(2-methylbutyl)(p-tolyl)sulfane | 1286763-64-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2-methylbutyl)(p-tolyl)sulfane
• 英文别名: 2-methylbutyl 4-methylphenylsulfide；2-methylbutyl 4-tolyl sulfide；(2-methylbutyl)(4-methylphenyl)sulfane；1-Methyl-4-(2-methylbutylsulfanyl)benzene
• CAS: 1286763-64-1
• 化学式: C₁₂H₁₈S
• 分子量: 194.341
• InChiKey: ZHWQGASGOYTZRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基-1-丁硫醇 在 N-氯代丁二酰亚胺 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 (2-methylbutyl)(p-tolyl)sulfane
  参考文献：
  名称：

  N-氯代丁二酰亚胺与格氏试剂在硫醇的交叉偶联反应下合成芳基硫醚

  摘要：

  描述了一种在N-氯代琥珀酰亚胺存在下通过硫醇与格氏试剂的偶联来合成芳基硫化物的方便的一锅法。当用N-氯代琥珀酰亚胺处理硫醇时，形成了亚硫酰氯，然后在温和的反应条件下，将所得的亚硫酰氯与格氏试剂直接反应，以良好的收率获得了芳基硫化物。所用的反应条件容许包括酯，氟和氯的官能团。重要的是要注意，该方法的反应时间短（总计30分钟），是现有方案中芳基硫醚合成的另一种方法。

  DOI：

  10.1021/jo302088t

文献信息

• Microwave-Assisted Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides in Water
  作者：Chin-Fa Lee、Yi-An Chen、Satpal Badsara、Wan-Ting Tsai

  DOI：10.1055/s-0034-1379206

  日期：——

  C–S bond formation from thiols and aryl iodides in the presence of a copper catalyst is reported. A combination of copper(II) oxide and 1,10-phenanthroline catalyzes this reaction. A variety of aryl iodides react smoothly with thiols to provide the corresponding aryl sulfides in good to excellent yields. Notably, the reactions proceed in water with a short reaction time (30 minutes). This system shows

  摘要 据报道，在铜催化剂存在下，由硫醇和碘代甲烷形成的微波促进了C–S键的形成。氧化铜（II）和1,10-菲咯啉的组合催化该反应。各种芳基碘化物可与硫醇平稳反应，以良好至极佳的收率提供相应的芳基硫化物。值得注意的是，反应在水中以短的反应时间（30分钟）进行。该系统显示了广泛的功能组耐受性；氨基，氯，溴，乙酰基和硝基不受反应条件的影响。 据报道，在铜催化剂存在下，由硫醇和碘代甲烷形成的微波促进了C–S键的形成。氧化铜（II）和1,10-菲咯啉的组合催化该反应。各种芳基碘化物可与硫醇平稳反应，以良好至极佳的收率提供相应的芳基硫化物。值得注意的是，反应在水中以短的反应时间（30分钟）进行。该系统显示了广泛的功能组耐受性；氨基，氯，溴，乙酰基和硝基不受反应条件的影响。
• An Efficient Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides
  作者：Hsin-Lun Kao、Chin-Keng Chen、Yu-Jen Wang、Chin-Fa Lee

  DOI：10.1002/ejoc.201001667

  日期：2011.3

  Cu 2 O powder is a very reactive catalyst for the coupling of thiols to aryl iodides. A variety of functional groups including esters, unprotected amines, alcohols, and heterocycles tolerate the reaction conditions. Moreover, di-ortho-substituted aryl iodides with sterically demanding substrates were also coupled to give the desired aryl thioethers in good to excellent yields.

  市售的 Cu 2 O 粉末是一种非常活泼的催化剂，用于将硫醇偶联到芳基碘化物上。包括酯、未保护胺、醇和杂环在内的多种官能团可耐受反应条件。此外，二邻位取代的芳基碘化物与空间要求严格的底物也被偶联，以良好至极好的产率得到所需的芳基硫醚。
• Copper Mediated Formation of Carbon-Heteroatom Bonds Using Organoboron Reagents and Ultrasound
  作者：George W. Kabalka、Bryan J. Musolino

  DOI：10.3987/com-14-s(k)18

  日期：——

  This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%(1) Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.
• A general rhodium-catalyzed cross-coupling reaction of thiols with aryl iodides
  作者：Chih-Shin Lai、Hsin-Lun Kao、Yan-Jhang Wang、Chin-Fa Lee

  DOI：10.1016/j.tetlet.2012.06.054

  日期：2012.8

  The general procedure for the rhodium-catalyzed cross-coupling of thiols with aryl iodides is described. The catalytic system consists of 5 mol % of [RhCl(cod)](2) and 10 mol % of PPh3 as a ligand. A variety of aryl iodides reacted with thiols, giving aryl thioethers in good to excellent yields. It is important to note that the deactivated aryl iodides such as 4-iodoanisole is worked smoothly to provide the corresponding aryl thioethers in excellent yields. Functional groups such as free-amines, chloro, are all tolerated under the employed reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.
• US7252785B2
  申请人：——

  公开号：US7252785B2

  公开（公告）日：2007-08-07