2-Phenyl-5-hydroxymethyltetrazol | 55408-42-9

• 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-Phenyl-5-hydroxymethyltetrazol
• 英文别名: 2-Phenyl-5-(hydroxymethyl)tetrazole；(2-phenyltetrazol-5-yl)methanol
• CAS: 55408-42-9
• 化学式: C₈H₈N₄O
• 分子量: 176.178
• InChiKey: XJGBSOQQXSCHDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Phenyl-5-hydroxymethyltetrazol 在 吡啶-2-磺酰氟 、 7-甲基-1,5,7-三氮杂二环[4.4.0]癸-5-烯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以72%的产率得到5-(fluoromethyl)-2-phenyl-2H-tetrazole
  参考文献：
  名称：

  Regioselective synthesis of carboxylic and fluoromethyl tetrazoles enabled by silver-catalyzed cycloaddition of diazoacetates and aryl diazonium salts

  摘要：

  Here we present a dipolar [3 + 2] cycloaddition transformation of diazoacetates with arenediazonium salts under silver catalysis, thus offering a straightforward approach for the regioselective construction of carboxylic tetrazoles. Several merits are accompanied with this reaction including readily available starting reagents, broad coupling scope, high yields, and friendly reaction conditions. The synthetic value is further showcased by one-pot conversion of commercially available primary arylamines to tetrazoles and successful transformations of the cycloadducts into valuable 5-fluoromethyltetrazoles and an analogue of P2X3 receptor antagonist. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131063
• 作为产物：
  描述：

  benzenediazonium tetrafluoroborate 在 silver(I) acetate 、 二异丁基氢化铝 、 sodium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.17h， 生成 2-Phenyl-5-hydroxymethyltetrazol
  参考文献：
  名称：

  Regioselective synthesis of carboxylic and fluoromethyl tetrazoles enabled by silver-catalyzed cycloaddition of diazoacetates and aryl diazonium salts

  摘要：

  Here we present a dipolar [3 + 2] cycloaddition transformation of diazoacetates with arenediazonium salts under silver catalysis, thus offering a straightforward approach for the regioselective construction of carboxylic tetrazoles. Several merits are accompanied with this reaction including readily available starting reagents, broad coupling scope, high yields, and friendly reaction conditions. The synthetic value is further showcased by one-pot conversion of commercially available primary arylamines to tetrazoles and successful transformations of the cycloadducts into valuable 5-fluoromethyltetrazoles and an analogue of P2X3 receptor antagonist. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131063

文献信息

• Synthesis and Evaluation of Photoreactive Tetrazole Amino Acids
  作者：Yizhong Wang、Qing Lin

  DOI：10.1021/ol901300h

  日期：2009.8.20

  Six photoreactive tetrazole amino acids were efficiently synthesized either by the de novo Kakehi tetrazole synthesis method or by alkylation of a glycine Schiff base with tetrazole-containing alkyl halides, and four of them showed excellent reactivity toward a simple alkene in the photoinduced 1,3-dipolar cycloaddition reaction in acetonitrile/PBS buffer (1:1) mixture.

  通过从头 Kakehi 四唑合成方法或通过甘氨酸席夫碱与含四唑的烷基卤化物的烷基化，有效地合成了六种光反应性四唑氨基酸，其中四种对光诱导的 1,3- 中的简单烯烃表现出优异的反应性。在乙腈/PBS 缓冲液 (1:1) 混合物中进行偶极环加成反应。
• HETEROCYCLIC M-GLU5 ANTAGONISTS
  申请人：Leonardi Amedeo

  公开号：US20120028931A1

  公开（公告）日：2012-02-02

  Compounds I (R 1 is an optionally substituted C 1 -C 13 heteromonocyclic, heterobicyclic or heterotricyclic group containing from 1 to 5 heteroatoms selected from N, O and S; R 2 is H, an optionally substituted monocyclic aromatic group, or a C 1 -C 5 heteroaromatic group containing from 1 to 4 heteroatoms selected from N, O and S; R 3 is an optionally substituted C 1 -C 13 heteromonocyclic, heterobicyclic or heterotricyclic group containing from 1 to 5 heteroatoms selected from N, O and S; an optionally substituted mono-, bi- or tricyclic C 6 -C 14 aryl group, an optionally substituted C 3 -C 6 cycloalkyl group, or an optionally substituted C 3 -C 6 cycloalkenyl group; each R 4 , independently for each position capable of substitution, is H or C 1 -C 6 alkyl; R 5 is H, halogen or C 1 -C 6 alkyl; m is 0, 1 or 2; n is 0, 1 or 2; p is 0, 1, 2, 3, 4, 5, or 6; and is an optional double bond) and their enantiomers, diastereomers, N-oxides and pharmaceutically acceptable salts, and pharmaceutical compositions containing them, are useful for the treatment of neuromuscular dysfunction of the lower urinary tract and also for the treatment of gastrooesophageal reflux disease; anxiety disorder; abuse, substance dependence and substance withdrawal disorders; neuropathic pain disorder, migraine and fragile X syndrome disorders.

  化合物I（其中R1是可选取代的C1-C13杂环单环、杂环双环或杂环三环基团，包含1-5个从N、O和S中选取的杂原子；R2是H、可选取代的单环芳香基团，或包含1-4个从N、O和S中选取的杂原子的C1-C5杂环芳香基团；R3是可选取代的C1-C13杂环单环、杂环双环或杂环三环基团，包含1-5个从N、O和S中选取的杂原子；可选取代的单环、双环或三环C6-C14芳基基团，可选取代的C3-C6环烷基基团或可选取代的C3-C6环烯基基团；每个R4，在可取代的每个位置上，独立地是H或C1-C6烷基；R5是H、卤素或C1-C6烷基；m为0、1或2；n为0、1或2；p为0、1、2、3、4、5或6；并且是可选的双键），它们的对映异构体、顺反异构体、N-氧化物和药学上可接受的盐，以及含有它们的制药组合物，对于治疗下泌尿道神经肌肉功能障碍和胃食管反流病，焦虑症、滥用、物质依赖和物质戒断障碍，神经病性疼痛障碍、偏头痛和脆性X综合症障碍有用。
• Synthesis and Structure−activity Relationships of Antitubercular 2-Nitroimidazooxazines Bearing Heterocyclic Side Chains
  作者：Hamish S. Sutherland、Adrian Blaser、Iveta Kmentova、Scott G. Franzblau、Baojie Wan、Yuehong Wang、Zhenkun Ma、Brian D. Palmer、William A. Denny、Andrew M. Thompson

  DOI：10.1021/jm901378u

  日期：2010.1.28

  Recently described biphenyl analogues Of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more efficacious than the parent drug in a mouse model of acute M. tb infection, and one displayed a 2-fold higher solubility.
• LIPPMANN E.; KOENNECKE A.; BEYER G., MONATSH. CHEM. <MOCH-AP>, 1975, 106, NO 2, 437-442
  作者：LIPPMANN E.、 KOENNECKE A.、 BEYER G.

  DOI：——

  日期：——
• LIPPMANN E.; KOENNECKE A.; BEYER G., MONATSH. CHEM. <MOCH-AP>, 1975, 106, NO 2, 443-449
  作者：LIPPMANN E.、 KOENNECKE A.、 BEYER G.

  DOI：——

  日期：——