2-azido-4,5-(dimethoxy)benzyl alcohol | 197525-02-3

• 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-azido-4,5-(dimethoxy)benzyl alcohol
• 英文别名: (2-Azido-4,5-dimethoxyphenyl)methanol；(2-azido-4,5-dimethoxyphenyl)methanol
• CAS: 197525-02-3
• 化学式: C₉H₁₁N₃O₃
• 分子量: 209.205
• InChiKey: NIJXQKVFHBYZQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-azido-4,5-(dimethoxy)benzyl alcohol 在 magnesium sulfate 、 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Intramolecular [2 + 2] cycloaddition of ketenimines with imines. Synthesis and chemical behaviour of azeto[2,1-b]quinazolines

  摘要：

  Azeto[2,1-b]quinazolines 5 have been prepared by the novel intramolecular [2 + 2] cycloaddition reaction of ketenimines with imines. The applicability and limitations of the synthetic methodology, and explorations on the reactivity of compounds 5 are discussed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00855-7
• 作为产物：
  描述：

  6-硝基藜芦醛 在 palladium on activated charcoal sodium tetrahydroborate 、 硫酸 、 氢气 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 18.5h， 生成 2-azido-4,5-(dimethoxy)benzyl alcohol
  参考文献：
  名称：

  Intramolecular [2 + 2] cycloaddition of ketenimines with imines. Synthesis and chemical behaviour of azeto[2,1-b]quinazolines

  摘要：

  Azeto[2,1-b]quinazolines 5 have been prepared by the novel intramolecular [2 + 2] cycloaddition reaction of ketenimines with imines. The applicability and limitations of the synthetic methodology, and explorations on the reactivity of compounds 5 are discussed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00855-7

文献信息

• Synthesis of Diverse Benzotriazoles from Aryne Precursors Bearing an Azido Group via Inter- and Intramolecular Cycloadditions
  作者：Suguru Yoshida、Takamoto Morita、Takamitsu Hosoya

  DOI：10.1246/cl.160349

  日期：2016.7.5

  etherification. Various bis-1,2,3-triazoles containing a benzotriazole skeleton were obtained via sequential azide–alkyne and azide–aryne cycloadditions. Intramolecular azido–aryne cycloaddition, conducted using the same starting materials, afforded new types of ring-fused benzotriazoles. In the latter case, the reaction proceeded efficiently even though the regioorientation of the azido group was the reverse

  从各种 3-（叠氮烷氧基）芳烃前体合成了多种苯并三唑，这些前体很容易通过光信醚化制备。通过连续的叠氮化物-炔烃和叠氮化物-芳烃环加成反应获得了各种含有苯并三唑骨架的双-1,2,3-三唑。使用相同的起始材料进行分子内叠氮-芳烃环加成，得到了新型的稠环苯并三唑。在后一种情况下，即使叠氮基的区域取向与通常在 3-烷氧基芳烃和叠氮化物之间的分子间反应中观察到的方向相反，反应也能有效进行。
• Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling
  作者：Yury N. Kotovshchikov、Stepan S. Tatevosyan、Gennadij V. Latyshev、Nikolay V. Lukashev、Irina P. Beletskaya

  DOI：10.1055/a-1623-2333

  日期：2022.1

  Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C–O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C–I

  一种方便的方法来组装 1,2,3-三唑融合的 4H-3,1-苯并恶嗪。多种醇系 5-碘三唑，可通过 Cu 催化 (3+2)-环加成的改进方案轻松获得，被用作目标稠合杂环的前体。分子内 C-O 偶联在无碱介导的过渡金属条件下有效进行，环化产物的产率高达 96%。通过在 100 °C 的乙腈中使用 Na2CO3 来抑制 C-I 键的竞争性还原裂解。这种实用且具有成本效益的程序具有广泛的底物范围和宝贵的官能团耐受性。
• Synthesis of polymethoxy-substituted triazolobenzoxazepines
  作者：S. Yu. Bukhvalova、M. A. Ivanov、Yu. B. Malysheva、A. Yu. Fedorov

  DOI：10.1134/s1070428016100183

  日期：2016.10

  A new approach has been proposed for the synthesis of polymethoxy-substituted [1,2,3]triazolo-[1,5-a][4,1]benzoxazepines starting from 2-bromo-4,5-dimethoxy- and 2-bromo-3,4,5-dimethoxybenzyl alcohols with thermal [3 + 2]-dipolar cycloaddition as the key stage.
• Intramolecular [2 + 2] cycloaddition of ketenimines with imines. Synthesis and chemical behaviour of azeto[2,1-b]quinazolines
  作者：Mateo Alajarín、Pedro Molina、Angel Vidal、Fulgencio Tovar

  DOI：10.1016/s0040-4020(97)00855-7

  日期：1997.9

  Azeto[2,1-b]quinazolines 5 have been prepared by the novel intramolecular [2 + 2] cycloaddition reaction of ketenimines with imines. The applicability and limitations of the synthetic methodology, and explorations on the reactivity of compounds 5 are discussed. (C) 1997 Elsevier Science Ltd.