3-methoxybenzyl p-tolyl sulfane | 947527-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxybenzyl p-tolyl sulfane
• 英文别名: 1-Methoxy-3-[(4-methylphenyl)sulfanylmethyl]benzene
• CAS: 947527-83-5
• 化学式: C₁₅H₁₆OS
• 分子量: 244.357
• InChiKey: SZKODGLWIAJMJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxybenzyl p-tolyl sulfane 在 palladium diacetate 、 Selectfluor 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 25.0h， 生成 (E)-ethyl 3-(4-methoxy-2-(p-tolylsulfinylmethyl)phenyl)acrylate
  参考文献：
  名称：

  Palladium(II)-Catalyzed ortho-Olefination of Arenes Applying Sulfoxides as Remote Directing Groups

  摘要：

  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.

  DOI：

  10.1021/ol402921w
• 作为产物：
  描述：

  4-甲苯硫酚 、 3-甲氧基溴苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-methoxybenzyl p-tolyl sulfane
  参考文献：
  名称：

  硫醚作为钯催化的芳烃直接芳基化的导向基团

  摘要：

  硫醚已被证明是在钯催化下芳烃芳基化的有效导向基团。硫醚基可以容易地除去或转化为其他官能团。动力学同位素效应研究表明，芳烃的CH裂解可能是限制营业额的步骤。

  DOI：

  10.1002/adsc.201200447

文献信息

• Ir(<scp>iii</scp>)-catalyzed thioether directed arene C–H alkenylation
  作者：Chen Li、Xian Chen、Rui-Peng Bao、Dong-Li Li、Kun Zhang、Dong-Hui Wang

  DOI：10.1039/c9ra06811b

  日期：——

  In this study, we demonstrate an Ir(III)-catalyzed thioether directed alkenylation of arene C–H bonds under mild reaction conditions. The selectivity for mono- or di-alkenylation is controlled by the concentration of alkene and oxidant loading. Various functional groups are tolerated, and moderate to good yields of alkenylated products are achieved.

  在这项研究中，我们展示了在温和反应条件下Ir( III ) 催化的硫醚定向烯基化芳烃 C-H 键。单或二烯基化的选择性由烯烃浓度和氧化剂负载量控制。可耐受各种官能团，并获得中等至良好的烯基化产物产率。
• Palladium-Catalyzed C-H Acylation of Arenes Using Thioethers as Directing Groups
  作者：Bo Xu、Wei Liu、Chunxiang Kuang

  DOI：10.1002/ejoc.201400096

  日期：2014.4

  Thioethers have been proven to be reliable directing groups for palladium catalyzed alkenylation of arenes via C–H activation. Mechanistic investigation reveals that the C–H cleavage of arenes is the turnover-limiting step, and an acetate-bridged dinuclear cyclopalladation intermediate is involved. The alkenylated thioethers can be easily removed and transformed into a variety of useful groups.

  硫醚已被证明是钯催化芳烃通过 C-H 活化进行烯基化的可靠导向基团。机理研究表明，芳烃的 C-H 裂解是转换限制步骤，并且涉及乙酸桥联的双核环钯化中间体。烯基化硫醚可以很容易地去除并转化为各种有用的基团。
• Unusual Deoxidative Coupling Reaction of β-Sulfinyl Esters with Benzylic Trimethylammonium Salts
  作者：Qiaoling Zhang、Hang Feng、Feng Chen、Ze He、Qingle Zeng

  DOI：10.1021/acs.joc.1c00615

  日期：2021.6.4

  A KOH-promoted unusual deoxidative coupling reaction of β-sulfinyl esters with benzylic trimethylammonium salts to produce thioethers is discovered for the first time. If quaternary ammonium salts synthesized from enantiomerically enriched amines are adopted, highly enantiomerically enriched benzyl thioethers (>95–99% ee) with configurations opposite to those of the enantiomerically enriched amines

  首次发现了 KOH 促进的 β-亚磺酰基酯与苄基三甲基铵盐的不寻常脱氧偶联反应生成硫醚。如果采用由对映体富集的胺合成的季铵盐，则获得与对映体富集的胺具有相反构型的高度对映体富集的苄基硫醚（> 95-99％ee）。
• Synthesis of Sulfur-Bridged Polycycles via Pd-Catalyzed Dehydrogenative Cyclization
  作者：Binjie Wang、Yue Liu、Cong Lin、Yiming Xu、Zhanxiang Liu、Yuhong Zhang

  DOI：10.1021/ol502127j

  日期：2014.9.5

  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.