[4-[6,8-Dihydroxy-5,9-bis(2,2,2-trifluoroethoxy)-6,8-dihydropyrrolo[3,4-g]quinolin-7-yl]-3-methylphenyl]methanesulfonamide | 1185886-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: [4-[6,8-Dihydroxy-5,9-bis(2,2,2-trifluoroethoxy)-6,8-dihydropyrrolo[3,4-g]quinolin-7-yl]-3-methylphenyl]methanesulfonamide
• CAS: 1185886-67-2
• 化学式: C₂₃H₂₁F₆N₃O₆S
• 分子量: 581.493
• InChiKey: WZIDBULLNBRMBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  1-{4-[6,8-dioxo-5,9-bis(2,2,2-trifluoroethoxy)-6,8-dihydro-7H-pyrrolo[3,4-g]quinolin-7-yl]-3-methylphenyl}methanesulfonamide 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 氯苯 、 甲苯 为溶剂， 反应 1.75h， 生成 1-{4-[8-hydroxy-6-oxo-5,9-bis(2,2,2-trifluoroethoxy)-6,8-dihydro-7H-pyrrolo[3,4-g]quinolin-7-yl]-3-methylphenyl}methanesulfonamide 、 1-{4-[6-hydroxy-8-oxo-5,9-bis(2,2,2-trifluoroethoxy)-6,8-dihydro-7H-pyrrolo[3,4-g]quinolin-7-yl]-3-methylphenyl}methanesulfonamide 、 [4-[6,8-Dihydroxy-5,9-bis(2,2,2-trifluoroethoxy)-6,8-dihydropyrrolo[3,4-g]quinolin-7-yl]-3-methylphenyl]methanesulfonamide
  参考文献：
  名称：

  Remote Electronic Control in the Regioselective Reduction of Succinimides: A Practical, Scalable Synthesis of EP4 Antagonist MF-310

  摘要：

  A practical large-scale chromatography-free synthesis of EP4 antagonist MF-310, a potential new treatment for chronic inflammation, is presented. The synthetic route provided MF-310 as its sodium salt in 10 steps and 17% overall yield from commercially available pyridine dicarboxylate 7. The key features of this sequence include a unique regioselective reduction of succinimide 2 controlled by the electronic-properties of a remote pyridine ring, preparation of cyclopropane carboxylic acid 3 via a Corey-Chaykovsky cyclopropanation, and a short synthesis of sulfonamide 5.

  DOI：

  10.1021/jo901267x

文献信息

• Remote Electronic Control in the Regioselective Reduction of Succinimides: A Practical, Scalable Synthesis of EP4 Antagonist MF-310
  作者：Carmela Molinaro、Danny Gauvreau、Gregory Hughes、Stephen Lau、Sophie Lauzon、Rémy Angelaud、Paul D. O’Shea、Jacob Janey、Michael Palucki、Scott R. Hoerrner、Conrad E. Raab、Rick R. Sidler、Michel Belley、Yongxin Han

  DOI：10.1021/jo901267x

  日期：2009.9.4

  A practical large-scale chromatography-free synthesis of EP4 antagonist MF-310, a potential new treatment for chronic inflammation, is presented. The synthetic route provided MF-310 as its sodium salt in 10 steps and 17% overall yield from commercially available pyridine dicarboxylate 7. The key features of this sequence include a unique regioselective reduction of succinimide 2 controlled by the electronic-properties of a remote pyridine ring, preparation of cyclopropane carboxylic acid 3 via a Corey-Chaykovsky cyclopropanation, and a short synthesis of sulfonamide 5.