2-hydroxy-1-adamantanomethanol | 59182-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-1-adamantanomethanol
• 英文别名: 2-hydroxy-1-adamantane methanol；1-Hydroxymethyl-2-adamantanol；2-Hydroxy-1-adamantylmethanol；1-(Hydroxymethyl)adamantan-2-ol
• CAS: 59182-38-6
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: PUFOBDWCLXCAPH-UHFFFAOYSA-N

物化性质

• 沸点：
  331.8±10.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-1-adamantanomethanol 在 chromium(VI) oxide 、 硫酸 作用下， 生成 1-Carbamoyladamantan-2-on
  参考文献：
  名称：

  Solvolysis of 1-substituted-2-adamantyl sulfonates. Bridging or no bridging?

  摘要：

  DOI：

  10.1021/ja00433a041
• 作为产物：
  描述：

  4-(epoxymethylene)protoadamantane 在 硫酸 作用下， 以 丙酮 为溶剂， 生成 2-hydroxy-1-adamantanomethanol
  参考文献：
  名称：

  Solvolysis of 1-substituted-2-adamantyl sulfonates. Bridging or no bridging?

  摘要：

  DOI：

  10.1021/ja00433a041

文献信息

• APOPTOSIS-INDUCED AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES
  申请人：AbbVie Inc.

  公开号：US20130096120A1

  公开（公告）日：2013-04-18

  Disclosed are compounds which inhibit the activity of anti-apoptotic Bcl-xL proteins, compositions containing the compounds and methods of treating diseases during which is expressed anti-apoptotic Bcl-xL protein.

  揭示了抑制抗凋亡Bcl-xL蛋白活性的化合物，含有这些化合物的组合物以及治疗在其中表达抗凋亡Bcl-xL蛋白的疾病的方法。
• Synthesis of 1,2-annulated adamantane heterocycles: structural determination studies of a bioactive cyclic sulfite
  作者：Grigoris Zoidis、Dimitra Benaki、Vassilios Myrianthopoulos、Lieve Naesens、Erik De Clercq、Emmanuel Mikros、Nicolas Kolocouris

  DOI：10.1016/j.tetlet.2009.03.132

  日期：2009.6

  The novel heterocycle 3-oxatetracyclo[5.3.1.15,9.02,5]dodecane 4 is prepared by a simple and effective method, involving synthesis of the corresponding 2-hydroxy-1-adamantanomethanol followed by its intramolecular cyclization with thionyl chloride, along with 4-oxo-adamantane-3,5,4-dioxathiane 5 in yields depending on the reaction temperature. Dioxathiane 5 was markedly active against vesicular stomatitis

  新颖的杂环3-氧杂四环[5.3.1.1 5,9 0.0 2,5 ]十二烷4是通过一个简单而有效的方法制备，涉及相应的2-羟基-1- adamantanomethanol的合成，随后其分子内环化与亚硫酰氯取决于反应温度，其产率与4-氧代金刚烷-3,5,4-二氧杂环丁烷5的产率有关。Dioxathiane 5对水疱性口炎病毒具有显着活性，其效力比（S）-9-（2,3-二羟丙基）腺嘌呤高2.5倍。NMR数据和有关亚硫酸盐5和相应的二恶烷6的理论计算表明，SO是赤道取向的。
• APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES
  申请人：AbbVie Inc.

  公开号：US20150072978A1

  公开（公告）日：2015-03-12

  Disclosed are compounds which inhibit the activity of anti-apoptotic Bcl-xL proteins, compositions containing the compounds and methods of treating diseases during which is expressed anti-apoptotic Bcl-xL protein.

  本发明涉及抑制抗凋亡Bcl-xL蛋白活性的化合物、含有该化合物的组合物以及治疗表达抗凋亡Bcl-xL蛋白相关疾病的方法。
• Chakrabarti,J.K. et al., Journal of the Chemical Society. Perkin transactions I, 1976, p. 1893 - 1900
  作者：Chakrabarti,J.K. et al.

  DOI：——

  日期：——
• Design and synthesis of 1,2-annulated adamantane piperidines with anti-influenza virus activity
  作者：Grigoris Zoidis、Nicolas Kolocouris、Lieve Naesens、Erik De Clercq

  DOI：10.1016/j.bmc.2009.01.009

  日期：2009.2

  1-2 Annulated adamantane piperidines 4, 6, 16, 17, 19, 23 and 25 were synthesized and evaluated for anti-influenza A virus activity. The stereoelectronic requirements for optimal antiviral potency were investigated. Piperidine 23 proved to be the most active of the compounds tested against influenza A virus, being 3.5-fold more active than amantadine, equipotent to rimantadine and 15-fold more potent than ribavirin. It is noteworthy that piperidine 23 displayed one of the highest selectivity indexes (SI>732) among aminoadamantanes or other cage structure amines tested till now. (c) 2009 Elsevier Ltd. All rights reserved.