1-benzyl-5-(4-methoxyphenyl)-1H-tetrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-5-(4-methoxyphenyl)-1H-tetrazole
• 英文别名: 1-Benzyl-5-(4-methoxyphenyl)tetrazole
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: AHQSPQXGDQFBEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  1-benzyl-5-(4-methoxyphenyl)-1H-tetrazole 在 盐酸 、 palladium on carbon 、 锌 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以49.4 mg的产率得到5-(4-甲氧基苯基)-1H-四唑
  参考文献：
  名称：

  One-Pot Suzuki-Hydrogenolysis Protocol for the Modular Synthesis of 2,5-Diaryltetrazoles

  摘要：

  2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the practical synthesis of a library of these derivatives. Herein, we disclose the development of a modular approach toward 2,5-diaryltetrazoles compatible with an array-type protocol, facilitated by a tandem Suzuki-hydrogenolysis approach.

  DOI：

  10.1021/acs.joc.0c00807
• 作为产物：
  描述：

  N-苄基-4-甲氧基苯甲酰胺 在 四丁基溴化铵 氯化亚砜 、 sodium azide 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 1-benzyl-5-(4-methoxyphenyl)-1H-tetrazole
  参考文献：
  名称：

  1,5-二取代四唑的高效合成

  摘要：

  一种由亚氨基苯并三唑合成 1,5-二取代四唑的通用方法，反应条件温和，反应时间短。

  DOI：

  10.1055/s-2007-966001

文献信息

• Highly Efficient Synthesis of 5-Substituted 1H-Tetrazoles Catalyzed by Cu-Zn Alloy Nanopowder, Conversion into 1,5- and 2,5-Disubstituted Tetrazoles, and Synthesis and NMR Studies of New Tetrazolium Ionic Liquids
  作者：Gopalakrishnan Aridoss、Kenneth K. Laali

  DOI：10.1002/ejoc.201100957

  日期：2011.11

  synthesize several novel tetrazolium ionic liquids (ILs) with EtSO4–, OTf–, and NTf2– counterions. Whereas alkylation of the 2,5-dialkyltetrazoles selectively gave the N-4 alkylated onium salts, with the 1,5-dialkyl derivatives approximately 1:1 mixtures of two tetrazolium salts were formed by alkylation at N-3 and N-4. The triflate and ethyl sulfate salts are room-temperature ILs that are hydrophilic, whereas

  在Cu-Zn合金纳米粉体作为催化剂存在下，通过腈类RCN和NaN3之间的[3+2]环加成反应合成了一系列5-取代的1H-四唑。然后将 1,5-二丁基、1-丁基-5-己基、2,5-二丁基和 2-丁基-5-己基衍生物用作结构单元，用 EtSO4– 合成几种新型四唑鎓离子液体 (IL)， OTf– 和 NTf2– 反离子。而 2,5-二烷基四唑的烷基化选择性地产生 N-4 烷基化鎓盐，而 1,5-二烷基衍生物通过在 N-3 和 N-4 处烷基化形成大约 1:1 的两种四唑盐混合物。三氟甲磺酸盐和乙基硫酸盐是亲水的室温离子液体，而 NTf2 盐是低熔点离子液体并且是疏水的。
• Single-Component Phosphinous Acid Ruthenium(II) Catalysts for Versatile C−H Activation by Metal-Ligand Cooperation
  作者：Daniel Zell、Svenja Warratz、Dmitri Gelman、Simon J. Garden、Lutz Ackermann

  DOI：10.1002/chem.201504851

  日期：2016.1.22

  Well‐defined ruthenium(II) phosphinous acid (PA) complexes enabled chemo‐, site‐, and diastereoselective C−H functionalization of arenes and alkenes with ample scope. The outstanding catalytic activity was reflected by catalyst loadings as low as 0.75 mol %, and the most step‐economical access reported to date to angiotensin II receptor antagonist blockbuster drugs. Mechanistic studies indicated a

  明确定义的次膦酸亚膦酸钌（II）配合物可在广泛的范围内实现芳烃和烯烃的化学，位点和非对映选择性CH功能化。低至0.75 mol％的催化剂载量反映了其出色的催化活性，并且据报道是迄今为止获得血管紧张素II受体拮抗剂重磅炸弹药物最省钱的途径。机理研究表明，通过单电子转移（SET）型基本过程可发生动力学相关的C-X裂解，并为PA辅助的C-H钌化步骤提供了证据。
• Pd(<scp>ii</scp>)-catalyzed, controllable C–H mono-/diarylation of aryl tetrazoles: concise synthesis of Losartan
  作者：Yan-Jun Ding、Yan Li、Sheng-Yu Dai、Quan Lan、Xi-Sheng Wang

  DOI：10.1039/c4ob02453b

  日期：——

  A palladium(II)-catalyzed C-H arylation directed by tetrazole, a metabolically stable surrogate for the carboxylic acid group in drug design, has been developed. Excellent mono-/di-selectivity was achieved through adjustment of the protecting site on the tetrazole ring. The synthetic utility of this new transformation was demonstrated in the concise total synthesis of Losartan.

  已经开发了由四唑（在药物设计中羧酸基团的代谢稳定替代物）指导的钯（II）催化的CH芳基化反应。通过调节四唑环上的保护位获得了极好的单/双选择性。氯沙坦的简明全合成显示了这种新转化的合成效用。
• Amino Acid Ligands for Ruthenium(II)-Catalyzed C-H Arylation of Aryltetrazoles with Chlorides: Expedient Access to Antihypertension Drugs
  作者：Jonathan Hubrich、Lutz Ackermann

  DOI：10.1002/ejoc.201600742

  日期：2016.8

  Versatile ruthenium(II) complexes derived from amino acids enabled the first general C–H arylations of aryltetrazoles with inexpensive aryl chlorides. The user-friendly Piv-Val-OH-based ruthenium(II) catalyst was characterized by a broad substrate scope, excellent functional group tolerance, and high catalytic activity. Thereby, the ruthenium(II) catalysis set the stage for the step-economical preparation

  源自氨基酸的多功能钌​​ (II) 配合物使芳基四唑与廉价的芳基氯化物首次实现了通用的 C-H 芳基化。用户友好的 Piv-Val-OH 基钌 (II) 催化剂的特点是底物范围广、官能团耐受性好、催化活性高。因此，钌 (II) 催化为重磅抗高血压药物缬沙坦的分步经济制备奠定了基础，同时在 C-H 芳基化机制中显示出独特的稳健性。
• REMEDIES FOR STRESS DISEASES COMPRISING MITOCHONDRIAL BENZODIAZEPINE RECEPTOR ANTAGONISTS
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1438973A1

  公开（公告）日：2004-07-21

  A pharmaceutical composition for the prophylaxis and/or treatment of diseases induced, exacerbated or reignited by stressors comprising the compound of formula (I) wherein all symbols have the same meanings as described in the specification, etc. as an active ingredient.

  一种用于预防和/或治疗由应激源诱发、加重或复燃的疾病的药物组合物，由式 (I) 化合物组成 其中所有符号的含义与说明书中所述的相同等作为活性成分。