2-(4-methoxybenzyl)-5-phenyl-2H-tetrazole | 312319-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-methoxybenzyl)-5-phenyl-2H-tetrazole
• 英文别名: 2H-Tetrazole, 2-(4-methoxybenzyl)-5-phenyl-；2-[(4-methoxyphenyl)methyl]-5-phenyltetrazole
• CAS: 312319-27-0
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: LTEHIGRGQQGERP-UHFFFAOYSA-N

物化性质

• 沸点：
  465.8±47.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-methoxybenzyl)-5-phenyl-2H-tetrazole 、 4-溴苄基乙酸酯 在 N-甲基吡咯烷酮 、 [RuCl2(benzene)]2 、 potassium carbonate 、 三苯基膦 作用下， 反应 12.0h， 以21%的产率得到{2'-[2-(p-methoxybenzyl)-2H-tetrazol-5-yl]biphenyl-4-yl}methyl acetate
  参考文献：
  名称：

  Synthesis of Angiotensin II Receptor Blockers by Means of a Catalytic System for C–H Activation

  摘要：

  A highly efficient catalytic system for C-H activation has been worked out that involves inexpensive RuCl3.xH(2)O and a specific amount of PPh3. This procedure has been successfully applied to a practical synthesis of angiotensin II receptor blockers (ARBs). The residual ruthenium that existed in the reaction mixture was thoroughly removed by treatment with properly selected metal scavengers. The new process permits ready access to the important class of drugs in a highly atom-economical and sustainable manner.

  DOI：

  10.1021/jo202041e
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 lithium tert-butoxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 21.0h， 生成 1-(p-methoxybenzyl)-5-phenyl-1H-tetrazole 、 2-(4-methoxybenzyl)-5-phenyl-2H-tetrazole
  参考文献：
  名称：

  N-甲苯磺酰腙与四唑的偶联：2,5-二取代-2H-四唑的区域选择性合成

  摘要：

  报道了一种新的区域选择性合成 2,5-二取代-2 H-四唑的方法，该方法是在具有优异官能团耐受性的热活化条件下，在不同碱存在下，通过 N-甲苯磺酰腙和四唑的C-N 偶联。

  DOI：

  10.1002/ejoc.202201103

文献信息

• Late-stage azolation of benzylic C‒H bonds enabled by electrooxidation
  作者：Zhixiong Ruan、Zhixing Huang、Zhongnan Xu、Shaogao Zeng、Pengju Feng、Ping-Hua Sun

  DOI：10.1007/s11426-020-9938-9

  日期：2021.5

  The installation of azoles via C-H/N-H cross-coupling is significantly underdeveloped, particularly in benzylic C-H azolation due to the requirement for external chemical oxidants and the challenge in controlling the site- and chemo-selectivity. Herein, a late-stage azolation of benzylic C-H bonds enabled by electrooxidation is described, which proceeds in an undivided cell under mild, catalyst- and

  唑类的安装通过由于对外部化学氧化剂的要求以及控制位点和化学选择性的挑战，CH / NH交叉偶联显着欠发达，特别是在苄基CH偶氮化反应中。在本文中，描述了通过电氧化实现的苄基CH键的后期偶氮化，其在温和，无催化剂和无化学氧化剂的反应条件下在未分格的电池中进行。该策略可选择性地在伯，仲，甚至具有挑战性的叔苄基位置上实现CH偶氮化。我们的方法具有非凡的合成效用，其突出的特点是易于扩展，不引起产品过度氧化，并具有适用范围广的有价值的官能团。该方法可直接用于在高度官能化的药物分子上安装苄基和唑基。
• PROCESS FOR PRODUCTION OF BIPHENYL DERIVATIVE
  申请人：Seki Masahiko

  公开号：US20120232283A1

  公开（公告）日：2012-09-13

  The invention provides a production method of a biaryltetrazole derivative useful as an intermediate for an angiotensin II receptor antagonist. The method comprises reacting an aryltetrazole derivative with a benzene derivative, deprotecting or reducing the resulting compound, and halogenating the deprotected or reduced compound

  该发明提供了一种生产方法，用作肾素II受体拮抗剂的中间体的双芳基四唑衍生物。该方法包括将芳基四唑衍生物与苯衍生物反应，去保护或还原所得化合物，并对去保护或还原的化合物进行卤代反应。
• Transition-Metal-Free Direct Alkylation of Aryl Tetrazoles via Intermolecular Oxidative C–N Formation
  作者：Liang Wang、Kaiqiang Zhu、Qun Chen、Mingyang He

  DOI：10.1021/jo502283h

  日期：2014.12.5

  A transition-metal-free synthetic approach for constructing alkylated aryl tetrazoles has been developed using n-Bu4NI as the catalyst and t-BuOOH as the oxidant. It involves the direct C-N bond formation through sp(3) C-H activation. A wide range of benzylic C-H substrates (or alkyl ethers) and aryl tetrazoles undergo this reaction smoothly to deliver the corresponding products in good yields.
• Bu₄NI Catalyzed C–N Bond Formation via Cross-Dehydrogenative Coupling of Aryl Ethers (C_sp3–H) and Tetrazoles (N–H)
  作者：Suresh Rajamanickam、Ganesh Majji、Sourav Kumar Santra、Bhisma K. Patel

  DOI：10.1021/acs.orglett.5b02749

  日期：2015.11.20

  Intermolecular C-N bond formations via cross-dehydrogenative coupling (CDC) of aryl ethers and tetrazoles have been developed under a metal-free condition. In the presence of catalytic amount of tetrabutylammonium iodide (TBAI) and aqueous TBHP, aryl ethers coupled efficiently with tetrazoles to afford hemiaminal ethers. This strategy showed high level of regioselectivity for substrates possessing multiple sp(3) C-H bonds adjacent to the ethereal oxygen.
• US8530506B2
  申请人：——

  公开号：US8530506B2

  公开（公告）日：2013-09-10