1-[4-(甲硫基)苯基]-3-苯基-1-丙酮 | 40027-88-1

• 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
• 中文名称: 1-[4-(甲硫基)苯基]-3-苯基-1-丙酮
• 英文名称: 1-(4-(methylsulfanyl)phenyl)-3-phenylpropan-1-one
• 英文别名: 1-(4-(methylthio)phenyl)-3-phenylpropan-1-one；3-Phenyl-4'-thiomethylpropiophenone；1-(4-methylsulfanylphenyl)-3-phenylpropan-1-one
• CAS: 40027-88-1
• 化学式: C₁₆H₁₆OS
• mdl: MFCD03842925
• 分子量: 256.368
• InChiKey: AQGAYFGXRQFEGI-UHFFFAOYSA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  421.0±38.0 °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：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  1-[4-(甲硫基)苯基]-3-苯基-1-丙酮 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以85%的产率得到1-(4-(methylsulfonyl)phenyl)-3-phenylpropan-1-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-Phenylpyran-4-ones:  A New Class of Orally Active Cyclooxygenase-2 Inhibitors

  摘要：

  A series of 2-phenylpyran-4-ones were prepared and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2). Extensive structure-activity relationship work was carried out within this series, and a number of potent and selective COX-2 inhibitors were identified. Compounds having a p-methylsulfone group at the 2-phenyl ring showed the best COX-2 inhibitory activity. The introduction of a substituted phenoxy ring at position 3 enhanced both the in vitro and in vivo activity within the series. A selected group of 3-phenoxypyran-4-ones exhibited excellent activity in an experimental model of pyresis. The in vivo antiinflammatory activity of these compounds was confirmed with the evaluation of their antiarthritic and analgesic effectiveness. Moreover, their pharmacokinetic profile in rats is compatible with a once a day administration by oral route in humans. Within this novel series, compounds 21, 31, 34, and 35 have been selected for further preclinical. and clinical evaluation.

  DOI：

  10.1021/jm049882t
• 作为产物：
  描述：

  1-(4-methylthiophenyl)-3-phenylprop-2-en-1-one 在 iron(III) chloride 、 六氟异丙醇 作用下， 以 1,2-二氯乙烷 为溶剂， 以66 %的产率得到1-[4-(甲硫基)苯基]-3-苯基-1-丙酮
  参考文献：
  名称：

  铁催化聚甲基氢硅氧烷高效共轭还原 α,β-不饱和酮

  摘要：

  据报道，铁催化的 α,β-不饱和酮与 PMHS（聚甲基氢硅氧烷）的无配体共轭还原可产生相应的羰基化合物，产率高达 93%。这种操作简单的方案显示了广泛的底物范围，使用现成的 PMHS 作为具有成本效益且易于处理的还原剂。

  DOI：

  10.1039/d4ob00664j

文献信息

• Nitrosated and nitrosylated cyclooxygenase-2 inhibitors, compositions and methods of use
  申请人：——

  公开号：US20010041726A1

  公开（公告）日：2001-11-15

  The present invention describes novel nitrosated and/or nitrosylated cyclooxygenase 2 (COX-2) inhibitors and novel compositions comprising at least one nitrosated and/or nitrosylated cyclooxygenase 2 (COX-2) inhibitor, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or optionally, at least one therapeutic agent, such as, steroids, nonsteroidal antiinflammatory compounds (NSAID), 5-lipoxygenase (5-LO) inhibitors, leukotriene B 4 (LTB 4 ) receptor antagonists, leukotriene A 4 (LTA 4 ) hydrolase inhibitors, 5-HT agonists, 3-hydroxy-3-methylglutaryl coenzyme A (HMGCoA) inhibitors, H antagonists, antineoplastic agents, antiplatelet agents, decongestants, diuretics, sedating or non-sedating anti-histamines, inducible nitric oxide synthase inhibitors, opioids, analgesics, Helicobacter pylori inhibitors, proton pump inhibitors, isoprostane inhibitors, and mixtures thereof. The present invention also provides novel compositions comprising at least one parent COX-2 inhibitor and at least one nitric oxide donor, and, optionally, at least one therapeutic agent. The present invention also provides kits and methods for treating inflammation, pain and fever; for treating and/or improving the gastrointestinal properties of COX-2 inhibitors; for facilitating wound healing; for treating and/or preventing renal toxicity; and for treating and/or preventing other disorders resulting from elevated levels of cyclooxygenase-2.

  本发明描述了新颖的硝化和/或亚硝化环氧合酶2（COX-2）抑制剂以及包含至少一种硝化和/或亚硝化环氧合酶2（COX-2）抑制剂的新型组合物，以及可选地，至少一种捐赠、转移或释放一氧化氮、刺激内源性一氧化氮合成、提高内源性内皮源性舒张因子水平或是一氧化氮合酶底物的化合物，和/或可选地，至少一种治疗剂，如类固醇、非甾体抗炎化合物（NSAID）、5-脂氧合酶（5-LO）抑制剂、白三烯B4（LTB4）受体拮抗剂、白三烯A4（LTA4）水解酶抑制剂、5-HT激动剂、3-羟基-3-甲基戊二酰辅酶A（HMGCoA）抑制剂、H受体拮抗剂、抗肿瘤药物、抗血小板药物、解充血剂、利尿剂、镇静或非镇静抗组胺药、诱导型一氧化氮合酶抑制剂、阿片类药物、镇痛剂、幽门螺杆菌抑制剂、质子泵抑制剂、异前列腺素抑制剂以及其混合物。本发明还提供了包含至少一种母体COX-2抑制剂和至少一种一氧化氮供体的新型组合物，以及可选地，至少一种治疗剂。本发明还提供了用于治疗炎症、疼痛和发热的工具和方法；用于治疗和/或改善COX-2抑制剂的胃肠道特性；用于促进伤口愈合；用于治疗和/或预防肾毒性；以及用于治疗和/或预防由于环氧合酶-2水平升高而导致的其他疾病的工具和方法。
• In Water and under Mild Conditions: α‐Alkylation of Ketones with Alcohols by Phase‐Transfer‐Assisted Borrowing Hydrogen Catalysis
  作者：Lena Rakers、Felix Schäfers、Frank Glorius

  DOI：10.1002/chem.201804308

  日期：2018.10.17

  produces water as the only by‐product. Nevertheless, harsh conditions such as high temperatures and organic solvents are usually required. Herein, we present a strategy to perform the α‐alkylation of ketones in aqueous media at mild temperatures by combining borrowing hydrogen with phase‐transfer catalysis. A broad scope of methyl ketones was functionalized with alkyl and benzyl alcohols in moderate

  借用氢是一种有力且绿色的技术，可将现成的醇用作烷基化剂，并产生水作为唯一的副产物。然而，通常需要苛刻的条件，例如高温和有机溶剂。本文中，我们提出了一种策略，通过将借入氢与相转移催化相结合，在温和的温度下在水性介质中进行酮的α-烷基化反应。烷基和苯甲醇在40°C下以中等至良好的收率官能化了范围广泛的甲基酮。该协议在大规模和室温下也非常有效。
• Neutral-Eosin Y-Catalyzed Regioselective Hydroacylation of Aryl Alkenes under Visible-Light Irradiation
  作者：Xinxin Tang、Jie Wu、Haiwang Liu、Fei Xue、Mu Wang

  DOI：10.1055/a-1319-6237

  日期：2021.3

  The hydroacylation of styrene derivatives were achieved by employing neutral eosin Y as a direct hydrogen atom transfer (HAT) catalyst under visible-light irradiation. Exclusive anti-Markovnikov selectivity could be obtained. Aldehydes and styrenes with various substituents were tolerated (>20 examples) to achieve products with moderate to high yields. The key acyl radical intermediate was generated

  通过在可见光照射下使用中性曙红 Y 作为直接氢原子转移 (HAT) 催化剂来实现苯乙烯衍生物的加氢酰化。可以获得独特的抗马尔科夫尼科夫选择性。可以容忍具有各种取代基的醛和苯乙烯（> 20 个例子）以实现中等至高产率的产品。关键的酰基自由基中间体由光激发的曙红 Y 诱导的直接 HAT 过程产生。随后加入苯乙烯和反向 HAT 过程产生酮产物。
• Acceptorless dehydrogenation and dehydrogenative coupling of alcohols catalysed by protic NHC ruthenium complexes
  作者：Weihong Chang、Xue Gong、Shuizhong Wang、Ling-Ping Xiao、Guoyong Song

  DOI：10.1039/c7ob00542c

  日期：——

  A new family of protic NHC Ru complexes ligated with a phosphine-tethered imidazole moiety were prepared, which can act as excellent catalysts for acceptorless dehydrogenation of secondary alcohols and dehydrogenative coupling of primary and secondary alcohols, thus leading to the formation of a variety of carbonyl compounds with release of H2.

  制备了与膦系咪唑部分连接的新的质子NHC Ru复合物家族，可以作为仲醇无受体脱氢以及伯醇和仲醇脱氢偶联的极佳催化剂，从而导致形成多种羰基释放H 2的化合物。
• NITROSATED AND NITROSYLATED CYCLOOXYGENASE-2 INHIBITORS, COMPOSITIONS AND METHODS OF USE
  申请人：BANDARAGE Ramani R.

  公开号：US20090099139A1

  公开（公告）日：2009-04-16

  The present invention describes novel nitrosated and/or nitrosylated cyclooxygenase 2 (COX-2) inhibitors and novel compositions comprising at least one nitrosated and/or nitrosylated cyclooxygenase 2 (COX-2) inhibitor, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or optionally, at least one therapeutic agent. The present invention also provides novel compositions comprising at least one parent COX-2 inhibitor and at least one nitric oxide donor, and, optionally, at least one therapeutic agent. The present invention also provides kits and methods for treating inflammation, pain and fever; for treating and/or improving the gastrointestinal properties of COX-2 inhibitors; for facilitating wound healing; for treating and/or preventing renal toxicity; and for treating and/or preventing other disorders resulting from elevated levels of cyclooxygenase-2.

  本发明描述了新型的亚硝酸化和/或亚硝基化环氧合酶2（COX-2）抑制剂，以及包含至少一种亚硝酸化和/或亚硝基化环氧合酶2（COX-2）抑制剂的新型组合物，可选择地包含至少一种捐赠、转移或释放一氧化氮、刺激内源性合成一氧化氮、提高内源性内皮衍生松弛因子水平或是一氧化氮合酶底物的化合物，以及/或可选择地包含至少一种治疗剂。本发明还提供了包含至少一种母体COX-2抑制剂和至少一种一氧化氮供体的新型组合物，可选择地包含至少一种治疗剂。本发明还提供了用于治疗炎症、疼痛和发热的套件和方法；用于治疗和/或改善COX-2抑制剂的胃肠道特性；用于促进伤口愈合；用于治疗和/或预防肾毒性；以及用于治疗和/或预防由于升高的环氧合酶-2水平而引起的其他疾病的方法。