S-phenyl naphthalene-1-carbothioate | 24197-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: S-phenyl naphthalene-1-carbothioate
• 英文别名: S-phenyl 1-naphthalenecarbothioate；[1]thionaphthoic acid S-phenyl ester；[1]Thionaphthoesaeure-S-phenylester；Thionaphthoesaeure-1-S-phenylester
• CAS: 24197-80-6
• 化学式: C₁₇H₁₂OS
• 分子量: 264.348
• InChiKey: HEGWCHVLXZVBMW-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  413.9±18.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-phenyl naphthalene-1-carbothioate 在 bis(1,5-cyclooctadiene)nickel (0) 、 三环己基膦 作用下， 以 甲苯 为溶剂， 以99%的产率得到1-苯基硫烷基萘
  参考文献：
  名称：

  Palladium- and Nickel-Catalyzed Decarbonylative C–S Coupling to Convert Thioesters to Thioethers

  摘要：

  This Letter describes the development of a catalytic decarbonylative C-S coupling reaction that transforms thioesters into thioethers. Both Pd- and Ni-based catalysts are developed and applied to the construction of diaryl, aryl alkyl, and heterocycle-containing thioethers.

  DOI：

  10.1021/acs.orglett.7b03305
• 作为产物：
  描述：

  phenylmagnesium bromide 在 sulfur 作用下， 生成 S-phenyl naphthalene-1-carbothioate
  参考文献：
  名称：

  Szperl; Herszaft, Roczniki Chemii, 1934, vol. 14, p. 1238,1239, 1241

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Thiocarbonylation of Aryl, Vinyl, and Benzyl Bromides
  作者：Mia N. Burhardt、Andreas Ahlburg、Troels Skrydstrup

  DOI：10.1021/jo5009965

  日期：2014.12.19

  A catalytic protocol for synthesis of thioesters from aryl, vinyl, and benzyl bromides as well as benzyl chlorides was developed using only stoichiometric amounts of carbon monoxide, produced from a solid CO precursor inside a two-chamber system. As a catalytic system, the combination of bis(benzonitrile) palladium(II) chloride and Xantphos furnished the highest yields of the desired compounds, along

  使用芳烃，乙烯基和苄基溴化物以及苄基氯来合成硫酯的催化方案仅使用化学计量量的一氧化碳开发，该一氧化碳是由两室系统中的固态CO前驱体产生的。作为催化体系，双（苄腈）氯化钯（II）和Xantphos的组合在120°C的苯甲醚溶液中提供了所需化合物以及弱碱NaOAc的最高收率。为了确保反应中的高化学选择性，催化体系和溶剂的选择被证明是重要的。富电子和缺电子的芳基溴在此反应中均能很好地发挥作用。向反应中加入1当量的碘化钠可改善缺电子的芳基溴化物的化学选择性。硫醇范围包括芳基和烷基硫醇，包括2-巯基二苯甲酮，其中通过硫羰基化和随后的McMurry偶联生成不同取代的苯并噻吩。事实证明，该方法可以适用于13 C引入噻吩环。
• Electrochemical reductive cross-coupling of acyl chlorides and sulfinic acids towards the synthesis of thioesters
  作者：Jie Xu、Fangling Lu、Linghong Sun、Mingna Huang、Jianwei Jiang、Ke Wang、Dandan Ouyang、Lijun Lu、Aiwen Lei

  DOI：10.1039/d2gc02424a

  日期：——

  used an electrochemical reduction method to obtain thiyl radicals from sulfinic acids. In a simple undivided cell, various acyl chlorides and sulfinic acids were compatible, generating 40 examples of the desired thioesters in up to 95% yields. Preliminary mechanism studies suggested that the formation of thiyl radical species from sulfinic acid proceeded via multiple steps of a single electron transfer

  C-S键的构建是合成化学、药物化学和材料化学中的一个重要过程。硫醇通常用作提供 S 源的起始材料。然而，它们难闻的气味和毒性促使我们寻找替代品。在这种情况下，我们使用电化学还原方法从亚磺酸中获得硫自由基。在一个简单的未分裂池中，各种酰氯和亚磺酸是相容的，以高达 95% 的产率生成 40 个所需硫酯的例子。初步机制研究表明，亚磺酸形成硫自由基物质是通过单个电子转移过程的多个步骤进行的。
• Palladium-catalyzed convenient synthesis of thioesters from carboxylic acids and disulfides
  作者：Yong-Mei Xiao、Yu Zhao、Jia-Qi Li、Jin-Wei Yuan、Liang-Ru Yang、Pu Mao、Wen-Peng Mai

  DOI：10.1039/d3nj02972g

  日期：——

  A novel palladium-catalyzed convenient synthesis of thioesters from various carboxylic acids and disulfides has been developed. Both aryl and alkyl carboxylic acids are capable of coupling with diaryl or dialkyl disulfides to afford the desirable thioesters in moderate to good yields. This methodology features easy accessibility of starting materials and a broad substrate scope, providing a practical

  开发了一种新型的钯催化的由各种羧酸和二硫化物便捷合成硫酯的方法。芳基和烷基羧酸都能够与二芳基或二烷基二硫化物偶联，以中等至良好的产率提供所需的硫酯。该方法的特点是起始原料易于获取且底物范围广泛，为硫酯合成提供了一条实用的路线，无需有毒硫醇或CO气体。
• Nickel‐Catalyzed Synthesis of Thioesters from Amides and Disulfides
  作者：Wen‐Peng Mai、Yu Zhao、Ming‐Xiu Lv、Wan‐Ru Zhang、Yong‐Mei Xiao、Jin‐Wei Yuan、Liang‐Ru Yang

  DOI：10.1002/ejoc.202400026

  日期：2024.3.25

  A novel nickel-catalyzed practical and simple synthesis of thioesters from amides and disulfides has been developed. Diverse substituted aromatic amides are capable of coupling with diaryl or dialkyl disulfides via C−N/S−S cleavage to produce the desirable thioesters in moderate to good yields. This procedure features cheap metals, novel and easily preparative substrates, providing a simple and practical

  开发了一种新型的镍催化的、实用且简单的由酰胺和二硫化物合成硫酯的方法。多种取代的芳香酰胺能够通过 CN/S-S 裂解与二芳基或二烷基二硫化物偶联，以中等至良好的产率产生所需的硫酯。该方法具有廉价的金属、新颖且易于制备的底物的特点，提供了一种简单实用的方法来获得各种硫酯，而无需有毒的硫醇或CO气体。
• Palladium-Catalyzed Thiocarbonylation of Iodoarenes with Thiols in Phosphonium Salt Ionic Liquids
  作者：Hong Cao、Laura McNamee、Howard Alper

  DOI：10.1021/jo800287s

  日期：2008.5.1

  Trihexyl(tetradecyl)phosphonium hexafluorophosphate, a phosphonium salt ionic liquid (PSIL) is a particularly effective general reaction media for the Pd-catalyzed carbonylation reaction of iodoarenes and thiols to form thioesters. Recycling of the ionic liquid containing active Pd-catalyst was also demonstrated.