2-(adamantan-1-yl)-5-phenyl-2H-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: 2-(adamantan-1-yl)-5-phenyl-2H-tetrazole
• 英文别名: 2-(1-adamantyl)-5-phenyltetrazole
• 化学式: C₁₇H₂₀N₄
• 分子量: 280.373
• InChiKey: LINSLAJXFUEMGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲腈 在 sodium azide 、 硫酸 、 盐酸二甲胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.67h， 生成 2-(adamantan-1-yl)-5-phenyl-2H-tetrazole
  参考文献：
  名称：

  2-（金刚烷-1-基）-5-芳基-1,3,4-恶二唑和2-（金刚烷-1-基）-5-芳基四唑的合成，结构和抗流感活性

  摘要：

  多氮杂环的两个新系列金刚烷基衍生物：2-（金刚烷-1-基）-5-芳基-1,3,4-恶二唑和2-（金刚烷-1-基）-5-芳基-2 H-四唑，已经合成，并且它们的结构已经通过NMR光谱，质谱和X射线分析确定。体外生物学研究表明，某些合成的2-（金刚烷-1-基）-5-芳基-2 H-四唑对H1N1甲型流感病毒具有很高的抑制活性，同时选择性相对较低。

  DOI：

  10.1134/s107042801804019x

文献信息

• Alkylation of 5-Substituted 1<i>H</i>-Tetrazoles via the Diazotization of Aliphatic Amines
  作者：Guillaume Reynard、Hélène Lebel

  DOI：10.1021/acs.joc.1c01585

  日期：2021.9.3

  A new alkylation reaction of monosubstituted tetrazoles via the diazotization of aliphatic amines is reported. This method enables preferential formation of 2,5-disubstituted tetrazoles. A one-pot 1,3-dipolar cycloaddition/diazotization sequence starting from widely available nitriles is also described. Azide residues are quenched in the second step with the nitrite reagent, thus limiting the intrinsic

  报道了通过脂肪胺的重氮化作用进行单取代四唑的新烷基化反应。这种方法能够优先形成 2,5-二取代四唑。还描述了从广泛可用的腈开始的一锅 1,3-偶极环加成/重氮化序列。叠氮化物残留物在第二步中用亚硝酸盐试剂淬灭，从而限制了与三甲基甲硅烷基叠氮化物相关的内在风险。反应条件与几个官能团相容，包括硫氰酸酯，它们优先提供双取代的 2-烷基-5-（取代-硫代）四唑。
• Bu₄NI-Catalyzed, Radical-Induced Regioselective <i>N</i>-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters
  作者：Suresh Rajamanickam、Chitranjan Sah、Bilal Ahmad Mir、Subhendu Ghosh、Garima Sethi、Vinita Yadav、Sugumar Venkataramani、Bhisma K. Patel

  DOI：10.1021/acs.joc.9b02875

  日期：2020.2.21

  using tert-butyl hydroperoxide (TBHP) as the methyl source, alkyl diacyl peroxides as the primary alkyl source, alkyl peresters as the secondary and tertiary alkyl sources, and aryl diacyl peroxides as the arylating source. These reactions proceed without pre-functionalization of tetrazole and in the absence of any metal catalysts. Here, peroxides serve the dual role of oxidants as well as alkylating or

  使用叔丁基过氧化氢（TBHP）作为甲基源，烷基二酰基过氧化物作为主要烷基源，烷基过酸酯作为仲和叔基，已经实现了Bu4NI催化的四唑的区域选择性N2-甲基化，N2-烷基化和N2-芳基化烷基来源和芳基二酰基过氧化物作为芳基化来源。这些反应在没有四唑的预官能化和没有任何金属催化剂的情况下进行。在此，过氧化物起到氧化剂以及烷基化或芳基化剂的双重作用。根据DFT计算，发现自旋密度，过渡态势垒（动力学控制）和产物的热力学稳定性（热力学控制）在N-烷基化过程中观察到的区域选择性中起着至关重要的作用。
• Alkylation of 5-Substituted Tetrazoles with Various Alcohols in 1,2-Dichloroethane in the Presence of BF3·Et2O
  作者：S. A. Egorov、M. A. Ishchenko、Ya. V. Prokopovich、V. I. Ivanova

  DOI：10.1134/s107042802007012x

  日期：2020.7

  The alkylation of 1H-tetrazole, 5-methyl-1H-tetrazole, and 5-phenyl-1H-tetrazole with primary, secondary, and tertiary alcohols, including benzylic and allylic ones, have been studied in 1,2-dichloroethane in the presence of boron trifluoride-diethyl ether complex. Neither primary nor secondary saturated alcohols alkylated tetrazoles in the given system. Tertiary alcohols suchtert-butyl alcohol and adamantan-1-ol reacted with unsubstituted and 5-substituted tetrazoles to give 70-85% of the corresponding 2-alkyl-5-R-tetrazoles with high regioselectivity. The alkylation of 1H-tetrazole with benzyl alcohol afforded 55% of 2-benzyl-2H-tetrazole as the only product. The alkylation of 1H-tetrazole with various allylic alcohols led to the formation of mixtures of 2-alkyl-2H-tetrazoles with isomeric alkyl substituents.
• Saraev; Gavrilov; Golod, Russian Journal of Organic Chemistry, 1999, vol. 35, # 7, p. 1069 - 1072
  作者：Saraev、Gavrilov、Golod

  DOI：——

  日期：——
• Synthesis, Structure, and Anti-influenza Activity of 2-(Adamantan-1-yl)-5-aryl-1,3,4-oxadiazoles and 2-(Adamantan-1-yl)-5-aryltetrazoles
  作者：D. V. Seliverstova、V. V. Suslonov、V. V. Zarubaev、R. E. Trifonov

  DOI：10.1134/s107042801804019x

  日期：2018.4

  heterocycles, 2-(adamantan-1-yl)-5-aryl- 1,3,4-oxadiazoles and 2-(adamantan-1-yl)-5-aryl-2H-tetrazoles, have been synthesized, and their structure has been determined by NMR spectroscopy, mass spectrometry, and X-ray analysis. Biological studies in vitro have revealed high inhibitory activity of some of the synthesized 2-(adamantan-1-yl)-5-aryl-2H-tetrazoles against H1N1 influenza A viruses in combination

  多氮杂环的两个新系列金刚烷基衍生物：2-（金刚烷-1-基）-5-芳基-1,3,4-恶二唑和2-（金刚烷-1-基）-5-芳基-2 H-四唑，已经合成，并且它们的结构已经通过NMR光谱，质谱和X射线分析确定。体外生物学研究表明，某些合成的2-（金刚烷-1-基）-5-芳基-2 H-四唑对H1N1甲型流感病毒具有很高的抑制活性，同时选择性相对较低。