3-(4-(methylthio)phenyl)-1-ptolylprop-2-en-1-one | 925457-28-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(4-(methylthio)phenyl)-1-ptolylprop-2-en-1-one
• 英文别名: 1-(4-Methylphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one
• CAS: 925457-28-9
• 化学式: C₁₇H₁₆OS
• 分子量: 268.379
• InChiKey: OZJHMGGPZMUIJN-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C(Solv: ethanol (64-17-5))
• 沸点：
  439.7±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-(4-(methylthio)phenyl)-1-ptolylprop-2-en-1-one 在 乙酸酐 、 四氯化锡 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 8.17h， 生成 2-(hydroxymethylene)-6-methyl-4-(4-(methylthio)phenyl)-1,2,3,4-tetrahydronaphthalen-1(2H)-one
  参考文献：
  名称：

  鬼臼毒素新型吡唑类似物的合成及药理研究

  摘要：

  鬼臼毒素的吡唑类似物是通过查耳酮途径合成的。这条路线因其操作条件简单和化学品容易获得而受到关注。最初，苯亚甲基苯乙酮（查耳酮）是通过苯乙酮与 4-（甲硫基）苯甲醛的 Claisen-Schmidt 反应以高产率制备的。通过查耳酮与碘化三甲基亚砜的反应，以良好的收率制备了环丙基酮。在无水存在下，通过环丙基酮的 Friedel-Craft 分子内环化反应以良好的收率制备四氢酮。氯化锡和醋酸酐。甲酰化的四氢萘酮得到取代的羟基亚甲基四氢萘酮。取代的羟基亚甲基四氢萘酮与水合肼缩合得到目标化合物。合成化合物的结构经IR、1H NMR和质谱技术证实。筛选标题化合物的抗有丝分裂和抗微生物活性。在合成的化合物环丙基酮和鬼臼毒素的吡唑类似物中，化合物7-(甲硫基)-5-(4-(甲硫基)苯基)-4,5-二氢-2H-苯并[g]吲唑比5-( 4-(甲硫基)苯基)-4,5-二氢-2H-苯并[g]吲唑、7-甲基-5-(4-(甲硫基)苯基)-4

  DOI：

  10.1134/s106816201404013x
• 作为产物：
  描述：

  对甲基苯乙酮 、 4-(甲基巯基)苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以79.25%的产率得到3-(4-(methylthio)phenyl)-1-ptolylprop-2-en-1-one
  参考文献：
  名称：

  鬼臼毒素新型吡唑类似物的合成及药理研究

  摘要：

  鬼臼毒素的吡唑类似物是通过查耳酮途径合成的。这条路线因其操作条件简单和化学品容易获得而受到关注。最初，苯亚甲基苯乙酮（查耳酮）是通过苯乙酮与 4-（甲硫基）苯甲醛的 Claisen-Schmidt 反应以高产率制备的。通过查耳酮与碘化三甲基亚砜的反应，以良好的收率制备了环丙基酮。在无水存在下，通过环丙基酮的 Friedel-Craft 分子内环化反应以良好的收率制备四氢酮。氯化锡和醋酸酐。甲酰化的四氢萘酮得到取代的羟基亚甲基四氢萘酮。取代的羟基亚甲基四氢萘酮与水合肼缩合得到目标化合物。合成化合物的结构经IR、1H NMR和质谱技术证实。筛选标题化合物的抗有丝分裂和抗微生物活性。在合成的化合物环丙基酮和鬼臼毒素的吡唑类似物中，化合物7-(甲硫基)-5-(4-(甲硫基)苯基)-4,5-二氢-2H-苯并[g]吲唑比5-( 4-(甲硫基)苯基)-4,5-二氢-2H-苯并[g]吲唑、7-甲基-5-(4-(甲硫基)苯基)-4

  DOI：

  10.1134/s106816201404013x

文献信息

• Novel 1,3,5-triphenyl-2-pyrazolines as anti-infective agents
  作者：P.M. Sivakumar、S. Prabhu Seenivasan、Vanaja Kumar、Mukesh Doble

  DOI：10.1016/j.bmcl.2010.03.083

  日期：2010.5

  Sixteen 1,3,5-triphenyl-2-pyrazolines were synthesized and their anti-infective activities (against Mycobacterium tuberculosis H(37)Rv, six bacterial and four fungal strains) were tested. Only compound with SO(2)CH(3) in the para position of the A-ring was active against the tubercular strain at 100 mu g/ml concentration. All compounds showed good anti infective activity against Escherichia coli and poor activity against Staphylococcus aureus. Compounds 4, 12, 13 and 14 exhibited reasonable activity against all the organisms tested (<0.309 mu M except against S. aureus. The activity of these compounds correlated with their lipophilic/hydrophilic nature. Compounds 4, 10 and 16 showed very good activity (>88% reduction) against four fungi studied at 2 mg/ml. All these compounds possess halogen substitutions. Compound 11 showed very high activity (>90%) against three fungi. Majority of the compounds showed more than 90% inhibition against one or two fungi. Since pyrazolines are reported to inhibit the activity of p-glycoprotein, they may prevent drug resistance developed by microorganism. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, antioxidant evaluation, and quantitative structure–activity relationship studies of chalcones
  作者：P. M. Sivakumar、P. K. Prabhakar、M. Doble

  DOI：10.1007/s00044-010-9342-1

  日期：2011.5

  Synthesis, antioxidant activity, and quantitative structure-activity relationship (QSAR) of 25 of chalcone derivatives is reported here. They were synthesized by Claisen-Schmidt reaction and were characterized by FTIR, NMR, and mass spectroscopy. Antioxidant activity is evaluated through four different methods namely, superoxide radical-scavenging, hydrogen peroxide scavenging, reducing power, and DPPH radical-scavenging assays. Generally, compounds with -SCH3 and -OCH3 in the para position of the A-ring and -OH in the B-ring were more active than others. In few cases some of the compounds were more active than ascorbic acid or butylated hydroxytoluene. QSAR was developed correlating the antioxidant activity with the structural features of the compounds and the predictive capability of the models was estimated using internal and external validation methods. All the predictions were within the 99% confidence level. Spatial, structural, and lipophilic properties of the compounds determine their antioxidant properties.