3-[(4-甲氧苯基)硫烷基]苯甲酸 | 128950-14-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 3-[(4-甲氧苯基)硫烷基]苯甲酸
• 英文名称: 4-<(3-carboxyphenyl)thio>anisole
• 英文别名: 3-[(4-methoxyphenyl)sulfanyl]benzoic acid；3-(4'-methoxyphenyl)sulfanylbenzoic acid；3-(4-methoxyphenyl)sulfanylbenzoic acid；3-(4-methoxyphenylsulfanyl)benzoic acid；3-(p-methoxyphenyl)sulfanylbenzoic acid；3-(4-methoxyphenylthio)benzoic acid
• CAS: 128950-14-1
• 化学式: C₁₄H₁₂O₃S
• 分子量: 260.313
• InChiKey: GDTFNFKJJCBOJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(4-甲氧苯基)硫烷基]苯甲酸 在 硫酸 、 吡啶盐酸盐 作用下， 反应 100.0h， 生成 4-<<3-(ethoxycarbonyl)phenyl>thio>phenol
  参考文献：
  名称：

  Benzophenone dicarboxylic acid antagonists of leukotriene B4. 1. Structure-activity relationships of the benzophenone nucleus

  摘要：

  A series of lipophilic benzophenone dicarboxylic acid derivatives was prepared which inhibited the binding of the potent chemotaxin leukotriene B4 to its receptor(s) on intact human neutrophils. With a radioligand-binding assay as a measure of receptor affinity, a structure-activity relationship for this series was investigated. Both acidic residues were required for receptor-binding activity. The relative orientation of the two acidic groups was important for optimal binding. Replacement of the carbonyl group of the benzophenone with a variety of polar and nonpolar linking groups led to only small changes in binding affinity, indicating the linking group may not be involved in receptor recognition. Further structure-activity relationships within this series are reported in an accompanying paper.

  DOI：

  10.1021/jm00172a019
• 作为产物：
  描述：

  4-甲氧基苯硫酚 、 3-氯苯甲酸 在 palladium diacetate 、 CyPF-t-Bu sodium t-butanolate 作用下， 以 乙二醇二甲醚 为溶剂， 以74%的产率得到3-[(4-甲氧苯基)硫烷基]苯甲酸
  参考文献：
  名称：

  用于芳基氯化物与硫醇的钯催化偶联的高效且具有官能团耐受性的催化剂。

  摘要：

  据报道，芳基氯化物与强结合双膦CyPF-tBu配体（1）的钯配合物催化的脂族和芳族硫醇的交叉偶联反应。由配体1的配合物催化的大多数反应发生的周转数比先前催化剂的周转数高两个数量级。反应以优异的收率，广泛的范围和对官能团的高耐受性进行。还描述了在低负载量下衍生自其他Josiphos型配体以及其他结构类型的配体的芳基卤化物与硫醇的偶联。

  DOI：

  10.1002/chem.200600949

文献信息

• Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol
  作者：Yajun Liu、Jihye Kim、Heesun Seo、Sunghyouk Park、Junghyun Chae

  DOI：10.1002/adsc.201400941

  日期：2015.7.6

  single‐step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2‐ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high

  利用铜（II）催化剂和1,2-乙二硫醇开发了一种高效的过渡金属催化的从芳基卤化物单步合成芳基硫醇的方法。关键特征是使用现成的试剂，简单的操作以及相对温和的反应条件。该新协议显示了广泛的底物范围，具有出色的官能团相容性。由芳基卤化物直接以高收率制备各种芳基硫醇。此外，芳基硫醇原位用于合成更高级的分子，例如二芳基硫醚和苯并噻吩。
• A General, Efficient, and Functional-Group-Tolerant Catalyst System for the Palladium-Catalyzed Thioetherification of Aryl Bromides and Iodides
  作者：Manuel A. Fernández-Rodríguez、John F. Hartwig

  DOI：10.1021/jo802594d

  日期：2009.2.20

  reaction of aryl bromides and iodides with aliphatic and aromatic thiols catalyzed by palladium complexes of the bisphosphine ligand CyPF-tBu (1) is reported. Reactions occur in excellent yields, broad scope, high tolerance of functional groups, and with turnover numbers that exceed those of previous catalysts by 2 or 3 orders of magnitude. These couplings of bromo- and iodoarenes are more efficient than

  报道了由双膦配体 CyPF- t Bu ( 1 )的钯配合物催化的芳基溴化物和碘化物与脂肪族和芳香族硫醇的交叉偶联反应。反应以优异的产率、广泛的范围、高的官能团耐受性以及比以前催化剂高出 2 或 3 个数量级的周转数发生。这些溴代芳烃和碘代芳烃的偶联比氯芳烃的相应反应更有效，并且可以在较少的催化剂负载和/或更温和的反应条件下进行。因此，以前在芳基氯偶联中报道的范围和官能团耐受性的限制现在得到了克服。
• A General and Long-Lived Catalyst for the Palladium-Catalyzed Coupling of Aryl Halides with Thiols
  作者：Manuel A. Fernández-Rodríguez、Qilong Shen、John F. Hartwig

  DOI：10.1021/ja0580340

  日期：2006.2.1

  general catalytic system for the coupling of aryl halides and sulfonates with thiols based on the use of the CyPF-t-Bu ligand (1) is reported. The reactions catalyzed by complexes of 1 occur in excellent yields with broad scope and exhibit extraordinary turnover numbers and high tolerance of functional groups. Turnover numbers usually exceed those of previous catalysts by 2 or 3 orders of magnitude.

  报道了基于使用 CyPF-t-Bu 配体 (1) 将芳基卤化物和磺酸盐与硫醇偶联的通用催化系统。由 1 的配合物催化的反应以优异的产率和广泛的范围发生，并表现出非凡的转换数和高官能团耐受性。营业额通常比以前的催化剂高出 2 或 3 个数量级。此外，首次报道了芳基甲苯磺酸酯与烷烃硫醇形成芳基硫化物的反应。最后，使用硫化氢替代物完成了由两种溴芳烃合成二芳基硫化物。
• Synthesis and cytotoxicity of novel artemisinin derivatives containing sulfur atoms
  作者：Cang-Cang Xu、Juan-Juan Wu、Tao Xu、Chun-Hua Yao、Bo-Yang Yu、Ji-Hua Liu

  DOI：10.1016/j.ejmech.2016.08.015

  日期：2016.11

  Ten novel artemisinin derivatives containing sulfur atoms were designed and synthesized and their structures were confirmed by 1H NMR, 13C NMR and HRMS technologies in this study. All compounds were reported for the first time. The in vitro cytotoxicity against PC-3, SGC-7901, A549 and MDA-MB-435s cancer cell lines was evaluated by MTT assay. Compounds 4a and 4f displayed potent antitumor activity

  本研究设计合成了10种含硫原子的新型青蒿素衍生物，并通过1 H NMR、13 C NMR和HRMS技术对其结构进行了确证。所有化合物均为首次报道。在体外对PC-3细胞毒性，SGC-7901，A549和MDA-MB-435S细胞系通过MTT测定评价。化合物4a和4f对 PC-3、SGC-7901 和 A549 细胞显示出有效的抗肿瘤活性，IC 50范围为 1.6 至 30.5 μM，与 5-FU 的值相比（IC 50为 6.8 至 42.5 μM）。化合物4a和4f与正常人肝 L-02 细胞相比，对人肺癌 A549 细胞显示出高度特异性，选择性指数分别为 16.1 和 50.1。我们有希望的发现表明化合物4a和4f可以作为进一步研究的潜在先导化合物。
• A General Palladium-Catalyzed Coupling of Aryl Bromides/Triflates and Thiols
  作者：Takahiro Itoh、Toshiaki Mase

  DOI：10.1021/ol047996t

  日期：2004.11.1

  We have developed an efficient palladium-catalyzed carbon-sulfur bond formation reaction of aryl bromides, triflates, and activated aryl chloride. Using this protocol, we have shown tolerance to a wide variety of aryl thiols and alkyl thiols that can also be used as sulfide equivalents. [reaction: see text]

  我们已经开发了一种有效的钯催化的芳基溴化物，三氟甲磺酸酯和活化的芳基氯的碳硫键形成反应。使用此协议，我们显示了对多种芳基硫醇和烷基硫醇的耐受性，这些芳族硫醇和烷基硫醇也可用作硫化物的等同物。[反应：看文字]