4-(2-azido-phenyl)-but-3-en-2-one | 1255952-14-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-(2-azido-phenyl)-but-3-en-2-one
• 英文别名: 4-(2-Azidophenyl)but-3-en-2-one
• CAS: 1255952-14-7
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: BBKONUHDKXPEFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-azido-phenyl)-but-3-en-2-one 在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 1-(3,4-dihydro-3-phenyl-2-(1H-1,2,4-triazol-1-yl)quinazolin-4-yl)-propan-2-one
  参考文献：
  名称：

  Synthesis, Fungicidal Activity, and Sterol 14α-Demethylase Binding Interaction of 2-Azolyl-3,4-dihydroquinazolines on Penicillium digitatum

  摘要：

  A series of new 2-azolyl-3,4-dihydroquinazolines 6 was synthesized by direct cyclization of imidazole or 1,2,4-triazole with carbodiimides 4, which were obtained from aza-Wittig reaction of iminophosphorane 3 with isocyanate. The preliminary bioassay results demonstrated that most of the 2-imidazolyl-3,4-dihydroquinazolines 6a-6i exhibited good to significant fungicidal activity against Penicillium digitatum, whereas 2-triazolyl-3,4-dihydroquinazolines 6j-6t exhibited low fungicidal activity. Some of the 2-imidazolyl-3,4-dihydroquinazolines 6a-6i also exhibited strong binding interaction with the cytochrome P450-dependent sterol 14 alpha-demethylase (CYP51). For example, compound 6e showed the best fungicidal activity against P. digitatum with IC50 = 4.14 mu g/mL and the best CYP51 binding activity with K-d = 0.34 mu g/mL, both superior to those of the agricultural fungicide triadimefon.

  DOI：

  10.1021/jf305355u
• 作为产物：
  描述：

  邻硝基苯甲醛 在 六甲基磷酰三胺 、 sodium azide 作用下， 以 乙醇 为溶剂， 生成 4-(2-azido-phenyl)-but-3-en-2-one
  参考文献：
  名称：

  邻-叠氮基肉桂酰基衍生物的光化学：溶剂控制下 2-酰化吲哚和 2-取代喹啉的简便和模块化合成

  摘要：

  评估邻-叠氮基肉桂酰基化合物的光促进潜力用于杂环合成。根据溶剂的性质，在质子惰性条件下获得 2-酰化吲哚，而使用质子介质产生 2-取代喹啉。这种不含金属的方法的合成意义在于，通过简单地改变溶剂，反应结果可以针对不同的关键杂环支架。

  DOI：

  10.1055/s-0036-1590861

文献信息

• Synthesis of 2H-pyrrolo[3,4-C]quinoline via an Aldol/Van Leusen/Staudinger/aza-Wittig sequence
  作者：Yu-Qing Shi、Li-De Liao、Ping He、Yang-Gen Hu、Hua Cheng、Song Wang、Jun-Jun Wu

  DOI：10.1080/00397911.2016.1204462

  日期：2016.8.17

  Leusen/Staudinger/aza-Wittig reaction for the preparation of the derivatives of 2H-pyrrolo[3,4-c]quinolines from 2-azidobenzaldehyde, acetyl compounds, and tosylmethyl isocyanide was developed. The process involves an aldol condensation of 2-azidobenzaldehyde with acetyl compound in base, a van Leusen reaction to form the key pyrrole intermediates, and then a Staudinger and intramolecular aza-Wittig reaction occurred

  摘要 建立了一种从 2-叠氮苯甲醛、乙酰化合物和甲苯磺酰甲基异氰化物制备 2H-吡咯并 [3,4-c] 喹啉衍生物的 aldol/van Leusen/Staudinger/aza-Wittig 反应。该过程包括2-叠氮基苯甲醛在碱中与乙酰基化合物的羟醛缩合，van Leusen反应形成关键的吡咯中间体，然后在加入三苯基膦的情况下发生Staudinger和分子内氮杂-Wittig反应以完成吡咯的形成。 3,4-c]喹啉环的高产率。图形概要
• The organocatalytic two-step synthesis of diversely functionalized tricyclic tetrazoles
  作者：Xiong Huang、Ping Li、Xin-Sheng Li、Dong-Cheng Xu、Jian-Wu Xie

  DOI：10.1039/c0ob00272k

  日期：——

  The diversely functionalized tricyclic tetrazoles were synthesised from readily available substrates via intramolecular 1,3-dipolar cycloaddition as the key step in good yields (53–78% yield for two steps) with high enantioselectivities (81–99% ee).

  通过分子内 1,3-二极环化反应这一关键步骤，以容易获得的底物为原料，合成了具有多种功能的三环四唑，且产量高（两个步骤的产量均为 53-78%），对映选择性高（81-99% ee）。
• An Efficient Protocol for the Synthesis of Pyrazolo[1,5-c]quinazolines by a Staudinger–Aza-Wittig–Dehydroaromatization Sequence
  作者：Zhilin Ren、Ping He、Mingxian Xu、An Chen、Jiying Qiu、Mingming Zu、Yi Zhang、Jiayi Wang

  DOI：10.1055/a-1579-1692

  日期：2021.11

  The one-pot synthesis of azide-substituted dihydropyrazoles in isopropanol was performed by using chalcones, hydrazine hydrate, and an acyl chloride at 0 ℃. Subsequent Staudinger–aza-Wittig–dehydroaromatization reactions of the products with methyl(diphenyl)phosphine were also investigated for further application in the construction of pyrazolo[1,5-c]quinazolines.

  以查耳酮、水合肼和酰氯为原料，在0 ℃下在异丙醇中一锅法合成叠氮化物取代的二氢吡唑类化合物。还研究了产物与甲基（二苯基）膦的后续 Staudinger-aza-Wittig-脱氢芳构化反应，以进一步应用于构建吡唑并 [1,5-c] 喹唑啉。
• Rh₂(II)-Catalyzed Nitro-Group Migration Reactions: Selective Synthesis of 3-Nitroindoles from β-Nitro Styryl Azides
  作者：Benjamin J. Stokes、Sheng Liu、Tom G. Driver

  DOI：10.1021/ja111060q

  日期：2011.4.6

  Rhodium carboxylate complexes (1 mol %) catalyze the migration of electron-withdrawing groups to selectively produce 3-substituted indoles from beta-substituted styryl azides. The relative order of migratorial aptitude for this transformation is ester << amide < H < sulfonyl < benzoyl << nitro.