1-{2'-(1-benzyl-1H-tetrazol-5-yl)-4'-methyl-[1,1'-biphenyl]-4-yl}ethan-1-one | 1432044-45-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-{2'-(1-benzyl-1H-tetrazol-5-yl)-4'-methyl-[1,1'-biphenyl]-4-yl}ethan-1-one
• 英文别名: 1-{2'-(1-benzyl-1H-tetrazol-5-yl)-4'-methyl-[1,1'-biphenyl]-4-yl}ethanone；1-[4-[2-(1-Benzyltetrazol-5-yl)-4-methylphenyl]phenyl]ethanone
• CAS: 1432044-45-5
• 化学式: C₂₃H₂₀N₄O
• 分子量: 368.438
• InChiKey: SADUJNJKYBJYJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-benzyl-5-(m-tolyl)-1H-tetrazole 、 4-溴苯乙酮 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 2,4,6-三甲基苯甲酸 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以65%的产率得到1-{2'-(1-benzyl-1H-tetrazol-5-yl)-4'-methyl-[1,1'-biphenyl]-4-yl}ethan-1-one
  参考文献：
  名称：

  Carboxylate-assisted ruthenium(II)-catalyzed C–H arylations of 5-aryl tetrazoles: step-economical access to Valsartan

  摘要：

  Carboxylate assistance was key to success for highly efficient ruthenium-catalyzed direct ortho-arylations of tetrazolyl-substituted arenes with aryl halides and triflates in the absence of phosphine ligands. Thus, ruthenium(II) biscarboxylates allowed for C-H bond functionalizations with excellent chemo- and site-selectivities, which set the stage for an atom- and step-economical access to key angiotensin-II-receptor blockers. Mechanistic studies revealed the C-H bond metalation to be reversible, and were suggestive of a rate-determining reductive elimination. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.006

文献信息

• 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。