S-thiophen-2-yl ethanethioate | 87947-35-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: S-thiophen-2-yl ethanethioate
• 英文别名: Thiophene-2-thiol, S-acetyl-
• CAS: 87947-35-1
• 化学式: C₆H₆OS₂
• 分子量: 158.245
• InChiKey: JCCFKXLGGNMORV-UHFFFAOYSA-N

物化性质

• 沸点：
  74-80 °C(Press: 1.3 Torr)
• 密度：
  1.2474 g/cm3
• 保留指数：
  1264.2

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-thiophen-2-yl ethanethioate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 2-噻吩硫醇
  参考文献：
  名称：

  Organic compounds and their use as pharmaceuticals

  摘要：

  公式为##STR1##的药用活性化合物，其中R.sup.1为C.sub.1-4烷硫基，C.sub.1-4烷基亚砜基或C.sub.1-4烷基磺酰基，R.sup.2为C.sub.1-4烷基，R.sup.3为C.sub.1-4烷基或C.sub.2-4烯基，X为(i) --(CH.sub.2).sub.n N(R.sup.4).sub.2，其中每个独立的R.sup.4为C.sub.1-4烷基，C.sub.2-4烯基或可选择地取代的C.sub.6 H.sub.5 CH.sub.2 --，n为1、2或3，或(ii)含有一个或两个氮原子并直接连接到酰胺氮或通过C.sub.1-3烷基链连接的5-至8-成员脂环基；及其盐。

  公开号：

  US05041461A1
• 作为产物：
  描述：

  双(2-噻吩基)二硫醚 、 乙酸酐 在 rongalite 、 cesium fluoride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以96%的产率得到S-thiophen-2-yl ethanethioate
  参考文献：
  名称：

  A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite®

  摘要：

  Rongalite (R) promotes cleavage of diaryl disulfides generating chalcogenolate anions that then undergo facile acylation with anhydrides in the presence of CsF to afford thioesters (3) with good to excellent yields. By using the present protocol, 5-arylthio-5-oxopentanoic acid (4) can be facilely prepared. The important features of the methodology are broad substrate scope, simple operation, and no requirement for metal catalysts. It is noteworthy that acylations of diphenyl diselane with anhydrides are also conducted smoothly to afford selenoesters (5) in good yields under the standard conditions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.023

文献信息

• NiNP@rGO Nanocomposites as Heterogeneous Catalysts for Thiocarboxylation Cross-Coupling Reactions
  作者：Marco Bandini、Lorenzo Lombardi、Raffaello Mazzaro、Massimo Gazzano、Alessandro Kovtun、Vittorio Morandi、Giulio Bertuzzi

  DOI：10.1055/a-1669-0944

  日期：2022.3

  and spectroscopic (ICP-EOS, XPS) analysis tools. The metal composite was effectively employed in the unprecedented heterogeneously Ni-assisted cross-coupling reaction of aryl/vinyl iodides and thiocarboxylates. A range of sulfur-containing aryl as well as vinyl derivatives (15 examples) was achieved in high yields (up to 82%), under mild reaction conditions, and with wide functional group tolerance

  制备了一种新型的无配体镍纳米颗粒支撑在 rGO 上（平均粒径分布 d = 9 ± 3 nm），并通过形态学 (Fe-SEM)、结构学 (P-XRD、HR-TEM) 和光谱学进行了充分表征(ICP-EOS, XPS) 分析工具。该金属复合物有效地用于芳基/乙烯基碘化物和硫代羧酸盐的前所未有的非均相 Ni 辅助交叉偶联反应。在温和的反应条件和广泛的官能团耐受性下，以高产率（高达 82%）获得了一系列含硫芳基和乙烯基衍生物（15 个实例）。
• Rhodium-catalyzed denitrogenative <i>gem</i>-difunctionalization of pyridotriazoles with thioesters: formal carbene insertion into C(O)–S bonds
  作者：Zhe Gao、Di Jiang、Bin Li、Baiquan Wang

  DOI：10.1039/d1cc06041d

  日期：——

  A formal carbene insertion into C(O)–S bonds to access α-quaternary pyridines was achieved via a rhodium(II)-catalyzed in situ formation of sulfonium ylides from pyridotriazoles with thioesters followed by acyl group migration. This protocol has enabled an efficient denitrogenative gem-acylthiolation of pyridotriazoles to incorporate an acyl, pyridyl, and sulfur-substituted quaternary carbon center

  通过铑( II )催化从吡啶三唑与硫酯原位形成锍叶立德，随后酰基迁移，实现了正式的卡宾插入C(O)-S键以接近α-季吡啶。该协议使吡啶三唑的高效脱氮宝石-酰基硫醇化能够结合酰基、吡啶基和硫取代的季碳中心，具有高选择性、广泛的底物范围和良好的官能团耐受性。
• Synthesis, computational and electrochemical characterization of a family of functionalized dimercaptothiophenes for potential use as high-energy cathode materials for lithium/lithium-ion batteries
  作者：Yasuyuki Kiya、Jay C. Henderson、Geoffrey R. Hutchison、Héctor D. Abruña

  DOI：10.1039/b707235j

  日期：——

  We present a family of a novel class of organosulfur compounds based on dimercaptothiophene and its derivatives, with a variety of functional groups (electron-donating or electron-withdrawing groups) and regiochemistries, designed as potential high-energy cathode materials with sufficient charge/discharge cyclability for lithium/lithium-ion rechargeable batteries. This study uses as a point of departure the electrochemical and computational understanding of the electrocatalytic effect of poly(3,4-ethylenedioxythiophene) (PEDOT) towards the redox reactions of 2,5-dimercapto-1,3,4-thiadiazole (DMcT). The effective redox potentials of these materials exhibited good correlation with the highest-occupied molecular orbital (HOMO) levels predicted via computational modeling. Furthermore, the redox reactions of all the compounds studied were electrocatalytically accelerated at PEDOT film-coated glassy carbon electrodes (GCEs), although some materials exhibited higher energy output than others. By using this approach we have identified several compounds that exhibit clear promise as potential cathode materials and have characterized the molecular interactions between the organosulfur compounds and PEDOT film surfaces involved in the electrocatalytic reactions.

  我们提出了一类基于二巯基噻吩及其衍生物的新型有机硫化合物家族，这些化合物具有多种功能团（电子供体或电子受体基团）和区域化学特性，旨在作为潜在的高能阴极材料，具备足够的充放电循环能力，以用于锂/锂离子可充电电池。本研究的出发点是对聚（3,4-亚乙基双氧噻吩）（PEDOT）在2,5-二巯基-1,3,4-噻二唑（DMcT）氧化还原反应中的电催化效应进行电化学和计算理解。这些材料的有效氧化还原电位与通过计算建模预测的最高占据分子轨道（HOMO）能级表现出良好的关联。此外，所有研究的化合物在PEDOT膜涂覆的玻碳电极（GCEs）上进行的氧化还原反应均被电催化加速，尽管某些材料的能量输出高于其他材料。通过这种方法，我们识别出了几种表现出明显潜力作为阴极材料的化合物，并表征了参与电催化反应的有机硫化合物与PEDOT膜表面之间的分子相互作用。
• 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。
• Organic componds and their use as pharmaceuticals
  申请人：LILLY S.A.

  公开号：EP0361961A1

  公开（公告）日：1990-04-04

  A pharmaceutically-active compound of the formula in which R¹ is C₁₋₄ alkylthio, C₁₋₄ alkylsulphinyl or C₁₋₄ alkylsulphonyl, R² is C₁₋₄ alkyl, R³ is C₁₋₄ alkyl or C₂₋₄ alkenyl, and X is (i) -(CH₂)nN(R⁴)₂ where each R⁴ independently is C₁₋₄ alkyl, C₂₋₄ alkenyl or optionally substituted C₆H₅CH₂-, and n is 1, 2 or 3, or (ii) a 5- to 8-membered alicyclic group containing one or two nitrogen atoms and directly attached to the amido nitrogen or attached by a C₁₋₃ alkylene chain; and salts thereof.

  一种药物活性化合物，其式如下 其中 R¹ 是 C₁₋₄ 烷硫基、C₁₋₄ 烷基亚磺酰基或 C₁₋₄ 烷基磺酰基，R² 是 C₁₋₄ 烷基，R³ 是 C₁₋₄ 烷基或 C₂₋₄ 烯基，X 是 (i) -(CH₂)nN(R⁴)₂ 其中每个 R⁴ 独立地是 C₁₋₄ 烷基、C₂₋₄烯基或任选取代的 C₆H₅CH₂-，且 n 为 1、2 或 3，或 (ii) 包含一个或两个氮原子并直接连接至氨基氮或通过 C₁₋₃亚烷基链连接的 5 至 8 元脂环基团；及其盐类。