1-(4-methoxyphenyl)-3-(4-(methylthio)phenyl)prop-2-en-1-one | 121646-02-4

• 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: 1-(4-methoxyphenyl)-3-(4-(methylthio)phenyl)prop-2-en-1-one
• 英文别名: 1-(4-methoxyphenyl)-3-(4-methylmercaptophenyl)-2-en-1-one；2-Propen-1-one, 1-(4-methoxyphenyl)-3-[4-(methylthio)phenyl]-；1-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)prop-2-en-1-one
• CAS: 121646-02-4
• 化学式: C₁₇H₁₆O₂S
• 分子量: 284.379
• InChiKey: ZGIOCWWESCNBFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  461.9±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-3-(4-(methylthio)phenyl)prop-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-methoxy-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：

  4-(甲基巯基)苯甲醛 、 对甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以80.1%的产率得到1-(4-methoxyphenyl)-3-(4-(methylthio)phenyl)prop-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

• 酰基取代吡唑啉硫鎓盐衍生物的制备及其应用
  申请人：同济大学

  公开号：CN112574110B

  公开（公告）日：2022-04-19

  酰基取代吡唑啉硫鎓盐衍生物的制备及其应用，具体涉及下述式(I)所示的N‑1位酰基取代吡唑啉硫鎓盐衍生物的制备及其应用、光固化组合物以及式(I)所示的酰基取代吡唑啉硫鎓盐衍生物的制备方法。与普通的光引发剂相比，本发明的式(I)所示的酰基取代吡唑啉硫鎓盐衍生物光谱更加红移，与商品化LED光源更加匹配；同时，该类硫鎓盐作为光生酸剂不仅可以引发阳离子聚合反应，同时，分子自身及其降解产物还可以作为II型自由基光引发剂引发自由基的聚合；另外，该类硫鎓盐衍生物合成步骤比较简单，适用的配方体系多样，有望成为UV‑Vis‑LED可激发的光固化涂料或油墨工业化的生产和应用的光引发剂。
• Visible light catalyzed reaction of α-bromochalcones with chalcones: direct access to the urundeuvine scaffold
  作者：Bhupal Singh Karki、Mukund M. D. Pramanik、Ruchir Kant、Namrata Rastogi

  DOI：10.1039/c8ob01881b

  日期：——

  The α-keto vinyl radicals generated from α-bromochalcones under visible light photoredox catalyzed conditions were trapped by chalcones. The subsequent intramolecular cyclization of the resulting benzylic radicals led to the synthesis of dihydronaphthalenes, which were conveniently oxidized to the corresponding naphthalenes. The strategy was adopted successfully for synthesizing derivatives of urundeuvine

  在可见光光氧化还原催化条件下，α-溴查耳酮生成的α-酮乙烯基自由基被查耳酮捕获。所得苄基基团的随后分子内环化导致二氢萘的合成，其被方便地氧化成相应的萘。该策略已成功采用，用于合成尺und蛇形查尔酮的衍生物，否则只能从天然来源获得。
• 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.
• Synthesis, antimicrobial and antioxidant activities of 2-[1-{3,5-diaryl-4,5-dihydro-1H-pyrazolenyl}]-4-(4-nitrophenyl)-[1,3]-thiazoles
  作者：Prajwal Lourdes Lobo、Boja Poojary、Manjunatha Kumsi、Vinaya Chandra、Nalilu Sucheta Kumari、K. R. Chandrashekar

  DOI：10.1007/s00044-012-0154-3

  日期：2013.4

  In this study, various substituted chalcones, prepared by condensing substituted acetophenones with substituted aldehydes/arylfurfurals, were treated with thiosemicarbazide in basic media to produce 1-thiocarbonyl-3,5-disubstituted pyrazolines which on further reaction with substituted phenacyl bromides afforded the title compounds in good yield. Structures of the newly synthesized compounds were assigned on the basis of elemental analyses, IR, H-1 NMR, and mass spectral studies. The newly synthesized compounds were tested for their in vitro antibacterial and antifungal activities against a variety of microorganisms and antioxidant activities by diphenylpicrylhydrazyl radical scavenging assay. Among the derivatives, compounds 3b, 3e, 6a, and 6h were identified as potent antioxidants. Compounds 3d, 3e, and 6a-f have emerged as the most promising antimicrobial agents displaying the maximum activity against all the tested microorganisms.