2-((4-methoxyphenyl)selanyl)pyridine | 1350663-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-((4-methoxyphenyl)selanyl)pyridine
• 英文别名: 2-(4-Methoxyphenyl)selanylpyridine
• CAS: 1350663-38-5
• 化学式: C₁₂H₁₁NOSe
• 分子量: 264.185
• InChiKey: VVMSNALIWGLBNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯吡啶 、 bis(4-methoxyphenyl)diselenide 在 次磷酸 、 甘油 作用下， 以 水 为溶剂， 反应 2.5h， 以97%的产率得到2-((4-methoxyphenyl)selanyl)pyridine
  参考文献：
  名称：

  Glycerol/hypophosphorous acid: an efficient system solvent-reducing agent for the synthesis of 2-organylselanyl pyridines

  摘要：

  We describe herein an efficient and simple method to synthesize 2-organylselanyi pyridines by reactions of 2-chloropyridines with organylselenols, generated in situ by reaction of diorganyl diselenides, using glycerol as solvent and hypophosphorous acid (H3PO2) as reducing agent. Using this methodology, a range of selenium substituted pyridines was obtained in high yields. The system solvent-reducing agent glycerol/H3PO2 can be easily recovered and reused for five times without loss of efficiency. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.057

文献信息

• An electrochemical method for deborylative selenylation of arylboronic acids under metal- and oxidant-free conditions
  作者：Zhengjiang Fu、Jian Yin、Dongdong He、Xuezheng Yi、Shengmei Guo、Hu Cai

  DOI：10.1039/d1gc02962b

  日期：——

  An efficient protocol to synthesize aryl selenoethers through deborylative selenylation of widely available arylboronic acids has been established under electrochemical conditions in the absence of metal catalyst and external oxidant. The synthesis of bioactive molecules and gram-scale transformation have been performed to highlight the synthetic utility of the protocol. CV (cyclic voltammetry) experiment

  在没有金属催化剂和外部氧化剂的电化学条件下，建立了一种通过广泛使用的芳基硼酸的脱硼硒基化合成芳基硒醚的有效方案。已经进行了生物活性分子的合成和克级转化，以突出该协议的合成效用。CV（循环伏安法）实验表明，在标准条件下，二硒化物的阳极氧化发生在芳基硼酸底物的阳极氧化之前。
• Silver-Catalyzed Synthesis of Diaryl Selenides by Reaction of Diaryl Diselenides with Aryl Boronic Acids
  作者：Bruna Goldani、Vanessa G. Ricordi、Natália Seus、Eder J. Lenardão、Ricardo F. Schumacher、Diego Alves

  DOI：10.1021/acs.joc.6b02108

  日期：2016.11.18

  We described herein our results on the silver-catalyzed synthesis of diaryl selenides via a cross-coupling reaction of diaryl diselenides with aryl boronic acids. The methodology is tolerant to electron-donor and electron-withdrawing groups at the substrates and the desired products were obtained in good to excellent yields.

  我们在本文中描述了通过二芳基二硒化物与芳基硼酸的交叉偶联反应在银催化的二芳基硒化物的合成中的结果。该方法耐受底物上的电子给体和吸电子基团，并且以良好至优异的产率获得了所需的产物。
• Synthesis of diaryl selenides using electrophilic selenium species and nucleophilic boron reagents in ionic liquids
  作者：Camilo S. Freitas、Angelita M. Barcellos、Vanessa G. Ricordi、Jesus M. Pena、Gelson Perin、Raquel G. Jacob、Eder J. Lenardão、Diego Alves

  DOI：10.1039/c1gc15725f

  日期：——

  We described herein the use of imidazolium ionic liquids [bmim]PF6 and [bmim]BF4 in the selective, metal and catalyst-free synthesis of unsymmetrical diaryl selenides by electrophilic substitution in arylboron reagents with arylselenium halides (Cl and Br) at room temperature. This is a general substitution reaction and it was performed with arylboronic acids or potassium aryltrifluoroborates bearing

  我们在此描述了咪唑鎓的用途 离子液体[bmim] PF 6和[bmim] BF 4在选择性，金属和催化剂室温下，通过芳基硼试剂中的芳基硒化卤化物（Cl和Br）进行亲电取代，可无规合成不对称的二芳基硒化物。这是一般的取代反应，是用带有吸电子或给电子基团的芳基硼酸或芳基三氟硼酸钾进行的，从而以良好或优异的收率提供了相应的二芳基硒化物。这离子液体[bmim] [PF 6 ]易于回收，可用于进一步的取代反应。
• Nickel-Сatalyzed Carbon–Selenium Bond Formations under Mild Conditions
  作者：Serik Zhumagazy、Chen Zhu、Huifeng Yue、Magnus Rueping

  DOI：10.1055/s-0042-1752655

  日期：——

  offers facile access to various unsymmetrical selenium-containing motifs. The reaction features excellent functional group tolerance, wide substrate scope, good efficiency, and operates under mild reaction conditions. Notably, this protocol could be readily scaled up to gram scale without the loss of yield.

  描述了芳基碘化物和硒醇之间的镍催化 C-Se 交叉偶联。新开发的催化方法可以轻松访问各种不对称的含硒基序。该反应具有优异的官能团耐受性、底物适用范围广、效率高、反应条件温和等特点。值得注意的是，该协议可以很容易地扩大到克级，而不会损失产量。
• Bhasin, K. K.; Gujral, Gurjeet; Gulati, Shivani, Indian Journal of Heterocyclic Chemistry, 2021, vol. 31, # 3, p. 497 - 503
  作者：Bhasin, K. K.、Gujral, Gurjeet、Gulati, Shivani

  DOI：——

  日期：——