1-(4-chlorophenyl)-2-(2-(methylthio)phenoxy)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-chlorophenyl)-2-(2-(methylthio)phenoxy)ethanone
• 英文别名: 1-(4-Chlorophenyl)-2-(2-methylsulfanylphenoxy)ethanone
• 化学式: C₁₅H₁₃ClO₂S
• mdl: MFCD19023697
• 分子量: 292.786
• InChiKey: RIKHBVBIOISNTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基茴香硫醚 、 2'-溴-4-氯苯乙酮 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 以75%的产率得到1-(4-chlorophenyl)-2-(2-(methylthio)phenoxy)ethanone
  参考文献：
  名称：

  Structure–activity relationship of antileishmanials neolignan analogues

  摘要：

  Twenty-two synthetic analogues of neolignans comprising beta-ketoethers and beta-ketosulfides were obtained from condensation reactions among beta-bromoketones and phenols or thiophenols, respectively, in basic solutions, and assayed in vitro for activity against intracellular Leishmania amazonensis and Leishmania donovani amastigotes, the causative agents of cutaneous and visceral leishmaniasis. The highest selective activity was found for compounds with sulfur bridges, whereas beta-ketosulphoxides and beta-ketosulphones had significantly less growth inhibitory activity. Compounds 2-[(4-chlorophenyl)thio]propan-1-one and 1-(3,4-dimethoxy)2-[(4-methylphenyl)thio]propan-1-one were the most potent, inhibiting the growth parasite species by over 90% at microgram/mL, but only compound 1-(3,4-dimethoxy)-2-[(4-methylphenyl)thio]propan-1-one was selectively toxic to the parasites. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.016

文献信息

• Three-Component Coupling Reaction Triggered by Insertion of Arynes into the S═O Bond of DMSO
  作者：Feng-Lei Liu、Jia-Rong Chen、You-Quan Zou、Qiang Wei、Wen-Jing Xiao

  DOI：10.1021/ol501638x

  日期：2014.7.18

  An unprecedented three-component coupling reaction of arynes, α-bromo carbonyl compounds, and DMSO triggered by insertion of arynes into the S═O bond of DMSO has been developed. The reaction can generate a wide range of multisubstituted aryl methyl thioethers in good yields, wherein DMSO serves as both methylthiolation reagent and oxygen source.

  通过将芳烃插入DMSO的S═O键引发的芳烃，α-溴代羰基化合物和DMSO的空前三组分偶联反应已得到开发。该反应可以高收率产生多种多取代的芳基甲基硫醚，其中DMSO既用作甲基硫醇化试剂又用作氧源。
• Structure–activity relationship of antileishmanials neolignan analogues
  作者：Mário Aveniente、Eduardo F. Pinto、Lourivaldo S. Santos、Bartira Rossi-Bergmann、Lauro E.S. Barata

  DOI：10.1016/j.bmc.2007.08.016

  日期：2007.12

  Twenty-two synthetic analogues of neolignans comprising beta-ketoethers and beta-ketosulfides were obtained from condensation reactions among beta-bromoketones and phenols or thiophenols, respectively, in basic solutions, and assayed in vitro for activity against intracellular Leishmania amazonensis and Leishmania donovani amastigotes, the causative agents of cutaneous and visceral leishmaniasis. The highest selective activity was found for compounds with sulfur bridges, whereas beta-ketosulphoxides and beta-ketosulphones had significantly less growth inhibitory activity. Compounds 2-[(4-chlorophenyl)thio]propan-1-one and 1-(3,4-dimethoxy)2-[(4-methylphenyl)thio]propan-1-one were the most potent, inhibiting the growth parasite species by over 90% at microgram/mL, but only compound 1-(3,4-dimethoxy)-2-[(4-methylphenyl)thio]propan-1-one was selectively toxic to the parasites. (C) 2007 Elsevier Ltd. All rights reserved.