2-(1-金刚烷基)四唑 | 103408-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(1-金刚烷基)四唑
• 英文名称: 2-(adamantan-1-yl)-2H-tetrazole
• 英文别名: 2-(1-adamantyl)tetrazole；2-(1-adamantyl)-1,2,3,4-tetrazole
• CAS: 103408-87-3
• 化学式: C₁₁H₁₆N₄
• mdl: MFCD02632571
• 分子量: 204.275
• InChiKey: WMSFTGQGTAXLND-UHFFFAOYSA-N

物化性质

• 熔点：
  102-105 °C
• 沸点：
  340.1±25.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.909
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-金刚烷基)四唑 以 硫酸 为溶剂， 反应 24.0h， 生成 1-((3s,5s,7s)-adamantan-1-yl)-1H-tetrazole
  参考文献：
  名称：

  Saraev; Golod, Russian Journal of Organic Chemistry, 1997, vol. 33, # 4, p. 571 - 574

  摘要：

  DOI：
• 作为产物：
  描述：

  四氮唑 、 1-金刚烷醇 在 硫酸 作用下， 生成 2-(1-金刚烷基)四唑
  参考文献：
  名称：

  Saraev; Gavrilov; Golod, Russian Journal of Organic Chemistry, 1999, vol. 35, # 7, p. 1069 - 1072

  摘要：

  DOI：

文献信息

• 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.
• Synthesis and anti-viral activity of azolo-adamantanes against influenza A virus
  作者：Vladimir V. Zarubaev、Efim L. Golod、Pavel M. Anfimov、Anna A. Shtro、Victor V. Saraev、Alexey S. Gavrilov、Alexander V. Logvinov、Oleg I. Kiselev

  DOI：10.1016/j.bmc.2009.11.047

  日期：2010.1

  Chemotherapy and chemoprophylaxis of influenza is one of the most important directions of health protection activity. Due to the high rate of drug-resistant strains of influenza virus, there is a need for the search and further development of new potent antivirals against influenza with a broad spectrum of activity. In the present study, a set of di-, tri- and tetrazole derivatives of adamantane was efficiently prepared and their anti-influenza activities evaluated against rimantadine-resistant strain A/Puerto Rico/8/34. In general, derivatives of tetrazole possessed the highest virus-inhibiting activity. We demonstrated that several compounds of this set exhibited much higher activity than the currently used antiviral rimantadine, a compound of related structure. Moreover, we showed that these azolo-adamantanes were significantly less toxic. This study demonstrates that influenza viruses can be inhibited by adamantylazoles and thus have potential for developing antiviral agents with an alternate mechanism of action. (C) 2009 Elsevier Ltd. All rights reserved.
• Gonzalez; Alarcon; Cabildo, European Journal of Medicinal Chemistry, 1985, vol. 20, # 4, p. 359 - 362
  作者：Gonzalez、Alarcon、Cabildo、et al.

  DOI：——

  日期：——
• GONZALEZ, M. E.;ALARCON, B.;CABILDO, P.;CLARAMUNT, R. M.;SANZ, D.;ELGUERO+, EUR. J. MED. CHEM., 1985, 20, N 4, 359-362
  作者：GONZALEZ, M. E.、ALARCON, B.、CABILDO, P.、CLARAMUNT, R. M.、SANZ, D.、ELGUERO+

  DOI：——

  日期：——
• Change of the Load State of Mhc Molecules
  申请人：Falk Kirsten

  公开号：US20070280957A1

  公开（公告）日：2007-12-06

  The present invention relates to methods for changing the load state of MHC molecules with ligands, the change in the load state being catalysed by a compound of formulae I, IA, II, III or IV1 to IV3. The invention relates further to the use of compounds of formulae I, IA, II, III or IV1 to IV3 or to the use of MHC molecules loaded with ligands, which molecules can be prepared by a method according to the invention, for the treatment of disorders or conditions that are associated with various pathologically excessive or absent immune responses and also for triggering tumour-specific, pathogen-specific or autoreactive immune responses. The invention additionally relates to the use of such compounds for the treatment and diagnosis of cancer, infectious diseases, autoimmune diseases and for attenuating aggressive immune reactions, as well as to the preparation of a vaccine or of a pharmaceutical composition for the treatment of the mentioned disorders or conditions.