2-methylselenobenzofuran | 144499-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-methylselenobenzofuran
• 英文别名: 2-methylselanyl-1-benzofuran
• CAS: 144499-29-6
• 化学式: C₉H₈OSe
• 分子量: 211.122
• InChiKey: GFTAHFUGSOZVRT-UHFFFAOYSA-N

物化性质

• 沸点：
  265.6±22.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-hydroxyacetophenone semicarbazone 在 selenium(IV) oxide 、 potassium carbonate 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 反应 4.0h， 生成 2-methylselenobenzofuran
  参考文献：
  名称：

  炔硫醇盐的亲核分子内环化反应

  摘要：

  2-（邻羟基苯基）-alkynethiolates和-selenolates，通过碱催化的环切割得到的4-（邻-羟基苯基）-1,2,3-噻二唑和1,2,3- selenadiazoles，顺利转化为2-苯并呋喃硫醇盐和-硒醇盐。这些反应性中间体可以高产率烷基化。该反应序列可以用于合成富电子的硫杂冠醚。2-（邻-氨基苯基）-炔硫醇类似地形成2-甲基磺酰亚胺基。

  DOI：

  10.1016/s0040-4020(00)00315-x

文献信息

• An empirical aromaticity index (AIRT) based on “reversion to type” in the hydrolysis of methyl ethers, methyl thioethers, and methyl selenoethers derived from some heterocyclic and homocyclic polyenes
  作者：Brian Capon、Sing Quan Lew

  DOI：10.1016/s0040-4020(01)80460-9

  日期：1992.1

  2-methylthio- and 3-methylthio-benzothiophene, and 2-methylthio-N-methyl-indole. The values of log kex/khyd for these compounds and those of a previous investigation (ref. 4) have been used to define an aromaticity scale based on “reversion to type” (cf ref. 7).

  已研究了以下化合物在CD 3 CN-D 2 O（9：1 v / v）中氢离子催化的水解和氘交换：1-甲氧基，3-甲氧基和1-甲硫基环庚1-， 3，5-三烯，1-甲氧基-环辛酸酯，2-甲硫基，3-甲硫基和2-甲基硒代苯并呋喃，2-甲硫基和3-甲硫基-苯并噻吩和2-甲硫基-N-甲基-吲哚。这些化合物的log k ex / k hyd值和先前研究的值（参考文献4）已用于基于“类型回归”来定义芳香度标度（参见参考文献7）。
• 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。
• Electrochemical Mn-Promoted Radical Selenylation of Boronic Acids with Diselenide Reagents
  作者：Ziyue Chen、Yuan Wang、Chenjian Hu、Daoxin Wang、Peilin Lei、Hong Yi、Yong Yuan、Aiwen Lei

  DOI：10.1021/acs.orglett.2c00607

  日期：2022.5.13

  A powerful and environmentally friendly electrochemical manganese-promoted free radical selenylation reaction between boronic acids and diselenide reagents was established. This electrochemical protocol provides a practically applicable way to a series of valuable organoselenium compounds with the use of easy available materials. Mechanistic experiments implied that the seleno-radical formed via direct

  建立了硼酸和二硒化物试剂之间强大且环保的电化学锰促进的自由基硒化反应。该电化学协议使用易于获得的材料为一系列有价值的有机硒化合物提供了一种实际适用的方法。机械实验表明，通过二硒化物的直接或间接电化学氧化形成的硒自由基可能是该转化中的关键物种。
• ——
  作者：M. L. Petrov、M. A. Abramov、I. P. Abramova、W. Dehaen、Yu. I. Lyakhovetskii

  DOI：10.1023/a:1013832925639

  日期：——

  The reaction of selenium dioxide with o-hydroxyacetophenone semicarbazones gives 4-(2-hydroxyaryl)-1,2,3-selenadiazoles which undergo ready decomposition by the action of potassium carbonate to form benzofuran-2-selenolates. The latter can be alkylated with methyl iodide and benzyl chloride and arylated with 2,4-dinitrochlorobenzene. Intermediate formation of 2-(o-hydroxyphenyl)ethyneselenolate during decomposition of 1,2,3-selenadiazoles was proved by the isolation of methyl o-methoxyphenylethynyl selenide when the substrate was treated with potassium carbonate in the presence of methyl iodide.
• 4-(ortho-hydroxyphenyl)-1,2,3-selenadiazole as a source of 2-benzofuranselenolate
  作者：Michael L. Petrov、Michael A. Abramov、Wim Dehaen、Suzanne Toppet

  DOI：10.1016/s0040-4039(99)00565-1

  日期：1999.5

  The novel 4-(ortho-hydroxyphenyl)-1,2,3-selenadiazole smoothly transforms into 2-benzofuranselenolate through potassium carbonate catalyzed selenadiazole ring cleavage. The presence of alkyneselenolate is proved by the formation of methyl(ortho-methoxy-phenylethynyl)selenide in the presence of methyl iodide. Alkylation and oxidation reactions of 2-benzofuranselenolate are described. (C) 1999 Elsevier Science Ltd. All rights reserved.