2-cyclohexyl-1-(4-methylsulfanylphenyl)ethanone | 708276-22-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-cyclohexyl-1-(4-methylsulfanylphenyl)ethanone
• 英文别名: 2-cyclohexyl-1-(4-(methylthio)phenyl)ethan-1-one
• CAS: 708276-22-6
• 化学式: C₁₅H₂₀OS
• 分子量: 248.389
• InChiKey: MMIYHJIHRPXYTM-UHFFFAOYSA-N

物化性质

• 沸点：
  388.8±25.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  2-cyclohexyl-1-(4-methylsulfanylphenyl)ethanone 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以95%的产率得到2-cyclohexyl-1-(4-methanesulfonylphenyl)ethanone
  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：

  茴香硫醚 、 环己基乙酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以94%的产率得到2-cyclohexyl-1-(4-methylsulfanylphenyl)ethanone
  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

文献信息

• Divergent Synthesis of Alcohols and Ketones via Cross‐Coupling of Secondary Alcohols under Manganese Catalysis
  作者：Feixiang Sun、Jiamin Huang、Zhihong Wei、Conghui Tang、Weiping Liu

  DOI：10.1002/anie.202303433

  日期：2023.6.26

  A manganese-catalyzed cross-coupling of two secondary alcohols in a divergent synthesis of either γ-disubstituted alcohols or β-disubstituted ketones is herein reported. A wide range of different alcohols could undergo the cross-coupling process smoothly and furnish the corresponding products by using the same catalyst, with overall moderate to good yields.

  本文报道了在 γ-二取代醇或 β-二取代酮的不同合成中锰催化的两种仲醇的交叉偶联。多种不同的醇可以顺利地进行交叉偶联过程，并通过使用相同的催化剂提供相应的产品，总体收率中等至良好。
• Synthesis and Biological Evaluation of 2-Phenylpyran-4-ones:  A New Class of Orally Active Cyclooxygenase-2 Inhibitors
  作者：Francisco Caturla、Juan-Miguel Jiménez、Núria Godessart、Mercè Amat、Alvaro Cárdenas、Lídia Soca、Jordi Beleta、Hamish Ryder、María I. Crespo

  DOI：10.1021/jm049882t

  日期：2004.7.1

  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.