3-isothiocyanatoadamantan-1-ol | 130837-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-isothiocyanatoadamantan-1-ol
• CAS: 130837-41-1
• 化学式: C₁₁H₁₅NOS
• 分子量: 209.312
• InChiKey: BDOVZNVLJFTWKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  64.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-isothiocyanatoadamantan-1-ol 在 sodium azide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 以39%的产率得到1-(3-hydroxy-1-adamantyl)-1,4-dihydrotetrazol-5-thione
  参考文献：
  名称：

  Synthesis and anti-viral activity of azolo-adamantanes against influenza A virus

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.11.047
• 作为产物：
  描述：

  异硫氰酸1-金刚烷酯 在 硝酸铵 、 硫酸 作用下， 以88%的产率得到3-isothiocyanatoadamantan-1-ol
  参考文献：
  名称：

  Synthesis and anti-viral activity of azolo-adamantanes against influenza A virus

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.11.047

文献信息

• Preparation of 1,3-Functionalized Adamantanes by the Lewis Acid Catalyzed Electrophilic Cyclization of 7-Methylenebicyclo[3.3.1]nonan-3-one in the Presence of π- and<i>N</i>-Nucleophiles
  作者：George A. Olah、Ramesh Krishnamurti、G. K. Surya Prakash

  DOI：10.1055/s-1990-26967

  日期：——

  Preparation of 1,3-difunctionalized adamantane derivatives from 7-methylenebicyclo[3.3.1] nonane-3-one (1) in the presence of nucleophiles under Lewis acid catalysis is described. Reaction of 1 with benzene using a variety of Lewis acid catalysts gave 1,3-diphenyladamantane (4) as the major product. Trimethylsilyl cyanide and azide efficiently reacted with 1 in the presence of zinc iodide as the catalyst to give good yields of the corresponding 3-trimethylsiloxyadamantyl isocyanide and azide, respectively. Trimethylsilyl isothiocyanate gave a 1:1 mixture of the thiocyanate and isothiocyanate derivatives. Silyl enol ethers, such as those of acetophenone and cyclopentanone, and allyltrimethylsilane also reacted with 1 to afford the corresponding 1,3-difunctionalized adamantanes.

  介绍了在路易斯酸催化下，由 7-亚甲基双环[3.3.1]壬烷-3-酮（1）在亲核剂存在下制备 1,3-二官能化金刚烷衍生物的过程。 在多种路易斯酸催化剂的作用下，1 与苯反应得到的主要产物是 1,3-二苯基金刚烷（4）。在碘化锌作为催化剂的情况下，三甲基硅基氰化物和叠氮化物能有效地与 1 反应，分别得到相应的 3-三甲基硅氧基金刚烷异氰酸酯和叠氮化物，收率很高。异硫氰酸三甲基硅酯可得到硫氰酸盐和异硫氰酸盐衍生物 1:1 的混合物。硅烯醇醚（如苯乙酮和环戊酮的硅烯醇醚）和烯丙基三甲基硅烷也能与 1 反应，生成相应的 1,3-二官能化金刚烷。
• OLAH, GEORGE A.;KRISHNAMURTI, RAMESH;PRAKASH, G. K. SURYA, SYNTHESIS,(1990) N, C. 646-648
  作者：OLAH, GEORGE A.、KRISHNAMURTI, RAMESH、PRAKASH, G. K. SURYA

  DOI：——

  日期：——
• 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.