S-phenyl pyridine-3-carbothioate | 28122-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: S-phenyl pyridine-3-carbothioate
• CAS: 28122-96-5
• 化学式: C₁₂H₉NOS
• 分子量: 215.276
• InChiKey: UCOIXCWIEHXKGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-phenyl pyridine-3-carbothioate 在 bis(1,5-cyclooctadiene)nickel (0) 、 三环己基膦 作用下， 以 甲苯 为溶剂， 以66%的产率得到3-phenylthiopyridine
  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：

  二苯二硫醚 在 tetrabutylammonium decatungstate 、 碘 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 S-phenyl pyridine-3-carbothioate
  参考文献：
  名称：

  CO‐Boosted Protocol for the Photocatalytic C‐H Thiolation of Aldehydes Using Phenylthiobenzenesulfonate

  摘要：

  The formyl C‐H thiolation of aldehydes using thiosulfonates using the decatungstate anion as a photocatalyst is reported. Using this photocatalytic protocol, both aromatic and aliphatic thioesters can be synthesized in good yields. The transformation consists of a cascade of double SH2 reactions, HAT and an ArS group transfer, and the yields are improved when the reaction is carried out in a CO atmosphere, which serves to limit the extent of decarbonylation acyl radicals that are generated in the reaction.

  DOI：

  10.1002/ejoc.202400138

文献信息

• Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP
  作者：Shuang-Qi Tang、Jacques Bricard、Martine Schmitt、Frédéric Bihel

  DOI：10.1021/acs.orglett.9b00031

  日期：2019.2.1

  identified for use in Fukuyama cross-coupling reactions. Suitable for storage under air, the POxAP precatalyst allowed reaction between thioesters and organozinc reagents with turnover numbers of ∼90000. A series of 23 ketones were obtained with yields ranging from 53 to 99%. As proof of efficacy, an alternative approach was developed for the synthesis of a key precursor of the natural product isoprekinamycin

  确定了一种有效且用户友好的钯（II）预催化剂POxAP（后氧化加成预催化剂）可用于福山交叉偶联反应。POxAP预催化剂适合在空气中储存，它可使硫代酯与有机锌试剂之间的反应发生反应，其周转数约为90000。获得了一系列23种酮，产率为53％至99％。作为功​​效的证明，开发了另一种方法来合成天然产物异普瑞霉素的关键前体。
• Photocatalytic Phosphine-Mediated Thioesterification of Carboxylic Acids with Disulfides
  作者：Junqi Su、Aobo Chen、Guofeng Zhang、Ziyu Jiang、Jiannan Zhao

  DOI：10.1021/acs.orglett.3c03249

  日期：2023.11.10

  Herein, a practical and effective synthesis of thioesters from readily available carboxylic acids and odorless disulfides was developed under photocatalytic conditions. This approach involves phosphoranyl radical-mediated fragmentation to generate acyl radicals and allows for incorporation of both S atoms of the disulfides into the desired products. In addition to batch reactions, a continuous-flow

  在此，在光催化条件下开发了一种实用且有效的由容易获得的羧酸和无味二硫化物合成硫酯的方法。该方法涉及正膦基自由基介导的断裂以产生酰基自由基，并允许将二硫化物的两个S原子掺入所需的产物中。除了间歇反应外，还采用了连续流反应器，能够实现克级的快速硫酯合成。还展示了初步实验机制研究和 dalcetrapib 的快速合成。
• Nicotinsäure-phenolester mit antimykotischer und hyperämisierender Wirksamkeit
  作者：Helmut Zinner、Heinz Fiedler

  DOI：10.1002/ardp.19582910704

  日期：——
• Pt-catalyzed regio- and stereoselective pyridylthiolation of terminal alkynes
  作者：Takayoshi Hirai、Hitoshi Kuniyasu、Nobuaki Kambe

  DOI：10.1016/j.tetlet.2004.11.023

  日期：2005.1

  Three-component cross-coupling, reactions among 3-iodopyridynes, terminal alkynes and ArSK took place in the presence of Pt-catalyst to give pyridine derivatives with conjugated vinyl groups in moderate yields. (C) 2004 Elsevier Ltd. All rights reserved.
• Dess–Martin periodinane mediated synthesis of thioesters from aldehydes
  作者：Sunita B. Bandgar、B.P. Bandgar、B.L. Korbad、S.S. Sawant

  DOI：10.1016/j.tetlet.2006.12.024

  日期：2007.2

  Dess-Martin periodinane (DMP) mediated efficient synthesis of thioesters from the corresponding aldehydes under mild conditions is described. (c) 2007 Elsevier Ltd. All rights reserved.