3-methyl-1-(4-methanesulfonylphenyl)butan-1-one | 708276-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-1-(4-methanesulfonylphenyl)butan-1-one
• 英文别名: 3-methyl-1-(4-(methylsulfonyl)phenyl)butan-1-one；3-Methyl-1-(4-methylsulfonylphenyl)butan-1-one
• CAS: 708276-30-6
• 化学式: C₁₂H₁₆O₃S
• 分子量: 240.323
• InChiKey: AQQMFHINMHYKJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 3-methyl-1-(4-methanesulfonylphenyl)butan-1-one 在 PPA 作用下， 反应 16.0h， 以5%的产率得到3-Isopropyl-2-(4-methanesulfonyl-phenyl)-6-methyl-pyran-4-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：

  异戊酰氯 在 三氯化铝 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 3-methyl-1-(4-methanesulfonylphenyl)butan-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

文献信息

• DABCO-promoted photocatalytic C–H functionalization of aldehydes
  作者：Bruno Maia da Silva Santos、Mariana dos Santos Dupim、Cauê Paula de Souza、Thiago Messias Cardozo、Fernanda Gadini Finelli

  DOI：10.3762/bjoc.17.205

  日期：——

  Herein we present a direct application of DABCO, an inexpensive and broadly accessible organic base, as a hydrogen atom transfer (HAT) abstractor in a photocatalytic strategy for aldehyde C–H activation. The acyl radicals generated in this step were arylated with aryl bromides through a well stablished nickel cross-coupling methodology, leading to a variety of interesting aryl ketones in good yields. We also performed computational calculations to shine light in the HAT step energetics and determined an optimized geometry for the transition state, showing that the hydrogen atom transfer between aldehydes and DABCO is a mildly endergonic, yet sufficiently fast step. The same calculations were performed with quinuclidine, for comparison of both catalysts and the differences are discussed.

  在这里，我们提出了一种直接应用DABCO的方法，DABCO是一种廉价且广泛可获得的有机碱，作为光催化策略中醛的C-H活化的氢原子转移（HAT）抽取剂。在这一步骤中生成的酰基自由基通过一种成熟的镍交叉偶联方法与芳基溴化物芳基化，产生各种有趣的芳基酮，收率良好。我们还进行了计算计算，以阐明HAT步骤的能量学，并确定了过渡态的优化几何构型，表明醛和DABCO之间的氢原子转移是一个轻微的能量吸收过程，但足够快速。为了比较两种催化剂，我们还对喹啉进行了相同的计算，并讨论了它们之间的差异。
• Bicycle pyrazole derivative
  申请人：Nakahira Hiroyuki

  公开号：US20070082908A1

  公开（公告）日：2007-04-12

  A compound represented by the following formula (I), a prodrug thereof, or a pharmaceutically acceptable salt of either. These are compounds having high DPP-IV inhibitory activity and improved in safety, nontoxicity, etc. (I) [In the formula, R 1 represents hydrogen, optionally substituted alkyl, etc.; the solid line and dotted line between A 1 and A 2 indicate a double bond (A 1 =A 2 ), etc.; A 1 represents a group represented by the formula C(R 2 ), etc.; A 2 represents a group represented by the formula C(R 4 ), etc.; R 2 represents hydrogen, optionally substituted alkyl, etc.; R 4 represents hydrogen, optionally substituted alkyl, etc.; R 6 represents hydrogen, optionally substituted aryl, etc.; and —Y represents, e.g.; a group represented by the formula (A): (A) (wherein m1 is 0, 1, 2, or 3; and R 7 is absent, or one or two R 7 's are present and each independently represents optionally substituted alkyl, etc.).]

  以下化合物的公式（I）或其前药，或者是任何一种药学上可接受的盐。这些化合物具有高DPP-IV抑制活性和改善安全、无毒性等特点。（I）[在公式中，R1代表氢，可选取代的烷基等；A1和A2之间的实线和虚线表示双键（A1=A2），等等；A1代表由公式C（R2）等表示的基团；A2代表由公式C（R4）等表示的基团；R2代表氢，可选取代的烷基等；R4代表氢，可选取代的烷基等；R6代表氢，可选取代的芳基等；而—Y代表例如由公式（A）表示的一个基团：（A）（其中m1为0、1、2或3；R7不存在，或者存在一个或两个R7，每个独立地代表可选取代的烷基等）。]
• 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.