S-(4-phenylbutyl) ethanethioate | 294201-60-8

• 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-phenylbutyl) ethanethioate
• 英文别名: S-acetyl 4-phenylbutanethiol；S-4-phenylbutyl thioacetate
• CAS: 294201-60-8
• 化学式: C₁₂H₁₆OS
• 分子量: 208.324
• InChiKey: KZTBTLLJFJARMK-UHFFFAOYSA-N

物化性质

• 沸点：
  313.1±21.0 °C(predicted)
• 密度：
  1.044±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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-(4-phenylbutyl) ethanethioate 在 氯磺酸 、 氢氧化钾 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 18.5h， 生成 bis[4-(4-chlorosulfonylphenyl)butyl] disulfide
  参考文献：
  名称：

  Syntheses of the Novel Acidic and Basic Ligands and Superlattice Formation from Gold Nanoparticles through Interparticle Acid–Base Interaction

  摘要：

  合成了新的酸性或碱性芳基-烷基二硫化物，具有酚、苯甲酸、苯磺酸、苯胺和苄胺基团，作为金（Au）纳米颗粒的保护剂。使用化学还原技术制备了被这些配体钝化的单分散Au纳米颗粒，并在基底上自组装成具有良好有序的六方紧密堆积（hcp）二维超晶格。我们首次展示了通过混合分别合成的酸性和碱性Au纳米颗粒，在水-有机溶剂界面形成的聚集多层Au纳米颗粒。这种薄膜与LB法和通过溶剂蒸发的传统自组装法获得的薄膜明显不同。

  DOI：

  10.1246/bcsj.77.1589
• 作为产物：
  描述：

  4-苯基丁醇 、 硫代乙酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以99%的产率得到S-(4-phenylbutyl) ethanethioate
  参考文献：
  名称：

  A New Class of Antituberculosis Agents

  摘要：

  Long-chain lipid envelopes are characteristic of mycobacteria such as those that cause tuberculosis and leprosy. Inhibition of fatty acid synthesis or elongation is a strategy demonstrated to be clinically effective against M. tuberculosis. A new class of compounds designed to inhibit the beta-ketoacyl synthase reaction of fatty acid synthesis has been developed. Of >30 compounds described, the most active were acetamides containing alkylsulfonyl substituents. Inhibitory activities were acutely sensitive to net charge, chain length, and degree of unsaturation. The most active compound 5 (alkyl = C-10) contained a single methylene spacer between the sulfone and carboxamide and exhibited an MIC of 0.75-1.5 mu g/mL, comparable to first-line antituberculosis drugs. These compounds are species-specific, exhibiting no significant activity against bacterial species other than M. tuberculosis and closely related strains. The synthesis, biological activity, and specificity of these compounds are described.

  DOI：

  10.1021/jm000149l

文献信息

• Visible-Light-Mediated Organocatalyzed Thiol–Ene Reaction Initiated by a Proton-Coupled Electron Transfer
  作者：Vitalij V. Levin、Alexander D. Dilman

  DOI：10.1021/acs.joc.9b01331

  日期：2019.6.21

  A convenient method for performing a thiol–ene reaction is described. The reaction is performed under blue-light irradiation and catalyzed by photoactive Lewis basic molecules such as acridine orange or naphthalene-fused N-acylbenzimidazole. It is believed that the process is initiated by a proton-coupled electron transfer process within the complex between the thiol and the Lewis basic catalyst.

  描述了一种进行硫醇-烯反应的简便方法。该反应在蓝光照射下进行，并由光活性的路易斯碱性分子如a啶橙或萘稠合的N-酰基苯并咪唑催化。据信该过程是由硫醇和路易斯碱性催化剂之间的配合物中的质子偶联电子转移过程引发的。
• Copper-catalyzed thiocarbonylation and thiolation of alkyl iodides
  作者：Qingqiang Tian、Rongjing Sun、Yahui Li

  DOI：10.1039/d2ob00008c

  日期：——

  the present study, an efficient Cu-catalyzed transthiolation of alkyl iodides is developed. Notably, in the presence of CO, thioesters could also be obtained with copper and cobalt as the co-catalyst. This transformation displayed good functional group tolerance and afforded thioesters or sulfides from the corresponding alkyl iodides.

  在本研究中，开发了一种有效的 Cu 催化烷基碘的转硫醇化。值得注意的是，在 CO 存在下，硫酯也可以用铜和钴作为助催化剂来获得。这种转化表现出良好的官能团耐受性，并从相应的烷基碘中得到硫酯或硫化物。
• Direct Synthesis of Thioesters from Feedstock Chemicals and Elemental Sulfur
  作者：Haidi Tang、Muliang Zhang、Yuchao Zhang、Penghao Luo、Davide Ravelli、Jie Wu

  DOI：10.1021/jacs.2c13157

  日期：2023.3.15

  available commodity chemicals is a central goal of organic synthesis. In this context, the thiol–ene click chemistry for carbon–sulfur (C–S) bond construction has found widespread applications in the synthesis of pharmaceuticals and functional materials. In contrast, the selective carbonyl thiyl radical addition to carbon–carbon multiple bonds remains underdeveloped. Herein, we report a carbonyl thiyl radical-based

  开发一种温和的、原子和步骤经济的催化策略，直接从现成的商品化学品中有效地产生增值分子是有机合成的中心目标。在这种情况下，用于碳硫（C-S）键构建的硫醇-烯点击化学已在药物和功能材料的合成中得到广泛应用。相比之下，碳-碳多重键的选择性羰基硫基自由基加成仍然不发达。在此，我们通过直接光催化氢原子转移，通过原料醛、烯烃或炔烃和元素硫的三组分偶联，报道了基于羰基硫基自由基的硫酯合成。该方法代表了传统的基于硫醇的亲核取代的正交策略，并表现出非常广泛的底物范围，从简单的商品化学品（如乙烯和乙炔）到复杂的药物分子。该协议可以很容易地扩展到硫内酯、低聚物/聚合物和硫代酸的合成。它的合成效用已通过药物依索莫德的两步合成得到证明。机理研究表明，使用元素硫来捕获酰基自由基在热力学和动力学上都是有利的，说明它在合成含硫分子方面具有巨大潜力。该协议可以很容易地扩展到硫内酯、低聚物/聚合物和硫代酸的合成。它的合成效用
• Syntheses of the Novel Acidic and Basic Ligands and Superlattice Formation from Gold Nanoparticles through Interparticle Acid–Base Interaction
  作者：Masayuki Kanehara、Yasunori Oumi、Tsuneji Sano、Toshiharu Teranishi

  DOI：10.1246/bcsj.77.1589

  日期：2004.8

  Novel acidic or basic aryl-alkyl disulfides having phenol, benzoic acid, benzenesulfonic acid, aniline, and benzylamine groups were synthesized as protective agents for gold (Au) nanoparticles. Monodisperse Au nanoparticles passivated by these ligands were prepared using a chemical reduction technique, and self-assembled into well-ordered hexagonal close-packed (hcp) 2D superlattices on the substrate. We also present, for the first time, the formation of an aggregated multilayer of Au nanoparticles at a water–organic solvent interface by mixing separately synthesized acidic and basic Au nanoparticles. This film was definitely different from those obtained by the LB method and the conventional self-assembly method through solvent evaporation.

  合成了新的酸性或碱性芳基-烷基二硫化物，具有酚、苯甲酸、苯磺酸、苯胺和苄胺基团，作为金（Au）纳米颗粒的保护剂。使用化学还原技术制备了被这些配体钝化的单分散Au纳米颗粒，并在基底上自组装成具有良好有序的六方紧密堆积（hcp）二维超晶格。我们首次展示了通过混合分别合成的酸性和碱性Au纳米颗粒，在水-有机溶剂界面形成的聚集多层Au纳米颗粒。这种薄膜与LB法和通过溶剂蒸发的传统自组装法获得的薄膜明显不同。
• A New Class of Antituberculosis Agents
  作者：Paul B. Jones、Nikki M. Parrish、Todd A. Houston、Anthony Stapon、Niharika P. Bansal、James D. Dick、Craig A. Townsend

  DOI：10.1021/jm000149l

  日期：2000.8.1

  Long-chain lipid envelopes are characteristic of mycobacteria such as those that cause tuberculosis and leprosy. Inhibition of fatty acid synthesis or elongation is a strategy demonstrated to be clinically effective against M. tuberculosis. A new class of compounds designed to inhibit the beta-ketoacyl synthase reaction of fatty acid synthesis has been developed. Of >30 compounds described, the most active were acetamides containing alkylsulfonyl substituents. Inhibitory activities were acutely sensitive to net charge, chain length, and degree of unsaturation. The most active compound 5 (alkyl = C-10) contained a single methylene spacer between the sulfone and carboxamide and exhibited an MIC of 0.75-1.5 mu g/mL, comparable to first-line antituberculosis drugs. These compounds are species-specific, exhibiting no significant activity against bacterial species other than M. tuberculosis and closely related strains. The synthesis, biological activity, and specificity of these compounds are described.