1-(3-methylbenzyl)-1H-benzo[d][1,2,3]triazole | 142087-15-8

• 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-(3-methylbenzyl)-1H-benzo[d][1,2,3]triazole
• 英文别名: 1-[(3-Methylphenyl)methyl]-1H-1,2,3-benzotriazole；1-[(3-methylphenyl)methyl]benzotriazole
• CAS: 142087-15-8
• 化学式: C₁₄H₁₃N₃
• mdl: MFCD00971348
• 分子量: 223.277
• InChiKey: YAWKUAOZLUPNMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-methylbenzyl)-1H-benzo[d][1,2,3]triazole 在 正丁基锂 、 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  A novel synthesis of 4,5-diaryl-6-arylamino-2,3-benzo-1,3a,6a-triazapentalenes

  摘要：

  Treatment of N-alkyl- and N-aryl-imines of 2,3-diaryl- and 2-alkyl-3-aryl-3-(benzotriazol-1-yl)propenals with trifluoroacetic anhydride in THF at room temperature gave 5-alkyl-4-aryl-6-[N-alkyl (and aryl)-N-trifluoroacetyl]amino-2,3-benzo-1,3a,6a-triazapentalenes in moderate to good yields. On heating triazapentalenes having R-2 = aryl in MeOH at reflux, detrifluoroacetylation of triazapentalene occurred to give title compounds in good yields. However, the same treatment of triazapentalenes having R-2=alkyl did not give the corresponding detrifluoroacetylation product. The title compounds and 5-alkyl-4-aryl-6-(N-alkyl-N-trifluoroacetyl)amino-2,3-benzo-1,3a,6a-triazapentalenes were found to be good precursors for the synthesis of 1-(o-aminophenyl)-3-arylamino-4-alkyl (and aryl)-5-arylpyrazoles and 1-(o-aminophenyl)-3-(N-alkyl-N-trifluoroacetyl)amino-4-alkyl (and aryl)-5-arylpyrazoles, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.012
• 作为产物：
  描述：

  2-(三甲硅基)苯酚 在 18-冠醚-6 、 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 生成 1-(3-methylbenzyl)-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  Development and Application of O-(Trimethylsilyl)aryl Fluorosulfates for the Synthesis of Arynes

  摘要：

  A class of o-(trimethylsilyl)aryl fluorosulfates was synthesized by a concise method and successfully used as aryne precursors for the first time. Different trapping agents such as azides, furans, and acyl acetoacetates could successfully react with the aryne precursors under mild conditions with good to excellent yields.

  DOI：

  10.1021/acs.joc.5b00923

文献信息

• 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。
• Oxidation of 1-[(aryl)(phenylseleno)methyl]-, 1-[(aryl)(arylthio)-(phenylseleno)methyl]-, and l-[(aryl)(diphenylseleno)methyl]benzotriazoles with<i>m</i>-chloroperbenzoic acid
  作者：Yoon Ho Kang、Kyongtae Kim

  DOI：10.1002/jhet.5570340617

  日期：1997.11

  During the last decade, benzotriazole (1) has received much attention as an excellent synthetic auxiliary [1]. Recently Katritzky, et al. [2] studied the oxidation of 1-(phenylthiomethyl)benzotriazole (2a) and 1-(2-phenyl-1-phenylthioethyl)benzotriazole (2b) and obtained their sulfones and sulfoxides by treatment with wj-chloroperbenzoic acid (m-CPBA) and sodium periodate, respectively. No compounds

  在过去的十年中，苯并三唑（1）作为一种出色的合成助剂受到了广泛的关注[1]。最近，Katritzky等人。[ 2 ]研究了1-（phenylthiomethyl）benzotriazole（2a）和1-（2-phenyl-1-phenylthioethyl）benzotriazole（2b）的氧化，并通过wj-氯过苯甲酸（m -CPBA）处理获得了它们的砜和亚砜。和高碘酸钠。没有分离出衍生自前述化合物的α-碳和N-1原子之间的杂位裂解的化合物。
• 一种简单高效的二芳香炔烃合成方法
  申请人：重庆文理学院

  公开号：CN112645784B

  公开（公告）日：2023-04-21

  本发明实施例公开了一种简单高效的二芳香炔烃合成方法，包括：以芳甲基苯并三氮唑和芳香醛为原料，在双(三甲基硅基)氨基盐MN(SiMe3)2的作用下，经过加成和双β‑消除反应，一锅法合成二芳香炔烃。本发明中所使用的原料和化学试剂都易于得到，且反应条件温和、操作简单、底物普适性好、产品收率高，是一种简单高效的二芳香炔烃合成方法。
• Facile one-pot synthesis of diarylacetylenes from arylaldehydes <i>via</i> an addition-double elimination process
  作者：Jianyang Chen、Xuan Zhang、Jiajun Wu、Rui Wang、Chunlin Lei、Yanan An

  DOI：10.1039/d1ob00627d

  日期：——

  A practical one-pot protocol has been developed to synthesize diarylacetylenes from arylaldehydes by treatment with 1-(arylmethyl)benzotriazoles and LiN(SiMe3)2. The reaction proceeded through imine formation, Mannich-type addition and double elimination to deliver products in up to 99% yields with broad substrate scope. In addition, gram-scale synthesis of 1-bromo-4-(phenylethynyl)benzene has been

  已经开发了一种实用的一锅法，通过用 1-(芳甲基)苯并三唑和 LiN(SiMe 3 ) 2处理从芳醛合成二芳基乙炔。该反应通过亚胺形成、曼尼希型加成和双消除进行，以提供高达 99% 的产率和广泛的底物范围。此外，已经证明了 1-溴-4-(苯乙炔基)苯的克级合成。
• Phosphonic acid derivatives as inhibitors of protein tyrosine phosphatase 1B (PTP-1B)
  申请人：——

  公开号：US20020058644A1

  公开（公告）日：2002-05-16

  The invention encompasses the novel class of compounds represented by formula I, which are inhibitors of the PTP-1B enzyme. 1 The invention also encompasses pharmaceutical compositions and methods of treating or preventing PTP-1B mediated diseases, including diabetes, obesity, and conditions related to diabetes.

  该发明涵盖了由公式I代表的新型化合物类别，这些化合物是PTP-1B酶的抑制剂。该发明还涵盖了药物组合物和治疗或预防PTP-1B介导的疾病的方法，包括糖尿病、肥胖以及与糖尿病相关的疾病。