2-butyl-4-hex-1-ynylthiophene | 1403460-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-butyl-4-hex-1-ynylthiophene
• 英文别名: 2-butyl-4-(hex-1-yn-1-yl)thiophene；2-Butyl-4-hex-1-ynylthiophene
• CAS: 1403460-01-4
• 化学式: C₁₄H₂₀S
• 分子量: 220.379
• InChiKey: GGIKURGYAINASX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  7-(mercaptomethyl)trideca-5,8-diyn-7-ol 在 potassium iodide 、 palladium(II) iodide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以52%的产率得到2-butyl-4-hex-1-ynylthiophene
  参考文献：
  名称：

  Synthesis of Substituted Thiophenes by Palladium-Catalyzed Heterocyclodehydration of 1-Mercapto-3-yn-2-ols in Conventional and Nonconventional Solvents

  摘要：

  A variety of readily available 1-mercapto-3-yn-2-ols 5 were conveniently converted into the corresponding thiophenes 6 in good to high yields in MeOH as the solvent at 50-100 degrees C in the presence of catalytic amounts (1-2%) of PdI2 in conjunction with KI (KI:PdI2 molar ratio = 10). The catalyst could be made recyclable employing an ionic liquid, such as BmimBF(4), as the solvent under suitable conditions.

  DOI：

  10.1021/jo301943k

文献信息

• Palladium catalysis with sulfurated substrates under aerobic conditions: A direct oxidative carbonylation approach to thiophene-3-carboxylic esters
  作者：Raffaella Mancuso、Romina Strangis、Ida Ziccarelli、Nicola Della Ca'、Bartolo Gabriele

  DOI：10.1016/j.jcat.2020.11.032

  日期：2021.1

  The first example of a palladium-catalyzed oxidative carbonylative S-cyclization process carried out under aerobic conditions is reported. The method is based on the use of the PdI2/KI catalytic system and an acetylenic substrate bearing a sulfurated group in suitable position for attacking the coordinated triple bond. To avoid the possible oxidation of a free thiol group, a methylthio group was used

  据报道在有氧条件下进行的钯催化的氧化羰基S-环化反应的第一个例子。该方法基于使用PdI 2 / KI催化体系和在合适位置带有带有硫酸化基团的炔属底物以攻击配位三键的方法。为了避免游离硫醇基的可能的氧化，使用甲硫基作为硫亲核试剂，因为硫的甲基可以在反应条件下通过与碘化物阴离子反应除去而得到甲基碘。特别是，我们已经采用作为底物1-（甲硫基）-3-炔-2-醇，其在小号-环化，去甲基化和烷氧基羰基化反应，一步一步生成噻吩-3-羧酸酯，在醇中作为外部亲核试剂和溶剂，在40 atm的CO-空气4：1混合物（空气是氧气的来源，用作外部氧化剂）。源自烷氧基羰基化过程的Pd（0）物种在氧与烷氧基羰基化步骤以及水侵蚀到碘甲烷的结合作用下，通过氧的作用与氧共同作用，被氧化为具有催化活性的PdI 2。这种新的合成转化可以成功地应用于各种不同取代的1-（甲硫基）-3-yn-2-ol，包括带有双二烷基取代基的底物。
• Synthesis of Substituted Thiophenes by Palladium-Catalyzed Heterocyclodehydration of 1-Mercapto-3-yn-2-ols in Conventional and Nonconventional Solvents
  作者：Bartolo Gabriele、Raffaella Mancuso、Lucia Veltri、Vito Maltese、Giuseppe Salerno

  DOI：10.1021/jo301943k

  日期：2012.11.2

  A variety of readily available 1-mercapto-3-yn-2-ols 5 were conveniently converted into the corresponding thiophenes 6 in good to high yields in MeOH as the solvent at 50-100 degrees C in the presence of catalytic amounts (1-2%) of PdI2 in conjunction with KI (KI:PdI2 molar ratio = 10). The catalyst could be made recyclable employing an ionic liquid, such as BmimBF(4), as the solvent under suitable conditions.