2-(3-acetyl-3-methyltriaz-1-en-1-yl)benzoic acid | 57601-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-acetyl-3-methyltriaz-1-en-1-yl)benzoic acid
• 英文别名: 3-acetyl-3-methyl-1-(2-carboxyphenyl)triazene；o-(N-Acetyl-N-methyltriazeno)benzoesaeure；2-[[Acetyl(methyl)amino]diazenyl]benzoic acid
• CAS: 57601-36-2
• 化学式: C₁₀H₁₁N₃O₃
• 分子量: 221.216
• InChiKey: FGOMAAGCPJQNKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-acetyl-3-methyltriaz-1-en-1-yl)benzoic acid 、 (E)-cinnamyl azide 以 乙腈 为溶剂， 反应 0.25h， 以58%的产率得到1-(γ-phenylallyl)benzotriazole
  参考文献：
  名称：

  A Photoinduced, Benzyne Click Reaction

  摘要：

  The [3 + 2] cycloaddition of azides and alkynes has proven invaluable across numerous scientific disciplines for imaging, cross-linking, and site-specific labeling among many other applications. We have developed a photoinitiated, benzyne-based [3 + 2] cycloaddition that is tolerant of a variety of functional groups as well as polar, protic solvents. The reaction is complete on the minute time scale using a single equivalent of partner azide, and the benzyne photo-precursor is stable for months under ambient light at room tempurature. Herein we report the optimization and scope of the photoinitiated reaction as well as characterization of the cycloaddition products.

  DOI：

  10.1021/ol500389t
• 作为产物：
  描述：

  [2-(2-methyliminohydrazinyl)phenyl]methanol 在 potassium permanganate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 17.0h， 生成 2-(3-acetyl-3-methyltriaz-1-en-1-yl)benzoic acid
  参考文献：
  名称：

  A Photoinduced, Benzyne Click Reaction

  摘要：

  The [3 + 2] cycloaddition of azides and alkynes has proven invaluable across numerous scientific disciplines for imaging, cross-linking, and site-specific labeling among many other applications. We have developed a photoinitiated, benzyne-based [3 + 2] cycloaddition that is tolerant of a variety of functional groups as well as polar, protic solvents. The reaction is complete on the minute time scale using a single equivalent of partner azide, and the benzyne photo-precursor is stable for months under ambient light at room tempurature. Herein we report the optimization and scope of the photoinitiated reaction as well as characterization of the cycloaddition products.

  DOI：

  10.1021/ol500389t

文献信息

• Reaction of benzothiazoline with benzyne - generation of novel heterocyclic sulfur ylide, benzothiazolinium s-ylide
  作者：Mikio Hori、Tadashi Kataoka、Hiroshi Shimizu、Norihiro Ueda

  DOI：10.1016/s0040-4039(01)81830-x

  日期：——

  A novel heterocyclic sulfur ylide, 2-t-butyl-3-methyl-1-phenylbenzothiazolinium ylide () was generated as an intermediate in the reaction of 2-t-butyl-3-(nethy1benzothiazoline () with benzyne. The S-ylide underwent a novel intermolecular [1,2] shift to give 2-t-butyl-3-methyl-2-phenylbenzothiazoline ().

  作为2-叔丁基-3-（nethy1苯并噻唑啉（）与苯炔反应）的中间体，生成了一种新型的杂环硫叶立德2-叔丁基-3-甲基-1-苯基苯并噻唑啉鎓叶立德（）。进行了新的分子间[1,2]转移，得到2-叔丁基-3-甲基-2-苯基苯并噻唑啉（）。
• Light-Induced Generation and Cycloaddition Reactions of Benzyne: Synthesis of Naphthoxindoles E and Annulated Indolizines
  作者：Haya Khan、Dhiraj Barman、Subhabrata Sen

  DOI：10.1021/acs.joc.4c00257

  日期：——

  dienophiles in numerous cycloaddition reactions. However, in situ generation of benzyne involves either base-mediated thermal reactions, low-temperature conditions, or metal-catalyzed reactions of substituted arenes. This limits the applicability of benzynes as suitable dipolarophiles in cycloaddition reactions. Herein, we have reported a UVA (365 nM)-induced in situ generation of benzynes (from triazenyl

  由于其高亲电子性质，苯炔在许多环加成反应中充当反应性亲二烯体。然而，苯炔的原位生成涉及碱介导的热反应、低温条件或取代芳烃的金属催化反应。这限制了苯炔作为环加成反应中合适的亲偶极试剂的应用。在此，我们报道了 UVA (365 nM) 诱导原位生成苯炔（来自三氮烯基苯甲酸），随后与适当的反应伙伴（如 N）发生 [4 + 2] Diels-Alder 和 [3 + 2] 环加成反应-保护的亚烷基羟吲哚羧酸盐和吡啶鎓叶立德分别以中等至优异的产率提供萘吲哚E和吡啶并[2,1- a ]异吲哚。反应在室温和无试剂反应条件下进行。这些构件中的每一个都具有药学相关性；因此，这凸显了获取此类化合物的有趣策略。
• Maki,Y. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 553 - 557
  作者：Maki,Y. et al.

  DOI：——

  日期：——
• A Photoinduced, Benzyne Click Reaction
  作者：Adam W. Gann、Jon W. Amoroso、Vincent J. Einck、Walter P. Rice、James J. Chambers、Nathan A. Schnarr

  DOI：10.1021/ol500389t

  日期：2014.4.4

  The [3 + 2] cycloaddition of azides and alkynes has proven invaluable across numerous scientific disciplines for imaging, cross-linking, and site-specific labeling among many other applications. We have developed a photoinitiated, benzyne-based [3 + 2] cycloaddition that is tolerant of a variety of functional groups as well as polar, protic solvents. The reaction is complete on the minute time scale using a single equivalent of partner azide, and the benzyne photo-precursor is stable for months under ambient light at room tempurature. Herein we report the optimization and scope of the photoinitiated reaction as well as characterization of the cycloaddition products.