5-(2'-methoxyphenoxy)-1-phenyl-1H-tetrazole | 17743-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2'-methoxyphenoxy)-1-phenyl-1H-tetrazole
• 英文别名: 5-(2-Methoxyphenoxy)-1-phenyltetrazole
• CAS: 17743-22-5
• 化学式: C₁₄H₁₂N₄O₂
• 分子量: 268.275
• InChiKey: DBRULZRSXDACNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2'-methoxyphenoxy)-1-phenyl-1H-tetrazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 40.0h， 以39%的产率得到苯甲醚
  参考文献：
  名称：

  A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow

  摘要：

  sA low-energy, high-selectivity approach to the catalytic hydrodeoxygenation of phenols is reported using batch or continuous flow methods to react 3 equiv of phenol with cyanuric chloride then hydrogenolyzing the triarylcyanurate intermediate to give 3 equiv of deoxo aromatic. The use of cyanuric chloride compares favorably with existing activation methods, showing improved scalability, atom efficiency, and economics. The scope of both the activation and hydrogenolysis stages are explored using lignin-related phenols. Initial development has identified that continuous stir tank reactors (CSTRs) enable a multiphasic process for converting guaiacol to anisole and at steady state overcome the catalyst deactivation issues observed in batch, seemingly caused by the cyanurate byproduct. Green chemistry aspects and the potential for industrial adoption are discussed.

  DOI：

  10.1021/acs.oprd.6b00314
• 作为产物：
  描述：

  2-methoxyphenyl mesylate 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 41.0h， 生成 5-(2'-methoxyphenoxy)-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow

  摘要：

  sA low-energy, high-selectivity approach to the catalytic hydrodeoxygenation of phenols is reported using batch or continuous flow methods to react 3 equiv of phenol with cyanuric chloride then hydrogenolyzing the triarylcyanurate intermediate to give 3 equiv of deoxo aromatic. The use of cyanuric chloride compares favorably with existing activation methods, showing improved scalability, atom efficiency, and economics. The scope of both the activation and hydrogenolysis stages are explored using lignin-related phenols. Initial development has identified that continuous stir tank reactors (CSTRs) enable a multiphasic process for converting guaiacol to anisole and at steady state overcome the catalyst deactivation issues observed in batch, seemingly caused by the cyanurate byproduct. Green chemistry aspects and the potential for industrial adoption are discussed.

  DOI：

  10.1021/acs.oprd.6b00314

文献信息

• Rapid Cesium Fluoride Catalyzed Synthesis of 5-Aryloxy-1-phenyl-1Htetrazoles via Nucleophilic Aromatic Substitution
  作者：Khalid Mohammed Khan、Itrat Fatima、Shahnaz Perveen、Syed Muhammad Saad

  DOI：10.2174/1570178617999200728211046

  日期：2021.5

  A nucleophilic aromatic substitution via a new and facile cesium fluoride catalyzed synthetic approach to get 5-aryloxy-1-phenyl-1H-tetrazoles was developed. Dual usage of cesium fluoride as a nucleophilic catalyst as well as an electrophilic catalyst afforded the desired products at room temperature in a short reaction time without purification in high yields. This simple but useful reaction may be

  通过一种新的，简便的氟化铯催化合成方法，开发了亲核芳香族取代基，从而获得了5-芳氧基-1-苯基-1H-四唑。氟化铯作为亲核催化剂和亲电子催化剂的双重使用在室温下以较短的反应时间提供了所需的产物，而没有以高收率进行纯化。这种简单但有用的反应可能是合成四唑基醚的一种快速而可靠的策略。
• Metal-assisted reactions—13
  作者：Brendan J. Hussey、Robert A.W. Johnstone、Jan D. Entwistle

  DOI：10.1016/0040-4020(82)80091-4

  日期：1982.1

  Previous work has shown that, after converting phenols into suitable phenolic ethers, the aromatic CH bond of the original phenol can be reductively cleaved heterogeneously to give a CH bond through the use of molecular hydrogen or hydrogen donors together with a transition metal catalyst. The present work provides a method for selectively replacing a phenolic OH group by H in just a few minutes

  先前的工作表明，在将酚转化为合适的酚醚后，可以通过使用分子氢或氢供体以及过渡金属，异质地裂解原始酚的芳族CH键，使其异质裂解，形成CH键。催化剂。与先前使用氢供体所需的2至4小时以及在分子氢所需的压力下的数小时相比，本发明提供了一种在短短几分钟内用H选择性地取代酚式OH基的方法。各种基团均适用于从苯酚制备所需的酚醚，但最好的基团是具有强吸电子性的杂芳族实体。溶剂似乎在这种非均相反应中起着重要作用，并对其机理进行了讨论。
• Observation of burst kinetics in heterogeneous catalytic transfer hydrogenolysis
  作者：Donald Bethell、Robert A. W. Johnstone、Peter J. Price

  DOI：10.1039/c39850000303

  日期：——

  Arene formation by catalytic transfer hydrogenolysis of aryl tetrazolyl ethers in the liquid phase shows biphasic concentration–time curves indicating rate-limiting dissociation of heterogeneous complexes between catalyst and tetrazolone produced under steady state conditions.

  芳基四唑基醚在液相中通过催化转移氢解而形成的芳烃显示出双相浓度-时间曲线，表明在稳态条件下生成的催化剂与四唑酮之间非均相络合物的限速解离。
• Tetrazoles. 33. New method for obtaining functionally substituted tetrazoles
  作者：M. A. Gol'tsberg、G. I. Koldobskii

  DOI：10.1007/bf01169961

  日期：——
• ENTWISTLE I. D.; HUSSEY B. J.; JOHNSTONE R. A. W., TETRAHEDRON LETT., 1980, 21, NO 49, 4747-4748
  作者：ENTWISTLE I. D.、 HUSSEY B. J.、 JOHNSTONE R. A. W.

  DOI：——

  日期：——