2-(phenylselanyl)naphthalen-1-ol | 78617-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(phenylselanyl)naphthalen-1-ol
• 英文别名: 2-Phenylselenenyl-naphthol；2-phenylselanylnaphthalen-1-ol
• CAS: 78617-32-0
• 化学式: C₁₆H₁₂OSe
• 分子量: 299.231
• InChiKey: QBIQYUJGANHVLV-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  441.4±28.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-methoxy-2-phenylselanyl-naphthalene 在 甲基碘化镁 、 xylene 作用下， 生成 2-(phenylselanyl)naphthalen-1-ol
  参考文献：
  名称：

  Keimatsu; Yokota; Satoda, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1933, vol. 53, p. 993,1029; dtsch. Ref. S. 203, 206

  摘要：

  DOI：

文献信息

• Ammonium Salt-Catalyzed Highly Practical <i>Ortho</i>-Selective Monohalogenation and Phenylselenation of Phenols: Scope and Applications
  作者：Xiaodong Xiong、Ying-Yeung Yeung

  DOI：10.1021/acscatal.8b00327

  日期：2018.5.4

  An ortho-selective ammonium chloride salt-catalyzed direct C–H monohalogenation of phenols and 1,1′-bi-2-naphthol (BINOL) with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) as the chlorinating agent has been developed. The catalyst loading was low (down to 0.01 mol %) and the reaction conditions were very mild. A wide range of substrates including BINOLs were compatible with this catalytic protocol. Chlorinated

  以1,3-二氯-5,5-二甲基乙内酰脲（DCDMH）作为氯化剂的邻位选择性氯化铵盐催化的苯酚和1,1'-联-2-萘酚（BINOL）的直接C–H单卤化反应具有已开发。催化剂负载量低（低至0.01mol％），反应条件非常温和。包括BINOL在内的多种底物均与该催化方案兼容。氯化的BINOL是有用的合成子，用于合成范围广泛的不容易合成的不对称3-芳基BINOL。另外，相同的催化体系可以促进酚的邻位选择性硒化。
• Metal-Free Synthesis of Phenol-Aryl Selenides via Dehydrogenative C–Se Coupling of Aryl Selenoxides with Phenols
  作者：Zhengfen Liu、Yonggang Jiang、Chunxiang Liu、Linlin Zhang、Jing Wang、Tiantian Li、Hongbin Zhang、Minyan Li、Xiaodong Yang

  DOI：10.1021/acs.joc.0c00792

  日期：2020.6.5

  Herein, we disclose the synthesis of diaryl selenides through an unexpected C–Se coupling between aryl benzyl selenoxides and phenols. The synthetic significance of the method is that it provides a mild, rapid, and metal-free access to organoselenides in high yields with excellent functional group tolerance. This coupling of aryl benzyl selenoxides reveals a completely new reaction possibility compared

  在这里，我们公开了通过芳基苄基亚硒酸酯和苯酚之间意外的C-Se偶联合成二芳基硒化物的方法。该方法的综合意义在于，它可提供温和，快速且无金属的有机硒化物，且具有出色的官能团耐受性。与芳基亚砜相比，芳基苄基亚硒酸酯的这种偶联揭示了全新的反应可能性。我们还通过实验研究探索了这种意外转变的反应机理，并揭示了一种特殊的Se（IV）-Se（III）-Se（II）反应途径。
• Copper-Mediated Regioselective C–H Sulfenylation and Selenation of Phenols with Phenanthroline Bidentate Auxiliary
  作者：Rikuo Kajiwara、Kazutaka Takamatsu、Koji Hirano、Masahiro Miura

  DOI：10.1021/acs.orglett.0c02012

  日期：2020.8.7

  A copper-mediated, phenanthroline-directed highly ortho-selective C–H sulfenylation of phenols with diaryl disulfides proceeds to form the corresponding unsymmetrical diaryl sulfides in good yield. The key to success is the introduction of a phenanthroline directing group of the bidentate-chelating nature, which is easily attachable, detachable, and even recyclable. Moreover, the same strategy is applicable

  铜介导的，邻菲咯啉指导的苯酚与二芳基二硫化物的高邻位选择性C–H亚磺酰基化反应以高收率形成相应的不对称二芳基硫化物。成功的关键是引入具有双齿螯合性质的菲咯啉导向基团，该基团易于连接，分离，甚至可回收。此外，相同的策略适用于C–H硒化，使二芳基硒化物具有高效率和区域选择性。
• Transition-Metal-Free Selective Oxidative C(sp³)–S/Se Coupling of Oxindoles, Tetralone, and Arylacetamides: Synthesis of Unsymmetrical Organochalcogenides
  作者：Ch. Durga Prasad、Moh. Sattar、Sangit Kumar

  DOI：10.1021/acs.orglett.6b03735

  日期：2017.2.17

  selenides from the sp3-C–H bond of oxindole, tetralone, arylacetamide, and aryl chalcogenide precursors. Sulfones were obtained from sodium sulfinates using potassium iodide, tert-butyl hydroperoxide in DMSO, and acetic acid. Sulfides and selenides were prepared from diaryl disulfides or diselenides employing potassium tert-butoxide in DMSO. α-Tetralone underwent concomitant chalcogenation and aromatization

  已经开发了无过渡金属的合成方法，用于制备不对称的二芳基和芳基烷基硫属元素化物：砜，硫化物和硒化物，这些化合物是由吲哚，四氢萘酮，芳基乙酰胺和芳基硫属元素化物前体的sp 3 -C键形成的。使用碘化钾，在DMSO中的叔丁基氢过氧化物和乙酸从亚磺酸钠中获得砜。使用叔丁醇钾在DMSO中由二芳基二硫化物或二硒化物制备硫化物和硒化物。α-四氢萘酮同时进行硫属元素化和芳构化，导致一锅中生成2-硫属元素基-1-萘酚。
• Oxidation of phenols, pyrocatechols, and hydroquinones to ortho-quinones using benzeneseleninic anhydride
  作者：Derek H. R. Barton、Andrew G. Brewster、Steven V. Ley、Christine M. Read、Moshe N. Rosenfeld

  DOI：10.1039/p19810001473

  日期：——

  Benzeneseleninic anhydride has been used as a mild oxidising reagent to convert phenols into o-quinones including some examples where the p-position is unblocked. The method is limited to the production of o-quinones which are not susceptible to further reaction. Pyrocatechols and hydroquinones can also be oxidised to the corresponding quinones in excellent yield using benzeneseleninic anhydride.

  苯硒酸酐已被用作温和的氧化剂，以将苯酚转化为邻醌，包括一些对位未被保护的例子。该方法限于不易发生进一步反应的邻醌的生产。还可以使用苯硒二酸酐将邻苯二酚和对苯二酚氧化成相应的醌，收率很高。