(benzotriazol-1-ylmethyl)heterocycles, 1-imidazol-1-ylmethyl-5-plienyltetrazole (11), or 1-pyrazol-1-ylmethyl-5-phenyltetrazole (13) in the presence of n-BuLi.

  DOI：

  10.1021/jo020336m
• 作为产物：
  描述：

  吡咯 、 1-(氯甲基)-1H-苯并三唑 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到1-(1H-Pyrrol-1-ylmethyl)-1H-1,2,3-benzotriazole
  参考文献：
  名称：

  5-氮杂富烯离子与烯胺的反应：吡咯嗪的新方法

  摘要：

  的合成Ñ，Ñ二甲基ñ - [（吡咯烷-1-基）甲基]苯胺氯化物（14）和相应的p -toluidinium盐15进行说明。这些盐，当溶解于极性溶剂中时，显示与1-（氯甲基）吡咯（17）处于平衡状态，因此潜在地与5-氮杂富烯离子（2）处于平衡状态。因此，它们在非常温和的条件下（MeCN，60°）与烯胺反应，以可接受的收率（40–50°）得到吡咯嗪衍生物。根据最初的曼尼希型反应，然后立即进行无环化，使该过程合理化。

  DOI：

  10.1002/hlca.19910740824

文献信息

• 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。
• A new route to N-substituted heterocycles
  作者：Alan R. Katritzky、Hengyuan Lang、Xiangfu Lan

  DOI：10.1016/s0040-4020(01)80382-3

  日期：1993.4

  -carbazole, and -benzimidazole, and analogs substituted in the methylene group are converted by lithium aluminum hydride, or by Grignard reagents, or in two cases by organozinc reagents, into the N-substituted heterocycles in good yields.

  N-（苯并三唑-1-基甲基）-吲哚，吡咯，-咔唑和-苯并咪唑以及在亚甲基中取代的类似物通过氢化铝锂，格氏试剂或两种情况下的有机锌试剂转化为N-取代的杂环具有良好的收率。
• Katritzky, Alan R.; Drewniak-Deyrup, Malgorzata; Lan, Xiangfu, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 829 - 836
  作者：Katritzky, Alan R.、Drewniak-Deyrup, Malgorzata、Lan, Xiangfu、Brunner, Frederic

  DOI：——

  日期：——
• A Novel Transformation of Esters to Alkynes with 1-Substituted Benzotriazoles
  作者：Alan R. Katritzky、Jin Wang、Nazira Karodia、Jianqing Li

  DOI：10.1021/jo962291t

  日期：1997.6.13

  Reactions of lithio benzotriazol-1-yl derivatives 2, 11, and 25 with aromatic and aliphatic esters 3, 12, and 26 gave alpha-(benzotriazol-1-yl) ketones 4, 13, and 27, respectively, in high yields. Alternatively, alpha-(benzotriazol-1-yl) ketones 22 can be accessed by the reaction of alpha-(benzotriazol-1-yl) esters 20 with Grignard reagents. Condensation of 4, 13, 22, and 27 with (p-toluenesulfonyl)hydrazine provided p-tosylhydrazones 5, 14, 21, and 28. Treatment of hydrazones 5, 21, and 28 with n-butyllithium in diethyl ether resulted in the elimination of the tosyl group, dinitrogen, and benzotriazolyl group to afford the corresponding acetylenes 9, 23, and 29 in good yields. When alpha-(benzotriazol-1-yl) 1-alpha-phenoxy hydrazones 14 were treated with methyllithium, n-butyllithium, or phenyllithium, alkynes 18 were obtained, in which phenoxy groups were replaced by the lithium reagents.
• Katritzky, Alan R.; Wang, Junquan; Henderson, Scott A., Heterocycles, 1998, vol. 48, # 8, p. 1567 - 1574
  作者：Katritzky, Alan R.、Wang, Junquan、Henderson, Scott A.

  DOI：——

  日期：——