S-(4-fluorophenyl) 4-methoxybenzothioate | 1422008-18-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S-(4-fluorophenyl) 4-methoxybenzothioate
• CAS: 1422008-18-1
• 化学式: C₁₄H₁₁FO₂S
• 分子量: 262.305
• InChiKey: SDDQDJQKWQIRJV-UHFFFAOYSA-N

物化性质

• 沸点：
  371.1±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  对氟苯硫酚 、 大茴香酸 在 4-Br-C5H4N*BH3 作用下， 以 邻二氯苯 为溶剂， 以30 %的产率得到S-(4-fluorophenyl) 4-methoxybenzothioate
  参考文献：
  名称：

  吡啶-硼烷复合物催化的硫酯化：羧酸直接转化为硫酯

  摘要：

  硫酯是一类常见的生物活性片段和合成有用的结构单元。一种有吸引力的合成方法是使用简单且实验室稳定的羧酸作为偶联伙伴。在此，我们提出了一种 4-溴吡啶-硼烷络合物作为羧酸与硫醇直接偶联的催化剂。通过这种无金属方法可以制备各种具有良好官能团相容性的硫酯。该策略的优点通过含羧酸药物的修饰得到了例证。

  DOI：

  10.1039/d4cc01326c

文献信息

• Microwave-assisted Synthesis of Thioesters from Aldehydes and Thiols in Water
  作者：Huei-Shu Jhuang、Yi-Wei Liu、Daggula Mallikarjuna Reddy、Yong-Ze Tzeng、Wei-Yu Lin、Chin-Fa Lee

  DOI：10.1002/jccs.201700045

  日期：2018.1

  We describe the synthesis of thioesters via copper‐ or iron‐catalyzed coupling of thiols with aldehydes on application of microwave irradiation. In this protocol, a variety of aliphatic and aromatic aldehydes and thiols were used, and the products were obtained in good to excellent yields.

  我们描述了在微波辐射下通过铜或铁催化的硫醇与醛的偶联反应合成硫酯。在该方案中，使用了各种脂族和芳族醛和硫醇，并以良好或优异的收率获得了产物。
• Synthesis of thioesters through copper-catalyzed coupling of aldehydes with thiols in water
  作者：Chih-Lun Yi、Yu-Ting Huang、Chin-Fa Lee

  DOI：10.1039/c3gc40946e

  日期：——

  Copper-catalyzed C–S bond formation between aldehydes and thiols in the presence of TBHP as an oxidant is described. Functional groups including chloro, trifluoromethyl, bromo, iodo, nitrile, ester and thiophene are all tolerated by the reaction conditions employed. This reaction is performed in water without the use of a surfactant. Both aryl and alkyl aldehydes couple suitably with aryl- and alkyl thiols, affording the corresponding thioesters in moderate to good yields.

  介绍了在氧化剂TBHP存在下，铜催化的醛与硫醇之间的C-S键形成反应。所采用的反应条件能够容忍包括氯、三氟甲基、溴、碘、腈、酯和噻吩在内的多种官能团。该反应在水相中进行，无需使用表面活性剂。芳基和烷基醛均能与芳基和烷基硫醇适当地耦合，以中等至良好的产率得到相应的硫酯。
• Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides
  作者：Shimin Xie、Lebin Su、Min Mo、Wang Zhou、Yongbo Zhou、Jianyu Dong

  DOI：10.1021/acs.joc.0c02328

  日期：2021.1.1

  coupling of readily available aroylhydrazides with disulfides is developed, in which oxidative expulsion of N2 overcomes the activation barrier between the carboxylic acid derivatives and the products. The reaction produces various thioesters in good to excellent yields with good functional group tolerance. In the reaction, stable and easily available aroylhydrazides are used as acyl sources and the

  通过易得的芳酰肼与二硫化物的铜催化的氧化偶联，开发了另一种硫酯化反应，其中N 2的氧化排出克服了羧酸衍生物和产物之间的活化障碍。该反应以良好的收率和优异的官能度耐受性产生了各种硫酯。在该反应中，将稳定且容易获得的芳酰基酰肼用作酰基源，并将相对无味的二硫化物用作S源。机理研究表明，铜盐与氧化剂（NH 4）2 S 2 O 8的反应 可以实现串联过程，包括去质子化，自由基介导的脱氮和CS键形成。
• Nickel-Catalyzed Metathesis between Carboxylic Acids and Thioesters: A Direct Access to Thioesters
  作者：Qiumin Xie、Anhui Wei、Ziding Liu、Qian Yan、Xiuli Zhang、Bao Gao

  DOI：10.1021/acs.orglett.3c02664

  日期：2023.9.29

  for generating thioesters from carboxylic acids and thioesters. This transformation features operational simplicity and high step-economy, wherein the −SR moiety of thioesters was smoothly transferred to carboxylic acid from thioacetates as the starting material. Various substrates with different levels of electronic nature were all applicable to this reaction, furnishing thioesters in moderate to

  我们描述了一种从羧酸和硫酯生成硫酯的独特策略。该转化具有操作简单和步骤经济性高的特点，其中硫代酯的-SR部分顺利地从硫代乙酸酯作为起始原料转移到羧酸。具有不同电子性质水平的各种底物都适用于该反应，以中等至出色的产率提供硫酯。根据初步的机理研究，酸酐中间体可能参与了本反应。
• Pd-Catalyzed Thiocarbonylation with Stoichiometric Carbon Monoxide: Scope and Applications
  作者：Mia N. Burhardt、Rolf H. Taaning、Troels Skrydstrup

  DOI：10.1021/ol400138m

  日期：2013.2.15

  A general protocol for the Pd-catalyzed thiocarbonylation of aryl iodides with stoichiometric carbon monoxide has been established employing a catalytic system composed of Pd(OAc)(2) and DPEphos with low catalyst loading (1 mol %). Both electron-rich and -deficient aryl iodides proved effective for these couplings with aryl and alkyl thiols. The choice of the metal ligands and the solvent system was crucial for the efficiency and chemoselectivity of these transformations.