Methoxy-acetic acid 2-(4-methanesulfonyl-phenyl)-1,1-dimethyl-2-oxo-ethyl ester | 246869-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methoxy-acetic acid 2-(4-methanesulfonyl-phenyl)-1,1-dimethyl-2-oxo-ethyl ester
• 英文别名: [2-Methyl-1-(4-methylsulfonylphenyl)-1-oxopropan-2-yl] 2-methoxyacetate；[2-methyl-1-(4-methylsulfonylphenyl)-1-oxopropan-2-yl] 2-methoxyacetate
• CAS: 246869-13-6
• 化学式: C₁₄H₁₈O₆S
• 分子量: 314.359
• InChiKey: CARZUWODFNFGDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methoxy-acetic acid 2-(4-methanesulfonyl-phenyl)-1,1-dimethyl-2-oxo-ethyl ester 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 4-(4-Methanesulfonyl-phenyl)-3-methoxy-5,5-dimethyl-5H-furan-2-one
  参考文献：
  名称：

  SAR in the alkoxy lactone series: the discovery of DFP, a potent and orally active COX-2 inhibitor

  摘要：

  Extensive SAR has been established in the alkoxy lactone series and this has lead to the discovery of DFP (5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2-(5H)-furanone), a potent COX-2 inhibitor exhibiting in vivo efficacy in all models studied. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00365-0
• 作为产物：
  描述：

  p-(甲硫基)异丁酰苯 在 4-二甲氨基吡啶 、 Oxone 、 sodium hydroxide 、 甲基三辛基氯化铵 作用下， 以 四氯化碳 、 二氯甲烷 、 甲苯 为溶剂， 生成 Methoxy-acetic acid 2-(4-methanesulfonyl-phenyl)-1,1-dimethyl-2-oxo-ethyl ester
  参考文献：
  名称：

  SAR in the alkoxy lactone series: the discovery of DFP, a potent and orally active COX-2 inhibitor

  摘要：

  Extensive SAR has been established in the alkoxy lactone series and this has lead to the discovery of DFP (5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2-(5H)-furanone), a potent COX-2 inhibitor exhibiting in vivo efficacy in all models studied. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00365-0

文献信息

• [EN] SYNTHESIS METHODS OF FIROCOXIB AND INTERMEDIATE THEREOF<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE FIROCOXIB ET INTERMÉDIAIRE DE CELUI-CI
  申请人：SICHUAN QINGMU PHARMACEUTICAL CO LTD

  公开号：WO2019062561A1

  公开（公告）日：2019-04-04

  Provided herein the synthesis methods of firocoxib and an intermediate thereof. The synthesis of the first intermediate is performed through methylation of p-bromopropiophenone or through Friedel-Crafts acylation of bromobenzene, avoiding the use of environmental unfriendly thioethers as starting materials. The second intermediate is directly obtained by sulfonation of the first intermediate, wherein the sulfidation reaction and the oxidization reaction are shortened to one-step reaction. The sulfonation step greatly simplifies the reaction steps, shortens the reaction time, and improves the reaction efficiency. Meanwhile, an N-bromosuccinimide(NBS) catalyst system is also adopted in the hydroxylation of the second intermediate to directly obtain the firocoxib intermediate. Such an environmental friendly method is suitable for large-scale production, and the reaction rate is increased. In addition, the firocoxib synthesis method comprises the synthesis method of the firocoxib intermediate and can prepare firocoxib in a milder and more environmentally friendly manner.
• SAR in the alkoxy lactone series: the discovery of DFP, a potent and orally active COX-2 inhibitor
  作者：Y. Leblanc、P. Roy、S. Boyce、C. Brideau、C.C. Chan、S. Charleson、R. Gordon、E. Grimm、J. Guay、S. Léger、C.S. Li、D. Riendeau、D. Visco、Z. Wang、J. Webb、L.J. Xu、P. Prasit

  DOI：10.1016/s0960-894x(99)00365-0

  日期：1999.8

  Extensive SAR has been established in the alkoxy lactone series and this has lead to the discovery of DFP (5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2-(5H)-furanone), a potent COX-2 inhibitor exhibiting in vivo efficacy in all models studied. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.