5-<4'-Methyl-1,1'-biphenyl-2-yl>-1H-tetrazole-1-propanenitrile | 120568-17-4

• 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: 5-<4'-Methyl-1,1'-biphenyl-2-yl>-1H-tetrazole-1-propanenitrile
• 英文别名: 2-[1-(beta-cyanoethyl)-1-H-tetrazol-5-yl]-4'-methylbiphenyl；3-[5-[2-(4-methylphenyl)phenyl]tetrazol-1-yl]propanenitrile
• CAS: 120568-17-4
• 化学式: C₁₇H₁₅N₅
• 分子量: 289.34
• InChiKey: VIQJDDFWTYRXID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-<4'-Methyl-1,1'-biphenyl-2-yl>-1H-tetrazole-1-propanenitrile 在 N-溴代丁二酰亚胺(NBS) 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 为溶剂， 生成 N-(三苯基甲基)-5-(4'-溴甲基联苯-2-基)四氮唑
  参考文献：
  名称：

  1,(3,)5-substituted imidazoles, useful in the treatment of hypertension and methods for their preparation

  摘要：

  公开号：

  EP2162441B1
• 作为产物：
  描述：

  2-(4-甲基苯基)苯甲酰氯 在 sodium hydroxide 、 五氯化磷 、 dinitrogen tetraoxide 、 肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 四氯化碳 、 乙腈 为溶剂， 反应 14.0h， 生成 5-<4'-Methyl-1,1'-biphenyl-2-yl>-1H-tetrazole-1-propanenitrile
  参考文献：
  名称：

  Three synthetic routes to a sterically hindered tetrazole. A new one-step mild conversion of an amide into a tetrazole

  摘要：

  5-[4'-Methyl-1,1'-biphenyl-2-yl]-1H-tetrazole (6), which contains a sterically hindered o-tetrazole group, was synthesized by three different routes, one of them employing a new tetrazole synthesis. The first involved the reaction of trialkyltin azides with 4'-methyl-1,1'-biphenyl-2-carbonitrile (3). The resultant trimethyltin-tetrazole adduct could be hydrolyzed with acid to yield biphenylytetrazole 6. The tri-n-butyltin-tetrazole adduct, however, was transformed into the corresponding N-trityl-protected tetrazole 5 to permit removal of the organic soluble tri-n-butyltin byproducts. The trityl group also permits 5 to be brominated at the benzylic position and then alkylated by imidazole derivatives. Subsequent acid hydrolysis of the trityl protecting group of 5 yielded biphenylyltetrazole 6. The second synthesis involved the nitrosation of an N-(2-cyanoethyl)-protected biphenylamidrazone 10 using N2O4 (g) to yield N-(2-cyanoethyl)-protected tetrazole 12. Aqueous base removes the cyanoethyl protecting group to yield biphenylyltetrazole 6. The third method involves the novel transformation of an N-(2-cyanoethyl)-substituted amide into the corresponding N-(2-cyanoethyl)-protected tetrazole in one step using triphenylphosphine, diethyl azodicarboxylate (DEAD), and azidotrimethylsilane. Subsequent base hydrolysis of the cyanoethyl group yielded 6 as before. Examples are also provided of the application of this new reaction to other N-(2-cyanoethyl)-protected carboxamides.

  DOI：

  10.1021/jo00007a027

文献信息

• 1,(3,)5-SUBSTITUTED IMIDAZOLES, THEIR USE IN THE TREATMENT OF HYPERTENSION AND METHODS FOR THEIR PREPARATION
  申请人：Matsoukas John

  公开号：US20100166837A1

  公开（公告）日：2010-07-01

  The present invention provides novel 1,5 and 1,3,5-substituted imidazole compounds in hydrophilic or lipophilic form, which are useful as angiotensin II ATI receptor antagonists suitable for transdermal delivery. The invention also provides pharmaceutical compositions containing such compounds, processes and intermediates for preparing compounds and their use in methods of treating hypertension and cardiovascular diseases.

  本发明提供了新颖的1,5和1,3,5-取代咪唑化合物，其以亲水或亲脂形式存在，可用作适合经皮途径给药的血管紧张素II ATI受体拮抗剂。该发明还提供了含有这些化合物的药物组合物，用于制备化合物的方法和中间体，以及它们在治疗高血压和心血管疾病的方法中的应用。
• Tetrazole intermediates to antihypertensive compounds
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04870186A1

  公开（公告）日：1989-09-26

  Tetrazole intermediates useful to prepare antihypertensive compounds described in coassigned application U.S. Ser. No. 884,920, filed July 11, 1986, are described, these tetrazoles have the formula: ##STR1## wherein X.sup.1 and X.sup.2 are as described in the specification.

  本文介绍了用于制备抗高血压化合物的四唑中间体，这些四唑具有以下公式：##STR1## 其中X.sup.1和X.sup.2如规范中所述。
• ALDRICH, PAUL E.;DUNCIA, JOHN JONAS V.;PIERCE, MICHAEL E.
  作者：ALDRICH, PAUL E.、DUNCIA, JOHN JONAS V.、PIERCE, MICHAEL E.

  DOI：——

  日期：——
• DUNCIA, JOHN V.;PIERCE, MICHAEL E.;SANTELLA, JOSEPH B. (III), J. ORG. CHEM., 56,(1991) N, C. 2395-2400
  作者：DUNCIA, JOHN V.、PIERCE, MICHAEL E.、SANTELLA, JOSEPH B. (III)

  DOI：——

  日期：——
• US8563586B2
  申请人：——

  公开号：US8563586B2

  公开（公告）日：2013-10-22