(4-methylphenethyl)(p-tolyl)sulfane | 1512844-33-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4-methylphenethyl)(p-tolyl)sulfane
• 英文别名: 1-(4-methylphenyl)-2-(4-methylphenylthio)ethane
• CAS: 1512844-33-5
• 化学式: C₁₆H₁₈S
• 分子量: 242.385
• InChiKey: FQKPFPKUCQRPMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (4-methylphenethyl)(p-tolyl)sulfane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-methyl-4-(4-methylphenethylsulfinyl)benzene
  参考文献：
  名称：

  Synthesis of Sulfur-Bridged Polycycles via Pd-Catalyzed Dehydrogenative Cyclization

  摘要：

  A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp(2))-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.

  DOI：

  10.1021/ol502127j
• 作为产物：
  描述：

  Alpha-甲基苯乙烯 、 4-甲苯硫酚 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以89%的产率得到(4-methylphenethyl)(p-tolyl)sulfane
  参考文献：
  名称：

  硫醇对炔烃双氢磺基化锌催化合成二硫缩醛

  摘要：

  锌催化烯烃氢磺基化反应可以在多种溶剂中进行，并通过区域选择性得到相应的产物。炔烃与硫醇的二氢硫基化也可以通过使用锌催化剂来实现，并且该反应优先于单氢硫基化。该反应还可以区域选择性地以优异的产率得到二硫代缩醛。

  DOI：

  10.1055/s-0037-1610302

文献信息

• Acid/Phosphide-Induced Radical Route to Alkyl and Alkenyl Sulfides and Phosphonothioates from Sodium Arylsulfinates in Water
  作者：Ya-mei Lin、Guo-ping Lu、Gui-xiang Wang、Wen-bin Yi

  DOI：10.1021/acs.joc.6b02459

  日期：2017.1.6

  can in situ generate arylsulfenyl radicals. These radicals have high reactivity to react with alkynes, alkenes, and H-phosphine oxides for the synthesis of alkyl and alkenyl sulfides and phosphonothioates. The control experiments and quantum calculations are also performed to gain insights into the generation mechanism of arylsulfenyl radicals. Notably, the chemistry is free of thiol odors, organic solvents

  引入了一种新开发的含有酸和磷的水性体系，在该体系中，无味且稳定的芳基亚磺酸钠可以原位生成芳基亚硫基。这些自由基具有与炔烃，烯烃和H-膦氧化物反应的高反应性，以合成烷基硫化物和烯基硫化物以及硫代磷酸硫代酸酯。还进行了控制实验和量子计算，以深入了解芳基亚硫基自由基的生成机理。值得注意的是，该化学物质不含硫醇气味，有机溶剂和金属。
• Sulfamic acid: An efficient and recyclable catalyst for the regioselective hydrothiolation of terminal alkenes and alkynes with thiols
  作者：Clarissa Helena Rosa、Maura Luise B. Peixoto、Gilber Ricardo Rosa、Benhur Godoi、Fábio Zazyki Galetto、Marcelo Gonçalves Montes D'Oca、Marcelo Godoi

  DOI：10.1016/j.tetlet.2017.08.051

  日期：2017.9

  Herein, we described a new method for the preparation of thioethers through hydrothiolation of alkenes and alkynes, using sulfamic acid as a reusable catalyst. Generally, this new methodology afforded the desired products in very good yields, under metal and solvent-free conditions. Furthermore, the catalyst was easily recovered and reused for further catalytic reactions without loss of activity.

  在这里，我们描述了一种新的方法，该方法通过使用氨基磺酸作为可重复使用的催化剂，通过烯烃和炔烃的氢硫醇化来制备硫醚。通常，这种新方法可以在无金属和无溶剂的条件下以非常高的收率提供所需的产品。此外，该催化剂易于回收并重新用于进一步的催化反应而不会损失活性。
• Brønsted Acid-Assisted Zinc-Catalyzed Markovnikov-Type Hydrothiolation of Alkenes Using Thiols
  作者：Nobukazu Taniguchi

  DOI：10.1021/acs.joc.0c00487

  日期：2020.5.15

  hydrothiolation of alkenes with thiols was achieved in the presence of 4-toluenesulfonic acid. Through this procedure, Markovnikov-type sulfides were synthesized in excellent yields, and the formation of anti-Markovnikov-type sulfides was suppressed. Furthermore, the combination of numerous aryl alkenes with arenethiols or alkyl thiols was achieved using the procedure.

  在4-甲苯磺酸的存在下实现了锌与硫醇的烯烃的区域选择性氢硫醇化反应。通过该程序，以极高的收率合成了马尔可夫尼科夫型硫化物，并且抑制了反马尔可夫尼科夫型硫化物的形成。此外，使用该方法实现了许多芳基烯烃与芳硫醇或烷基硫醇的结合。
• Palladium(II)-Catalyzed <i>ortho</i>-Olefination of Arenes Applying Sulfoxides as Remote Directing Groups
  作者：Binjie Wang、Chuang Shen、Jinzhong Yao、Hong Yin、Yuhong Zhang

  DOI：10.1021/ol402921w

  日期：2014.1.3

  A novel palladium-catalyzed ortho-C(sp(2))-H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the ortho olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities.