8-(4'-chlorothiophenoxy)propiophenone | 59919-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-(4'-chlorothiophenoxy)propiophenone
• 英文别名: 2-(4-chlorophenylthio)propiophenone；2-(4-Chlorophenyl)sulfanyl-1-phenylpropan-1-one
• CAS: 59919-16-3
• 化学式: C₁₅H₁₃ClOS
• mdl: MFCD03361633
• 分子量: 276.787
• InChiKey: NZXWVKZAUHOQGA-UHFFFAOYSA-N

物化性质

• 沸点：
  201-203 °C(Press: 6 Torr)
• 密度：
  1.1999 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 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：

  8-(4'-chlorothiophenoxy)propiophenone 在 IF₅-5CH₂Cl₂ 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以64%的产率得到3-(4-chlorophenylthio)-2,2,3-trifluoro-1-phenylpropan-1-one
  参考文献：
  名称：

  Polyfluorination Using IF₅

  摘要：

  The polyfluorination of alpha-(arylthio)carbonyl compounds was achieved by a successive application of polyfluorination using IF5, Friedel Crafts arylation, and desulfurizing fluorination using IF5. Three to six fluorine atoms were selectively introduced to the carbons located between the aromatic ring and the carbonyl group.

  DOI：

  10.1021/jo101672g
• 作为产物：
  描述：

  2-溴苯丙酮 、 4-氯苯硫酚 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 7.0h， 以78%的产率得到8-(4'-chlorothiophenoxy)propiophenone
  参考文献：
  名称：

  来自 Virola 物种和合成类似物的新木脂素的抗利什曼原虫活性

  摘要：

  Surinamensin，一种从 Virola surinamensis 中分离的新木脂素，3,4,5-trimethoxy-8-[2',6'-dimethoxy-4'-(E)-propenylphenoxy]-phenylpropane，一种从 Virola pavonis 中分离的新木脂素，以及 25在体外测试了其合成类似物或具有醚键的相关物质及其相应的 C-8 硫和氮类似物对多诺瓦利什曼原虫无鞭毛体和前鞭毛体的活性。有些在 30 microM 时对 L. donovani 前鞭毛体有活性，但对细胞内无鞭毛体无活性。来自 V.pavonis 的天然新木脂素对 100 microM 的前鞭毛体有活性。在具有硫桥的那些化合物中发现了最高的选择性活性。β-酮硫化物 (3,4-二甲氧基)-8-(4'-甲基噻吩氧基)-苯丙酮对 L. 产生了 42% 的抑制作用。

  DOI：

  10.1016/s0031-9422(00)00240-5

文献信息

• Anti-leishmanial activity of neolignans from Virola species and synthetic analogues
  作者：Lauro E.S Barata、Lourivaldo S Santos、Pedro H Ferri、J.David Phillipson、Angela Paine、Simon L Croft

  DOI：10.1016/s0031-9422(00)00240-5

  日期：2000.11

  Surinamensin, a neolignan isolated from Virola surinamensis, 3,4,5-trimethoxy-8-[2',6'-dimethoxy-4'-(E)-propenylphenoxy]-phenylpropane, a neolignan isolated from Virola pavonis, and 25 of its synthetic analogues or correlated substances with ether linkages and their corresponding C-8 sulphur and nitrogen analogues, were tested for activity against Leishmania donovani amastigotes and promastigotes in

  Surinamensin，一种从 Virola surinamensis 中分离的新木脂素，3,4,5-trimethoxy-8-[2',6'-dimethoxy-4'-(E)-propenylphenoxy]-phenylpropane，一种从 Virola pavonis 中分离的新木脂素，以及 25在体外测试了其合成类似物或具有醚键的相关物质及其相应的 C-8 硫和氮类似物对多诺瓦利什曼原虫无鞭毛体和前鞭毛体的活性。有些在 30 microM 时对 L. donovani 前鞭毛体有活性，但对细胞内无鞭毛体无活性。来自 V.pavonis 的天然新木脂素对 100 microM 的前鞭毛体有活性。在具有硫桥的那些化合物中发现了最高的选择性活性。β-酮硫化物 (3,4-二甲氧基)-8-(4'-甲基噻吩氧基)-苯丙酮对 L. 产生了 42% 的抑制作用。
• DBU-Catalyzed Aerobic CDC Reaction of Thiophenols
  作者：Xuemin Jia、Xiao Ma、Wei Feng、Ji-Quan Zhang、Yonglong Zhao、Bing Guo、Lei Tang、Yuan-Yong Yang

  DOI：10.1021/acs.joc.2c02207

  日期：2022.12.16

  A convenient method was developed for the preparation of thiolated compounds via a DBU-catalyzed aerobic cross-dehydrogenative coupling (CDC) reaction. The established protocol is environmentally friendly and operationally simple. Substrates like (hetero)aryl acetates, (hetero)aryl ketones, and indoles could be transformed into the corresponding thiolated products in moderate to high yields and further

  通过DBU 催化的有氧交叉脱氢偶联 (CDC) 反应，开发了一种制备硫醇化化合物的简便方法。已建立的协议对环境友好且操作简单。(杂)芳基乙酸酯、(杂)芳基酮和吲哚等底物可以中高产率转化为相应的硫醇化产物，并以无预功能化的方式进一步应用于生物活性化合物的制备。
• Lapkin,I.I. et al., Journal of Organic Chemistry USSR (English Translation), 1976, vol. 12, p. 975 - 977
  作者：Lapkin,I.I. et al.

  DOI：——

  日期：——
• 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.
• Polyfluorination Using IF₅
  作者：Tadahito Fukuhara、Shoji Hara

  DOI：10.1021/jo101672g

  日期：2010.11.5

  The polyfluorination of alpha-(arylthio)carbonyl compounds was achieved by a successive application of polyfluorination using IF5, Friedel Crafts arylation, and desulfurizing fluorination using IF5. Three to six fluorine atoms were selectively introduced to the carbons located between the aromatic ring and the carbonyl group.