7-methyl-2-phenyl-1,4-naphthoquinone | 211362-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-methyl-2-phenyl-1,4-naphthoquinone
• 英文别名: 7-methyl-2-phenylnaphthalene-1,4-dione
• CAS: 211362-46-8
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: DSBRGXJXDGAQHL-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  450.3±45.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(4-methyl-2-(phenylethynyl)phenyl)ethan-1-one 在 copper(l) iodide 、 copper(II) bis(trifluoromethanesulfonate) 、 二甲基亚砜 作用下， 反应 8.0h， 以70%的产率得到7-methyl-2-phenyl-1,4-naphthoquinone
  参考文献：
  名称：

  CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones: Efficient synthesis of 1,4-naphthoquinones

  摘要：

  A concise and efficient method for the synthesis of 1,4-naphthoquinones has been successfully developed involving a CuI/Cu(OTf)(2)/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl) arylketones. The present protocol provided a novel approach to access functionalized 1,4-naphthoquinones from non-naphthoquinone precursors with good selectivity and functional group tolerance. (C) 2019 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2019.05.066

文献信息

• Synthesis of Novel Quinone Boronic Ester Derivatives via a Highly Regioselective Cr-Mediated Benzannulation Reaction and Their Application in Pd-Catalyzed Coupling Processes
  作者：Mark W. Davies、Christopher N. Johnson、Joseph P. A. Harrity

  DOI：10.1021/jo010098f

  日期：2001.5.1

  have been found to undergo Pd-catalyzed coupling reactions with a range of aryl and allyl halides and provides a strategy for the selective and predictable preparation of highly substituted quinones and hydroquinones. Finally, the propensity of this technique to prepare highly functionalized aromatic compounds in an expeditious fashion is demonstrated in the total synthesis of dimeric carbazole (+/-

  本文描述了一类新型的醌硼酸酯的合成和反应性。这些化合物是利用Fischer卡宾配合物与炔基硼酸酯的高度区域选择性Dötz环化法制备的。迄今研究的所有底物均提供了单一的区域异构芳基硼酸酯产品。在空间和电子效应的背景下讨论了这种选择性的起源。另外，已经发现这些化合物与一系列芳基和烯丙基卤化物进行Pd催化的偶联反应，并提供了选择性和可预测地制备高度取代的醌和对苯二酚的策略。最后，
• The microwave-assisted Dötz benzannulation process
  作者：Edward J. Hutchinson、William J. Kerr、Euan J. Magennis

  DOI：10.1039/b206981b

  日期：——

  Chromium carbene-mediated Dötz benzannulation has been shown to proceed remarkably rapidly and with enhanced efficiency under developed microwave-assisted conditions.

  铬卡宾介导的 Dötz 苯环化已被证明在发达的微波辅助条件下进行得非常快并且效率提高。
• Approaching ambient temperatures in 1,2-DCE to deliver efficient intermolecular Dötz benzannulation processes
  作者：Stephanie Irvine、William J. Kerr、Allan R. McPherson、Colin M. Pearson

  DOI：10.1016/j.tet.2007.09.088

  日期：2008.1

  Conditions have been developed that enable intermolecular Dotz benzannulations to be carried out under extremely mild conditions, using 1,2-DCE as the reaction solvent and without the requirement for any additional reaction promoters. The new protocols, at temperatures close to ambient, have been applied successfully to a range of internal and terminal alkynes with a series of aryl and alkenyl carbene complexes, resulting in good to high yields of the benzannulation products. The developed conditions did, however, return lower benzannulation yields when utilised with the traditionally more troublesome 2-furyl carbene complex. It was found that increased reaction temperatures in 1,2-DCE did deliver high yields for the processes with this heteroaryl species. (c) 2007 Elsevier Ltd. All rights reserved.
• Thaplial, Prakash Chander, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 5, p. 477 - 479
  作者：Thaplial, Prakash Chander

  DOI：——

  日期：——
• CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones: Efficient synthesis of 1,4-naphthoquinones
  作者：Bingwei Zhou、Qian Liu、Heng Wang、Hongwei Jin、Yunkui Liu

  DOI：10.1016/j.tet.2019.05.066

  日期：2019.7

  A concise and efficient method for the synthesis of 1,4-naphthoquinones has been successfully developed involving a CuI/Cu(OTf)(2)/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl) arylketones. The present protocol provided a novel approach to access functionalized 1,4-naphthoquinones from non-naphthoquinone precursors with good selectivity and functional group tolerance. (C) 2019 Published by Elsevier Ltd.