2-(萘-2-基氧基)-1-苯基乙酮 | 14538-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(萘-2-基氧基)-1-苯基乙酮
• 英文名称: 2-(naphthalen-2-yloxy)-1-phenylethanone
• 英文别名: 2-(naphthalene-2-yloxy)-1-phenylethanone；2-naphthalen-2-yloxy-1-phenylethanone
• CAS: 14538-46-6
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: ASSYOZGBQVKGEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(萘-2-基氧基)-1-苯基乙酮 在 哌啶 、 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 、 叔丁醇 为溶剂， 反应 4.5h， 生成 5,6-dihydro-4-hydroxy-6-((naphthalen-2-yloxy)methyl)-6-phenyl-3-(phenylthio)pyran-2-one
  参考文献：
  名称：

  Modification and biological evaluation of novel 4-hydroxy-pyrone derivatives as non-peptidic HIV-1 protease inhibitors

  摘要：

  In this study, we have modified 4-hydroxy-pyran-2-ones, especially introduced heteroatoms (S or O) into the substituents, and detected their interactions with the binding pockets of HIV-1 protease (PR). The results indicated that the ethoxyl groups at C-2' and C-5' of the phenyl ring could enhance the affinities to the S (1) ' and S (2) ' pockets and improve the inhibitory activities. The most potent compound 10f with an IC50 of 3.5 nM in enzymatic assay also exhibited good antiviral activity at the cellular level; it exhibited an EC50 value of 2.9 mu M in Simian immunodeficiency virus-infected CEM cells and suppressed the PR activity in 293T cells using western blot analysis.

  DOI：

  10.1007/s00044-010-9307-4
• 作为产物：
  描述：

  2-溴苯乙酮 、 2-萘酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.33h， 生成 2-(萘-2-基氧基)-1-苯基乙酮
  参考文献：
  名称：

  使用科学的微波设备快速优化单模功能中的反应条件，然后进行多模功能中的底物筛选

  摘要：

  近来，已经出现了一种新的设备，其旨在将单模和多模微波设备的优点集中在一个单元中。我们已经评估了该设备在单模函数中快速优化反应条件，然后在多模函数中进行底物筛选的适用性。我们还探讨了在多模微波设备中同时筛选多种底物时反应混合物的微波吸收率差异对产物转化率的影响。我们发现，当反应混合物的微波吸收率由溶剂决定时，在筛选过程中改变底物的加热曲线几乎没有影响。但是，当使用涉及非微波吸收剂溶剂的反应时，情况并非如此。

  DOI：

  10.1016/j.tet.2007.04.074

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2004011410A1

  公开（公告）日：2004-02-05

  Compounds of formula (I):wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  式(I)的化合物：其中变量基团如定义内；用于抑制11βHSD1。
• Versatile Iridicycle Catalysts for Highly Efficient and Chemoselective Transfer Hydrogenation of Carbonyl Compounds in Water
  作者：Dinesh Talwar、Xiaofeng Wu、Ourida Saidi、Noemí Poyatos Salguero、Jianliang Xiao

  DOI：10.1002/chem.201403701

  日期：2014.9.26

  Cyclometalated iridium complexes are shown to be highly efficient and chemoselective catalysts for the transfer hydrogenation of a wide range of carbonyl groups with formic acid in water. Examples include α‐substituted ketones (α‐ether, α‐halo, α‐hydroxy, α‐amino, α‐nitrile or α‐ester), α‐keto esters, β‐keto esters and α,β‐unsaturated aldehydes. The reduction was carried out at substrate/catalyst ratios of

  环金属化铱配合物被证明是高效的化学选择催化剂，可用于在水中用甲酸转移多种羰基的加氢反应。实例包括α-取代的酮（α-醚，α-卤代，α-羟基，α-氨基，α-腈或α-酯），α-酮酸酯，β-酮酸酯和α，β-不饱和醛。在pH 4.5下，还原反应的底物/催化剂比例最高为50000，并且不需要有机溶剂。该方案为合成β-官能化的仲醇（例如β-羟基醚，β-羟胺和β-羟基卤化物）提供了一种实用，简便且有效的方法，它们是医药，精细化工，香料和农业化学合成中的重要中间体。
• Exogenous-oxidant-free electrochemical oxidative C–H sulfonylation of arenes/heteroarenes with hydrogen evolution
  作者：Yong Yuan、Yi Yu、Jin Qiao、Pan Liu、Banying Yu、Wukun Zhang、Huilin Liu、Min He、Zhiliang Huang、Aiwen Lei

  DOI：10.1039/c8cc06451b

  日期：——

  An efficient and environmentally benign electrochemical oxidative radical C–H sulfonylation of arenes/heteroarenes was developed in this work. A series of significant diarylsulfones were prepared under mild catalyst- and exogenous-oxidant-free reaction conditions, which efficiently avoid the issues of desulfonylation or over-reduction of sulfonyl groups.

  在这项工作中，开发了一种有效且环境友好的芳烃/杂芳烃电化学氧化自由基C–H磺酰化方法。在温和的无催化剂和无外源氧化剂的反应条件下制备了一系列重要的二芳基砜，这有效地避免了磺酰基的磺酰化或过度还原的问题。
• Solid-State Synthesis, Characterization, Biological Studies and Theoretical Evaluation of (E)-2-(2-(naphthalene-2-yloxy)-1-phenylethylidene) Hydrazine Thiocarboxamide
  作者：G. Rajmohan、G. Ravindran、G. Arivazhagan

  DOI：10.13005/ojc/370312

  日期：2021.6.30

  The title compound (E)-2-(2-(naphthalene-2-yloxy)-1-phenylethylidene) hydrazine thiocarboxamide (NAPTCAR) is synthesized by condensing 2-(Naphthalen-2-yloxy)-1-phenyl-ethanone (2-NAPETH) with thiosemicarbazide in 1: 1 molar ratio in solid state medium. Purity of compounds has been confirmed by Thin Layer Chromatography. Characterization and structure elucidation of these ligands have been made using 1H NMR, 13C NMR and FTIR spectral studies and DFT calculations. Interestingly, 13C NMR spectrum of thiosemicarbazone ligand exhibits the presence of two conformational structures. The HOMO – LUMO energy gap of conformer A is found to be almost equal to that of conformer B. Conformer A is has relatively a stronger nucleophilic character than conformer B as indicated by the molecular electrostatic potential surface. Van der Waals and the steric interactions play a dominant role in stabilizing the structure of both the conformers. The ligands have been examined for antibacterial and antifungal activities and are quite active in this respect.

  标题化合物(E)-2-(2-(萘基氧基)-1-苯基乙烯基)硫代甲酰肼（NAPTCAR）是通过在固态介质中以1:1的摩尔比将2-(萘基氧基)-1-苯基乙酮（2-NAPETH）与硫代氨基甲酰肼缩合合成的。化合物的纯度已通过薄层色谱确认。这些配体的表征和结构阐明是通过1H NMR、13C NMR和FTIR光谱研究以及DFT计算完成的。有趣的是，硫代氨基甲酰肼配体的13C NMR谱显示了两种构象结构的存在。构象A的HOMO - LUMO能隙几乎等于构象B的能隙。构象A的亲核性较构象B更强，这由分子静电势表面所指示。范德华和立体作用在稳定两种构象的结构中起主导作用。这些配体已经进行了抗菌和抗真菌活性的检测，在这方面表现出相当活跃。
• Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent
  作者：Zhanwei Ma、Min Zhou、Lin Ma、Min Zhang

  DOI：10.1177/1747519820907244

  日期：2020.7

  acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare

  由伊顿试剂（五氧化二磷-甲磺酸）促进的 α-苯氧基酮的环脱水用于在温和条件下以中等至优异的产率制备 3-取代或 2,3-二取代的苯并呋喃。该方法提供了从容易获得的起始材料（如苯酚和 α-溴酮）中轻松获得苯并呋喃的途径。反应效率高，这归功于伊顿试剂良好的反应性和流动性。该反应可用于制备萘并呋喃香豆素、苯并噻吩和苯并吡喃。