ethyl (4-methoxyphenyl) sulfide | 7205-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (4-methoxyphenyl) sulfide
• 英文别名: ethyl(4-methoxyphenyl)sulfane；4-methoxyphenyl ethyl sulfide；1-(Ethylsulfanyl)-4-methoxybenzene；1-ethylsulfanyl-4-methoxybenzene
• CAS: 7205-58-5
• 化学式: C₉H₁₂OS
• mdl: MFCD11617692
• 分子量: 168.26
• InChiKey: JOTUDFBFCFFMNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (4-methoxyphenyl) sulfide 在 氢溴酸 、 溶剂黄146 作用下， 生成 4-(乙硫基)苯酚
  参考文献：
  名称：

  Assessing the Impact of Differential Measurement Error on Estimates of Fine Particle Mortality

  摘要：

  In air pollution epidemiology, error in measurements of correlated pollutants has been advanced as a reason to distrust regressions that find statistically significant weak associations. Much of the related debate in the literature and elswhere has been qualitative. To promote quantitative evaluation of such errors, this paper develops an air pollution time-series model based on correlations among unit-normal variables. Assuming there are no other sources of bias present, the model shows the expected amount of relative bias in the regression coefficients df a bivariate regression of coarse and fine particulate matter measurements on daily mortality. The model only requires information on instrumental error and spatial variability, along with the observed regression coefficients and information on the true fine-course correlation. Analytical results show that if one pollutant is truly more harmful than the other, then it must be measured more precisely than the other in order not to bias the ratio of the fine and course regression coefficients. Utilizing published data, a case study of the Harvard Six-Cities study illustrates use of the model and emphasizes the need for data on spatial variability across the study area. Current epidemiology time-series regressions can use this model to address the general concern of correlated pollutants with differing measurement errors.

  DOI：

  10.1080/10473289.2000.10463988
• 作为产物：
  描述：

  1,4-二氯苯 在 sodium 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 ethyl (4-methoxyphenyl) sulfide
  参考文献：
  名称：

  Simple Syntheses of Aryl Alkyl Thioethers and of Aromatic Thiols from Unactivated Aryl Halides and Efficient Methods for Selective Dealkylation of Aryl Alkyl Ethers and Thioethers

  摘要：

  DOI：

  10.1055/s-1983-30501
• 作为试剂：
  描述：

  2-Chloro-2-(4-trifluoromethyl-phenyl)-2λ⁴-[1,2]oxaselenolane 在 ethyl (4-methoxyphenyl) sulfide 作用下， 以 氯仿 为溶剂， 反应 96.0h， 生成 3-(4-Trifluoromethyl-phenylselanyl)-propan-1-ol
  参考文献：
  名称：

  Reactivity of Chlorooxachalcogenuranes: Oxidation of Sulfides to Sulfoxides Using Chlorooxaselenuranes

  摘要：

  The transformation of chloro between chlorooxachalcogenuranes 3 and chalcogenides 4 is described. The oxidative ability of chlorooxachalcogenuranes has been compared. Selenuranes 3a, b have been found to be good reagents for selective oxidation of sulfides to sulfoxides under mild conditions.

  DOI：

  10.1080/00397910008087115

文献信息

• Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
  作者：Tristan Delcaillau、Philip Boehm、Bill Morandi

  DOI：10.1021/jacs.1c00529

  日期：2021.3.17

  We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications

  我们描述了芳基腈和芳基硫醚之间的新官能团复分解。催化系统镍/dcype 对于实现这种完全可逆的转化，以良好的收率至关重要。此外，不含氰化物和硫醇的反应显示出高官能团耐受性和商业分子后期衍生化的高效率。最后，合成应用证明了它在多步合成中的多功能性和实用性。
• C–H Alkenylation of Heteroarenes: Mechanism, Rate, and Selectivity Changes Enabled by Thioether Ligands
  作者：Bradley J. Gorsline、Long Wang、Peng Ren、Brad P. Carrow

  DOI：10.1021/jacs.7b03887

  日期：2017.7.19

  catalytic intermediate in these reactions may also account for unusual catalyst-controlled site selectivity wherein C–H alkenylation of five-atom heteroarenes can occur under electronic control with thioether ligands even when this necessarily involves reaction at a more hindered C–H bond. The thioether effect also enables short reaction times under mild conditions for many O-, S-, and N-heteroarenes (55 examples)

  已确定硫醚辅助配体可以大大促进O-，S-和N的C–H烯基化-杂芳烃。动力学数据表明，硫醚-Pd催化的反应比经典的无配体系统快800倍之多。此外，机理研究表明，C–H键的裂解是限制周转的步骤，硫醚配位时的速率加速与该关键步骤从中性途径向阳离子途径的变化相关。在这些反应中形成阳离子型，低配位的催化中间体也可能说明了催化剂控制位点的异常，其中五原子杂芳烃的CH链烯基化可以在硫代配体的电子控制下发生，即使这必然涉及在更阻碍了CH键的键合。硫醚效应还使得许多O-，S-和N-杂芳烃（55个实例），包括晚期药物衍生化的实例。
• Site-Selective C−S Bond Formation at C−Br over C−OTf and C−Cl Enabled by an Air-Stable, Easily Recoverable, and Recyclable Palladium(I) Catalyst
  作者：Thomas Scattolin、Erdem Senol、Guoyin Yin、Qianqian Guo、Franziska Schoenebeck

  DOI：10.1002/anie.201806036

  日期：2018.9.17

  Computational, spectroscopic, X‐ray, and reactivity data support dinuclear PdI catalysis to be operative. Contrary to air‐sensitive Pd0, the active PdI species was easily recovered in the open atmosphere and subjected to multiple rounds of recycling.

  该报告将新兴的 Pd 催化作用扩展到碳杂原子，即 C−S 键形成。虽然 Pd 0催化方案可能会遇到有毒的硫化物结合的非循环中间体的形成和缺乏选择性的问题，但机械上多样化的 Pd 催化概念规避了这些挑战，并允许 C−S 键形成（S-芳基和 S-烷基） ）多种芳基卤化物。在 C−Cl 和 C−OTf 存在下，C−Br 位点的位点选择性硫醇化是以一般且先验可预测的方式实现的。计算、光谱、X 射线和反应性数据支持双核 Pd 催化是有效的。与空气敏感的 Pd 0相反，活性 Pd 物种很容易在大气中回收并进行多轮回收。
• Efficient and Highly Selective Oxidation of Sulfides to Sulfoxides in the Presence of an Ionic Liquid Containing Hypervalent Iodine
  作者：Weixing Qian、Lin Pei

  DOI：10.1055/s-2006-933109

  日期：——

  A mild, efficient, highly selective, and environmentally friendly oxidation of sulfides to sulfoxides with a recyclable ion-supported hypervalent iodine reagent has been developed. This reaction is tolerant of hydroxyl, nitrile, methoxy, carbon-carbon double bonds, and ester functionalities. Aliphatic and aromatic sulfides are selectively oxidized to the corresponding sulfoxides at room temperature

  已经开发出一种温和、高效、高选择性和环境友好的硫化物氧化法，使用可回收的离子负载高价碘试剂将硫化物氧化为亚砜。该反应耐受羟基、腈、甲氧基、碳-碳双键和酯官能团。脂肪族和芳香族硫化物在室温下以极好的收率被选择性氧化成相应的亚砜。
• Discovery of carboxyl-containing biaryl ureas as potent RORγt inverse agonists
  作者：Nannan Sun、Yafei Huang、Mingcheng Yu、Yunpeng Zhao、Ji-An Chen、Chenyu Zhu、Meiqi Song、Huimin Guo、Qiong Xie、Yonghui Wang

  DOI：10.1016/j.ejmech.2020.112536

  日期：2020.9

  GSK805 (1) is a potent RORγt inverse agonist, but a drawback of 1 is its low solubility, leading to a limited absorption in high doses. We have explored detailed structure-activity relationship on the amide linker, biaryl and arylsulfonyl moieties of 1 trying to improve solubility while maintaining RORγt activity. As a result, a novel series of carboxyl-containing biaryl urea derivatives was discovered

  GSK805（1）是一种强效RORγt反向激动剂，但缺点1是它的低溶解度，从而导致在高剂量有限的吸收。我们已经探索了1的酰胺连接基，联芳基和芳基磺酰基部分的详细结构-活性关系，试图在保持RORγt活性的同时提高溶解度。结果，发现了一系列新颖的含羧基联芳基脲衍生物，作为具有改进的类药物性质的有效RORγt反向激动剂。化合物3i显示了强大的RORγt抑制活性和亚型选择性，在RORγFRET分析中的IC 50为63.8 nM，在基于细胞的RORγ-GAL4启动子报告子分析中为85 nM。合理的3i抑制活性在小鼠Th17细胞分化试验中也获得了抑制（在0.3μM时抑制76％）。此外，与1相比，3i在pH 7.4时具有大大改善的水溶解度，表现出体面的小鼠PK曲线，并在咪喹莫特诱导的牛皮癣小鼠模型中表现出一定的体内功效。

表征谱图