dimethyl-2-(2'-(3',5'-difluorophenyl)acetyl)-2-(2'-(4'-(methylsulfonyl)phenyl)-2'-oxoethyl)propane-1,3-dioate | 228718-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl-2-(2'-(3',5'-difluorophenyl)acetyl)-2-(2'-(4'-(methylsulfonyl)phenyl)-2'-oxoethyl)propane-1,3-dioate
• 英文别名: Dimethyl 2-[2-(3,5-difluorophenyl)acetyl]-2-[2-(4-methylsulfonylphenyl)-2-oxoethyl]propanedioate
• CAS: 228718-03-4
• 化学式: C₂₂H₂₀F₂O₈S
• 分子量: 482.459
• InChiKey: HMEZXGNLKHWOTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  dimethyl-2-(2'-(3',5'-difluorophenyl)acetyl)-2-(2'-(4'-(methylsulfonyl)phenyl)-2'-oxoethyl)propane-1,3-dioate 在 硫酸 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 12.0h， 生成 2-(3,5-二氟苯基)-3-(4-(甲基磺酰基)苯基)-2-环戊烯-1-酮
  参考文献：
  名称：

  Efficient syntheses of 2-(3′,5′-difluorophenyl)-3-(4′-methylsulfonylphenyl)cyclopent-2-enone, a potent COX-2 inhibitor

  摘要：

  2-(3',5'-Difluorophenyl)-3-(4'-methylsulfonylphenyl)cyclopent-2-enone (1) displays high selectivity and potency against COX-2. Three efficient syntheses of this diarylcyclopentenone are described. The first approach employs a Suzuki coupling reaction as the key step while the second synthesis features an intramolecular Friedel-Crafts acylation. The third, and preferred route to this compound involves a sequential malonate alkylation and acylation and ring-closure sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00274-4
• 作为产物：
  描述：

  3,5-二氟苯乙酸 在 吡啶 、 草酰氯 、 magnesium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 dimethyl-2-(2'-(3',5'-difluorophenyl)acetyl)-2-(2'-(4'-(methylsulfonyl)phenyl)-2'-oxoethyl)propane-1,3-dioate
  参考文献：
  名称：

  Efficient syntheses of 2-(3′,5′-difluorophenyl)-3-(4′-methylsulfonylphenyl)cyclopent-2-enone, a potent COX-2 inhibitor

  摘要：

  2-(3',5'-Difluorophenyl)-3-(4'-methylsulfonylphenyl)cyclopent-2-enone (1) displays high selectivity and potency against COX-2. Three efficient syntheses of this diarylcyclopentenone are described. The first approach employs a Suzuki coupling reaction as the key step while the second synthesis features an intramolecular Friedel-Crafts acylation. The third, and preferred route to this compound involves a sequential malonate alkylation and acylation and ring-closure sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00274-4

文献信息

• Efficient syntheses of 2-(3′,5′-difluorophenyl)-3-(4′-methylsulfonylphenyl)cyclopent-2-enone, a potent COX-2 inhibitor
  作者：Dalian Zhao、Feng Xu、Cheng-yi Chen、Rich D. Tillyer、Edward J.J. Grabowski、Paul J. Reider、Cameron Black、Nathalie Ouimet、Peppi Prasit

  DOI：10.1016/s0040-4020(99)00274-4

  日期：1999.5

  2-(3',5'-Difluorophenyl)-3-(4'-methylsulfonylphenyl)cyclopent-2-enone (1) displays high selectivity and potency against COX-2. Three efficient syntheses of this diarylcyclopentenone are described. The first approach employs a Suzuki coupling reaction as the key step while the second synthesis features an intramolecular Friedel-Crafts acylation. The third, and preferred route to this compound involves a sequential malonate alkylation and acylation and ring-closure sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.