2-Isobutyl-2-adamantanol | 14648-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Isobutyl-2-adamantanol
• 英文别名: 2-(2-methylpropyl)adamantan-2-ol
• CAS: 14648-58-9
• 化学式: C₁₄H₂₄O
• 分子量: 208.344
• InChiKey: ALXGUIIGZLCLNY-UHFFFAOYSA-N

物化性质

• 熔点：
  57.0-57.3 °C
• 沸点：
  284.3±8.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)
• 保留指数：
  1570;1588;1602;1618

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Isobutyl-2-adamantanol 在 碘 作用下， 以 xylene 为溶剂， 生成 2-isobutylidene-adamantane
  参考文献：
  名称：

  Kostikov,R.R. et al., Journal of Organic Chemistry USSR (English Translation), 1979, vol. 15, p. 287 - 291

  摘要：

  DOI：
• 作为产物：
  描述：

  金刚烷酮 、 (2-methylpropyl)lithium 在 氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 2.0h， 以85%的产率得到2-Isobutyl-2-adamantanol
  参考文献：
  名称：

  Aminoadamantanes with Persistent in Vitro Efficacy against H1N1 (2009) Influenza A

  摘要：

  A series of 2-adamantanamines with alkyl adducts of various lengths were examined for efficacy against strains of influenza A including those having an S31N mutation in M2 proton channel that confer resistance to amantadine and rimantadine. The addition of as little as one CH2 group to the methyl adduct of the amantadine/rimantadine analogue, 2-methyl-2-aminoadamantane, led to activity in vitro against two M2 S31N viruses A/Calif/07/2009 (H1N1) and A/PR/8/34 (H1N1) but not to a third A/WS/33 (H1N1). Solid state NMR of the transmembrane domain (TMD) with a site mutation corresponding to S31N shows evidence of drug binding. But electrophysiology using the full length S31N M2 protein in HEK cells showed no blockade. A wild type strain, A/Hong Kong/1/68 (H3N2) developed resistance to representative drugs within one passage with mutations in M2 TMD, but A/Calif/07/2009 S31N was slow (>8 passages) to develop resistance in vitro, and the resistant virus had no mutations in M2 TMD. The results indicate that 2-alkyl-2-aminoadamantane derivatives with sufficient adducts can persistently block p2009 influenza A in vitro through an alternative mechanism. The observations of an HA1 mutation, N160D, near the sialic acid binding site in both 6-resistant A/Calif/07/2009(H1N1) and the broadly resistant A/WS/33(H1N1) and of an HA1 mutation, I325S, in the 6-resistant virus at a cell-culture stable site suggest that the drugs tested here may block infection by direct binding near these critical sites for virus entry to the host cell.

  DOI：

  10.1021/jm500598u

文献信息

• Aliphatic Radical Relay Heck Reaction at Unactivated C(sp ³ )−H Sites of Alcohols
  作者：Padon Chuentragool、Dongari Yadagiri、Taiki Morita、Sumon Sarkar、Marvin Parasram、Yang Wang、Vladimir Gevorgyan

  DOI：10.1002/anie.201812398

  日期：2019.2.4

  aliphatic alcohols at unactivated β-, γ-, and δ-C(sp3 )-H sites. The use of an easily installed/removed Si-based auxiliary enables selective I-atom/radical translocation events at remote C-H sites followed by the Heck reaction. Notably, the reaction proceeds smoothly under mild visible-light-mediated conditions at room temperature, producing highly modifiable and valuable alkenol products from readily available

  Mizoroki-Heck反应是使芳基，乙烯基和烷基卤化物进行烯基化的最有效方法之一。鉴于其固有的性质，该方案要求使用在官能化位点具有卤素原子的化合物。但是，在脂族体系中特定位置具有卤原子的有机分子的可及性受到极大限制。因此，期望允许Heck反应在特定的未官能化的C（sp3）-H位点发生的方案。此处报道的是一种自由基中继Heck反应，该反应允许脂族醇在未活化的β-，γ-和δ-C（sp3）-H位点进行选择性的远程烯基化。使用易于安装/拆卸的硅基助剂可以在遥远的CH位点进行选择性的I原子/自由基易位事件，然后发生Heck反应。尤其，
• Indole derivatives and their use in neurodegenerative diseases
  申请人：Merck Patent GmbH

  公开号：US10676433B2

  公开（公告）日：2020-06-09

  The present invention relates to indole compounds, and pharmaceutically acceptable compositions thereof, useful as antagonists of P2X7, and for the treatment of P2X7-related disorders.

  本发明涉及作为 P2X7 拮抗剂和用于治疗 P2X7 相关疾病的吲哚化合物及其药学上可接受的组合物。
• Solvation and steric effects on electrophilic reactivity of ethylenic compounds. 1. Stereochemistry and bromination of congested adamantylidenealkanes
  作者：Marie Francoise Ruasse、Shahrokh Motallebi、Bernard Galland、John S. Lomas

  DOI：10.1021/jo00295a013

  日期：1990.4
• NOVEL INDOLE DERIVATIVES AND THEIR USE IN NEURODEGENERATIVE DISEASES
  申请人：Merck Patent GmbH

  公开号：US20190161447A1

  公开（公告）日：2019-05-30

  The present invention relates to indole compounds, and pharmaceutically acceptable compositions thereof, useful as antagonists of P2X7, and for the treatment of P2X7-related disorders.
• Kostikov,R.R. et al., Journal of Organic Chemistry USSR (English Translation), 1979, vol. 15, p. 287 - 291
  作者：Kostikov,R.R. et al.

  DOI：——

  日期：——