(1l,3x,5u,7x)-7-(hydroxymethyl)bicyclo<3.3.1>nonan-3-ol | 66674-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1l,3x,5u,7x)-7-(hydroxymethyl)bicyclo<3.3.1>nonan-3-ol
• 英文别名: 7-(Hydroxymethyl)bicyclo<3.3.1>nonan-3-ol；[7-(hydroxymethyl)bicyclo[3.3.1]nonan-3-ol]；7-(hydroxymethyl)bicyclo[3.3.1]nonan-3-ol
• CAS: 66674-81-5
• 化学式: C₁₀H₁₈O₂
• mdl: MFCD00563053
• 分子量: 170.252
• InChiKey: LTHDKLTZLLXHMT-UHFFFAOYSA-N

物化性质

• 熔点：
  170-174 °C
• 沸点：
  316.4±10.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• 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：

  (1l,3x,5u,7x)-7-(hydroxymethyl)bicyclo<3.3.1>nonan-3-ol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 66.0h， 以1.088 g的产率得到二环[3.3.1]壬-3,7-二酮
  参考文献：
  名称：

  N-Arylalkyl-2-azaadamantanes as cage-expanded polycarbocyclic sigma (σ) receptor ligands

  摘要：

  A series of racemic N-arylalkyl-2-azaadamantan-1-ols (9-15) and the corresponding deoxygenated, achiral N-arylalkyl-2-azaadamantanes (23-29) were synthesized and screened in competition binding assays against a panel of CNS targets. Adamantyl hemiaminals 9-15 displayed generally low affinity for both sigma(1) (K-i values = 294-1950 nM) and sigma(2) receptors (K-i values = 201-1020 nM), and negligible affinity for 42 other CNS proteins. Deoxygenation of 9-15 to give the corresponding achiral azaadamantanes 23-29 greatly improved affinity for sigma(1) (K-i values = 8.3-239 nM) and sigma(2) receptors (K-i values = 34-312 nM). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.028
• 作为产物：
  描述：

  金刚烷 在 sodium hydroxide 、 aluminum tri-bromide 、 三氟化硼四氢呋喃络合物 、 双氧水 、 溴 、 三溴化硼 作用下， 以 1,4-二氧六环 为溶剂， 反应 21.58h， 生成 (1l,3x,5u,7x)-7-(hydroxymethyl)bicyclo<3.3.1>nonan-3-ol
  参考文献：
  名称：

  羟醛缩合中过渡态几何学的研究。

  摘要：

  已经研究了模型化合物以阐明醇醛反应中烯醇化物和羰基部分的相对取向。这些化合物的合成是由源自金刚烷碎裂的常见前体实现的。限制过渡结构的模型表明，环化必须通过醛相对于烯醇化物的向斜或反周向取向进行。讨论了选择性的起源以及烯醇和过渡结构的含义

  DOI：

  10.1021/ja00006a042

文献信息

• A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor
  作者：Dmitry A. Vasilenko、Kirill S. Sadovnikov、Kseniya N. Sedenkova、Dmitry S. Karlov、Eugene V. Radchenko、Yuri K. Grishin、Victor B. Rybakov、Tamara S. Kuznetsova、Vladimir L. Zamoyski、Vladimir V. Grigoriev、Vladimir A. Palyulin、Elena B. Averina

  DOI：10.3390/molecules26216411

  日期：——

  convenient synthetic approach to novel functionalized bis(isoxazoles), the promising bivalent ligands of the AMPA receptor, was elaborated. It was based on the heterocyclization reactions of readily available electrophilic alkenes with the tetranitromethane-triethylamine complex. The structural diversity of the synthesized compounds was demonstrated. In the electrophysiological experiments using the patch

  详细阐述了一种新型功能化双（异恶唑）（AMPA 受体的有前途的二价配体）的便捷合成方法。它基于易于获得的亲电烯烃与四硝基甲烷-三乙胺络合物的杂环化反应。证明了合成化合物的结构多样性。在浦肯野神经元上使用膜片钳技术的电生理实验中，化合物 1,4-苯二（亚甲基）双（5-氨基异恶唑-3-羧酸盐）被证明是高效的 AMPA 受体正调节剂，增强红藻氨酸诱导的10 -11 M 时电流高达 70% 。
• [EN] CONFORMATIONALLY CONSTRAINED PACLITAXEL ANALOGS AND THEIR USE AS ANTICANCER AND ANTI-ALZHEIMERS AGENTS<br/>[FR] ANALOGUES DE PACLITAXEL A CONTRAINTES CONFORMATIONNELLES ET LEUR UTILISATION EN TANT QU'AGENTS ANTICANCEREUX ET ANTI-ALZHEIMER
  申请人：VIRGINIA TECH INTELL PROP

  公开号：WO2005070414A1

  公开（公告）日：2005-08-04

  Constrained paclitaxel derivatives include a bridge extending from the C-3’ phenyl to either the C4 or -3 positions. Many of the constrained paclitaxel derivatives provide activity comparable or superior to the natural product paclitaxel.

  受限紫杉醇衍生物包括从C-3'苯基延伸到C4或-3位置的桥。许多受限紫杉醇衍生物提供与天然产物紫杉醇相媲美或更优越的活性。
• Adamantane amine-linked chloroquinoline derivatives as chloroquine resistance modulating agents in Plasmodium falciparum
  作者：Opute M. Yvette、Sarel F. Malan、Dale Taylor、Erika Kapp、Jacques Joubert

  DOI：10.1016/j.bmcl.2018.03.026

  日期：2018.5

  Previously we have shown that pentacycloundecylamine- chloroquinoline (PCU-CQ) conjugates possess significant chemosensitizing abilities and can circumvent the resistance associated with chloroquine (CQ) resistant plasmodia. In order to further explore structurally related polycyclic compounds as reversed CQ agents we synthesized a series of eight aza-adamantanol (1-4) and adamantane-imine (5-8) CQ conjugates. All conjugates showed limited cytotoxicity against CHO cells (IC50 > 37 mM). Compounds 1, 2 and 5 were highly active (K1 IC50 < 100 nM) exhibiting a 3-4- fold increase in antiplasmodial activity against CQ resistant strain K1 compared to CQ. Reduced cross-resistance (resistance index, RI: 2-4.3) relative to CQ (RI = 38) was also observed for these compounds. Compound 1 which showed an 18-fold enhancement at retaining its activity against the K1 strain compared to CQ is a promising candidate to substitute CQ in P. falciparum resistant malaria. (C) 2018 Elsevier Ltd. All rights reserved.
• Oxidation of 7-(hydroxymethyl)bicyclo[3.3.1]nonan-3-ol. Convenient synthesis of bicyclo[3.3.1]nonane-3,7-dione
  作者：Julie A. Zalikowski、Kevin E. Gilbert、Weston Thatcher Borden

  DOI：10.1021/jo01290a029

  日期：1980.1
• ZALIKOWSKI J. A.; GILBERT K. E.; BORDEN W. T., J. ORG. CHEM., 1980, 45, NO 2, 346-347
  作者：ZALIKOWSKI J. A.、 GILBERT K. E.、 BORDEN W. T.

  DOI：——

  日期：——