4-(tetrahydrofuran-2-yl)phenol | 66123-44-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(tetrahydrofuran-2-yl)phenol
• 英文别名: 2-(4-hydroxyphenyl)tetrahydrofuran；4-(Oxolan-2-yl)phenol
• CAS: 66123-44-2
• 化学式: C₁₀H₁₂O₂
• mdl: MFCD06655970
• 分子量: 164.204
• InChiKey: IUSPLBQETIEWCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  304.3±35.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(tetrahydrofuran-2-yl)phenol 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 1-[3-[4-(Oxolan-2-yl)phenoxy]propyl]piperidine
  参考文献：
  名称：

  Novel and highly potent histamine H3 receptor ligands. Part 1: withdrawing of hERG activity

  摘要：

  Pre-clinical investigation of some aryl-piperidinyl ether histamine H3 receptor antagonists revealed a strong hERG binding. To overcome this issue, we have developed a QSAR model specially dedicated to H3 receptor ligands. This model was designed to be directly applicable in medicinal chemistry with no need of molecular modeling. The resulting recursive partitioning trees are robust (80-85% accuracy), but also simple and comprehensible. A novel promising lead emerged from our work and the structure-activity relationships are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.006
• 作为产物：
  描述：

  1-(4-(benzyloxy)phenyl)prop-2-en-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、300.01 kPa 条件下， 反应 40.0h， 生成 4-(tetrahydrofuran-2-yl)phenol
  参考文献：
  名称：

  Novel and highly potent histamine H3 receptor ligands. Part 1: withdrawing of hERG activity

  摘要：

  Pre-clinical investigation of some aryl-piperidinyl ether histamine H3 receptor antagonists revealed a strong hERG binding. To overcome this issue, we have developed a QSAR model specially dedicated to H3 receptor ligands. This model was designed to be directly applicable in medicinal chemistry with no need of molecular modeling. The resulting recursive partitioning trees are robust (80-85% accuracy), but also simple and comprehensible. A novel promising lead emerged from our work and the structure-activity relationships are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.006

文献信息

• <i>sp</i>³ C–H Arylation and Alkylation Enabled by the Synergy of Triplet Excited Ketones and Nickel Catalysts
  作者：Yangyang Shen、Yiting Gu、Ruben Martin

  DOI：10.1021/jacs.8b07405

  日期：2018.9.26

  polypyridyl complexes. Additionally, such a platform provides a new strategy for streamlining the synthesis of complex molecules with high levels of predictable site-selectivity and preparative utility. Mechanistic experiments suggest that sp3 C-H abstraction occurs via HAT from the ketone triplet excited state. We believe this study will contribute to a more systematic utilization of triplet excited ketones

  三重酮敏化剂在光化学转化领域中具有核心重要性。尽管二芳基酮的三重激发态的自由基型特征表明触发氢原子转移 (HAT) 和单电子转移 (SET) 过程等的可行性，但它们在通过 sp3 形成 CC 键中用作多面催化剂烷烃原料的 CH 官能化仍然有待探索。在此，我们解锁了一个模块化的光化学平台，利用镍催化剂与简单、廉价且廉价的催化剂之间的协同作用，将丰富的烷烃 sp3 CH 键作为功能手柄锻造 C(sp3)-C(sp2) 和 C(sp3)-C(sp3) 键。模块化二芳基酮。这种方法的特点是范围广，可以从廉价的催化剂和起始前体中获得，从而补充现有的内球 CH 功能化协议或最近的基于铱多吡啶配合物的光氧化还原方案。此外，这样的平台提供了一种新的策略，用于简化复杂分子的合成，具有高水平的可预测位点选择性和制备效用。机理实验表明 sp3 CH 抽象是通过 HAT 从酮三重激发态发生的。我们相信这项研究将有
• Photochemical Arylation of Alkenols: Role of Intermediates and Synthetic Significance
  作者：Stefano Protti、Daniele Dondi、Maurizio Fagnoni、Angelo Albini

  DOI：10.1002/ejoc.200701177

  日期：2008.5

  the intermediacy of a phenonium ion from the addition of the primarily formed triplet phenyl cation to the alkenol double bond. Intramolecular addition of the OH group to form benzyl (aryl) tetrahydrofurans is favored inpolar protic solvents, where hydride shifts to form aryltetrahydropyrans also occur, whereas in ethyl acetate, intermolecular addition of the chloride anion to the phenonium ion takes

  环醚的一锅串联合成是通过将光生苯基阳离子添加到羟基烯烃中获得的。因此，通过 4-氯-N,N-二甲基苯胺、-苯甲醚和-苯酚与β-羟基烯烃和2-苄基四氢呋喃与γ-羟基烯烃的辐照制备2-（或3-）苯基取代的四氢呋喃。使用非末端烯烃 [非对映异构 (E)-和 (Z)-3-己烯-1-醇] 反式-2-乙基-3-芳基四氢呋喃衍生物由两种异构体立体选择性地形成。光反应的输出取决于结构和溶剂，并且通过将主要形成的三线态苯基阳离子添加到烯醇双键的苯鎓离子的中介而合理化。OH基团的分子内加成形成苄基（芳基）四氢呋喃在极性质子溶剂中是有利的，其中氢化物转移形成芳基四氢吡喃也发生，而在乙酸乙酯中，氯阴离子与苯鎓离子发生分子间加成。上述反应的机制也在计算数据的基础上进行了讨论。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• US6812352B2
  申请人：——

  公开号：US6812352B2

  公开（公告）日：2004-11-02
• Novel and highly potent histamine H3 receptor ligands. Part 1: withdrawing of hERG activity
  作者：Nicolas Levoin、Olivier Labeeuw、Thierry Calmels、Olivia Poupardin-Olivier、Isabelle Berrebi-Bertrand、Jeanne-Marie Lecomte、Jean-Charles Schwartz、Marc Capet

  DOI：10.1016/j.bmcl.2011.07.006

  日期：2011.9

  Pre-clinical investigation of some aryl-piperidinyl ether histamine H3 receptor antagonists revealed a strong hERG binding. To overcome this issue, we have developed a QSAR model specially dedicated to H3 receptor ligands. This model was designed to be directly applicable in medicinal chemistry with no need of molecular modeling. The resulting recursive partitioning trees are robust (80-85% accuracy), but also simple and comprehensible. A novel promising lead emerged from our work and the structure-activity relationships are presented. (C) 2011 Elsevier Ltd. All rights reserved.