4-(methylsulfonyl)benzoylmethyl phenylacetate | 201737-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(methylsulfonyl)benzoylmethyl phenylacetate
• 英文别名: 2-[4-(Methanesulfonyl)phenyl]-2-oxoethyl phenylacetate；[2-(4-methylsulfonylphenyl)-2-oxoethyl] 2-phenylacetate
• CAS: 201737-94-2
• 化学式: C₁₇H₁₆O₅S
• 分子量: 332.377
• InChiKey: FFGBLORBEKAYGC-UHFFFAOYSA-N

物化性质

• 沸点：
  542.8±50.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(methylsulfonyl)benzoylmethyl phenylacetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 生成 罗非昔布
  参考文献：
  名称：

  3,4-二芳基取代2(5H)-呋喃酮的一锅法合成及其商业应用

  摘要：

  摘要 建立了3,4-二芳基取代的2(5H)-呋喃酮的一锅法合成方法，并通过完成罗非昔布的全合成，在温和的反应条件下，以良好的收率和纯度证明了其商业应用。图形概要

  DOI：

  10.1080/00397911.2011.577923
• 作为产物：
  描述：

  4-甲硫基苯乙酮 在 硫酸 、 氢溴酸 、 双氧水 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.58h， 生成 4-(methylsulfonyl)benzoylmethyl phenylacetate
  参考文献：
  名称：

  Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones

  摘要：

  Series of 5-substituted-3,4-diphenylfuran-2-ones were stereoselectively prepared. Their potential anti-proliferative effects on prostate cancer and some of their cyclooxygenases (COXs) inhibitory activities were evaluated. Structure activity relationship (SAR) data, acquired by substituent modification at the para-position and ortho-position of the C-3 phenyl ring and 5-substituted modification of the central furanone, showed that 3-(2-chloro-phenyl)-4-(4-methanesulfonyl-phenyl)-5-(1-methoxy-ethyl)-5H-furan-2-one (13p) was the most potent compound and could effectively reduce the proliferation of prostate cancer cells (PC3 cell IC50 = 20 mu M; PD PCDNA cell IC50 = 5 mu M; PD SKP2 cell IC50 = 5 mu M; DU145 cell IC50 = 25 mu M). The cell cycle analysis for 13p in DU145 indicated that 13p may induce G1 phase arrest. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.062

文献信息

• Synthesis of 3,4-Diarylsubstituted Maleic Anhydride/Maleimide via Unusual Oxidative Cyclization of Phenacyl Ester/Amide
  作者：Vijaya Raghavan Pattabiraman、Srinivas Padakanti、Venugopal Rao Veeramaneni、Manojit Pal、Koteswar Rao Yeleswarapu

  DOI：10.1055/s-2002-31901

  日期：——

  A simple and general method has been developed for the synthesis of 3,4-diarylsubstituted maleic anhydride and maleimide through tandem cyclization and oxidation reaction of phenacyl ester or amide. A wide variety of phenacyl esters or amides was treated with DBU under oxygen atmosphere to give the expected compounds in good to excellent yield. Mechanism of the reaction and application of the methodology

  开发了一种简单通用的方法，通过苯甲酰酯或酰胺的串联环化和氧化反应合成3,4-二芳基取代的马来酸酐和马来酰亚胺。多种苯甲酰酯或酰胺在氧气气氛下用 DBU 处理，得到预期的化合物，收率良好至极好。讨论了反应机理和方法学的应用。
• PROCESS OF PREPARING PHENYL HETEROCYCLES USEFUL AS COX-2 INHIBITORS
  申请人：MERCK & CO., INC.

  公开号：EP0912537B1

  公开（公告）日：2004-05-12
• Sulfonamido, azidosulfonyl and N-acetylsulfonamido analogues of rofecoxib: 4-[4-(N-acetylsulfonamido)phenyl]-3-(4-methanesulfonylphenyl)-2(5H)furanone is a potent and selective cyclooxygenase-2 inhibitor
  作者：Afshin Zarghi、P.N Praveen Rao、Edward E Knaus

  DOI：10.1016/j.bmcl.2004.01.076

  日期：2004.4

  4-[4-(N-Acetylsulfonamido)phenyl]-3-(4-methanesulfonylphenyl)-2(5H)furanone, possessing a N-acetylsulfonamido pharmacophore, has been identified as a potent and selective COX-2 inhibitor that has the potential to acetylate the COX-2 isozyme. (C) 2004 Elsevier Ltd. All rights reserved.
• WO9800416A1
  申请人：——

  公开号：——

  公开（公告）日：——
• US5840924A
  申请人：——

  公开号：US5840924A

  公开（公告）日：1998-11-24