1-(Thien-2-ylmethyl)-1H-1,2,3-benzotriazole | 193893-30-0

• 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-(Thien-2-ylmethyl)-1H-1,2,3-benzotriazole
• 英文别名: 1-(thiophen-2-yl)methyl-1H-benzo[d][1,2,3]triazole；1-(Thiophen-2-ylmethyl)benzotriazole
• CAS: 193893-30-0
• 化学式: C₁₁H₉N₃S
• 分子量: 215.279
• InChiKey: LAUXGHHWGRBMER-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  410.7±28.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(Thien-2-ylmethyl)-1H-1,2,3-benzotriazole 在 正丁基锂 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 77.5h， 生成 N-phenyl-2-(thiophen-2-yl)acetamide
  参考文献：
  名称：

  Efficient Syntheses of 2-Functionalized Thiophenes, Cyclopent[b]thiophenes, and Polysubstituted Benzo[b]thiophenes from 2-(Benzotriazol-1-ylmethyl)thiophenes

  摘要：

  Diverse 2-(functionalized-alkyl)- and 2-alkenylthiophenes 2a,b, 4a,b, and 6a-d are prepared via the side chain elaboration of 2-(benzotriazol-1-ylmethyl)thiophenes 3a,b, themselves readily available from the condensation of 1-(hydroxymethyl)benzotriazole with thiophenes 1a,b. Treatment of 2-(benzotriazol-1-ylmethyl)thiophenes 3b and 5gj with styrenes in the presence of zinc bromide results in formal [3 + 2] cycloaddition to give in good yields substituted cyclopent[b]thiophenes 16a/17a, 16b/17b, and 18. Lithiation and 1,4-addition to a variety of alpha,beta-unsaturated ketones and aldehydes, and subsequent acid-catalyzed intramolecular cyclization followed by debenzotriazolylation-dehydration converts 3 and 5 to a range of polysubstituted benzo[b]thiophenes 19a-d and 25a-e in moderate to excellent yields. NOE difference spectroscopy and NMR H-1-C-13 long-range correlation support structures of types 19 and 25 and exclude those of type 26, thus confirming the cyclization pathway.

  DOI：

  10.1021/jo970672g
• 作为产物：
  描述：

  2-甲基噻吩 、 T406石油添加剂 在 叔丁基过氧化氢 、 1-甲基吡啶碘化物 作用下， 以 neat (no solvent) 为溶剂， 反应 12.0h， 以36%的产率得到1-(Thien-2-ylmethyl)-1H-1,2,3-benzotriazole
  参考文献：
  名称：

  在无金属条件下，通过sp 3 C–N键的形成， 可重复利用的离子液体催化的吡咯和苄基化合物的氧化偶联†

  摘要：

  杂环的离子液体催化的直接氧化的苄基胺化的SP 3 C-H键通过分子间的SP 3 C-N键的形成用于合成Ñ烷基化无金属的条件下唑类报道首次。催化剂碘化1-丁基吡啶鎓碘可以再循环并以相似的效率重复使用至少八个循环。

  DOI：

  10.1039/c5ob00781j

文献信息

• Nucleophilic Substitution of Benzotriazolylalkyl Chlorides with Grignard Reagents: A Direct Route to Benzotriazoloalkyl(hetero)aromatic Compounds
  作者：Alan R. Katritzky

  DOI：10.1055/s-1999-3662

  日期：1999.8
• Reusable ionic liquid-catalyzed oxidative coupling of azoles and benzylic compounds via sp³ C–N bond formation under metal-free conditions
  作者：Wenbo Liu、Chenjiang Liu、Yonghong Zhang、Yadong Sun、Ablimit Abdukadera、Bin Wang、He Li、Xuecheng Ma、Zengpeng Zhang

  DOI：10.1039/c5ob00781j

  日期：——

  The heterocyclic ionic liquid-catalyzed direct oxidative amination of benzylic sp3 C–H bonds via intermolecular sp3 C–N bond formation for the synthesis of N-alkylated azoles under metal-free conditions is reported for the first time. The catalyst 1-butylpyridinium iodide can be recycled and reused with similar efficacies for at least eight cycles.

  杂环的离子液体催化的直接氧化的苄基胺化的SP 3 C-H键通过分子间的SP 3 C-N键的形成用于合成Ñ烷基化无金属的条件下唑类报道首次。催化剂碘化1-丁基吡啶鎓碘可以再循环并以相似的效率重复使用至少八个循环。
• Efficient Syntheses of 2-Functionalized Thiophenes, Cyclopent[<i>b</i>]thiophenes, and Polysubstituted Benzo[<i>b</i>]thiophenes from 2-(Benzotriazol-1-ylmethyl)thiophenes
  作者：Alan R. Katritzky、Larisa Serdyuk、Linghong Xie、Ion Ghiviriga

  DOI：10.1021/jo970672g

  日期：1997.9.1

  Diverse 2-(functionalized-alkyl)- and 2-alkenylthiophenes 2a,b, 4a,b, and 6a-d are prepared via the side chain elaboration of 2-(benzotriazol-1-ylmethyl)thiophenes 3a,b, themselves readily available from the condensation of 1-(hydroxymethyl)benzotriazole with thiophenes 1a,b. Treatment of 2-(benzotriazol-1-ylmethyl)thiophenes 3b and 5gj with styrenes in the presence of zinc bromide results in formal [3 + 2] cycloaddition to give in good yields substituted cyclopent[b]thiophenes 16a/17a, 16b/17b, and 18. Lithiation and 1,4-addition to a variety of alpha,beta-unsaturated ketones and aldehydes, and subsequent acid-catalyzed intramolecular cyclization followed by debenzotriazolylation-dehydration converts 3 and 5 to a range of polysubstituted benzo[b]thiophenes 19a-d and 25a-e in moderate to excellent yields. NOE difference spectroscopy and NMR H-1-C-13 long-range correlation support structures of types 19 and 25 and exclude those of type 26, thus confirming the cyclization pathway.