Methanesulfonic acid 4,4,4-trifluoro-1-(4-trifluoromethyl-phenyl)-butyl ester | 514843-77-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Methanesulfonic acid 4,4,4-trifluoro-1-(4-trifluoromethyl-phenyl)-butyl ester
• 英文别名: [4,4,4-Trifluoro-1-[4-(trifluoromethyl)phenyl]butyl] methanesulfonate
• CAS: 514843-77-7
• 化学式: C₁₂H₁₂F₆O₃S
• 分子量: 350.282
• InChiKey: FTXAAAXRWYYQLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid 4,4,4-trifluoro-1-(4-trifluoromethyl-phenyl)-butyl ester 在 titanium(IV) isopropylate 、 potassium carbonate 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 生成 (S)-2-Methyl-4-(4-methyl-piperidin-4-yl)-1-[(S)-4,4,4-trifluoro-1-(4-trifluoromethyl-phenyl)-butyl]-piperazine
  参考文献：
  名称：

  Piperazine-Based CCR5 Antagonists as HIV-1 Inhibitors. IV. Discovery of 1-[(4,6-Dimethyl-5-pyrimidinyl)carbonyl]- 4-[4-{2-methoxy-1(R)-4-(trifluoromethyl)phenyl}ethyl-3(S)-methyl-1-piperazinyl]- 4-methylpiperidine (Sch-417690/Sch-D), a Potent, Highly Selective, and Orally Bioavailable CCR5 Antagonist

  摘要：

  The nature and the size of the benzylic substituent are shown to be the key to controlling receptor selectivity (CCR5 vs M1, M2) and potency in the title compounds. Optimization of the lead benzylic methyl compound 3 led to the methoxymethyl analogue 30, which had excellent receptor selectivity and oral bioavailability in rats and monkeys. Compound 30 (Sch-417690/Sch-D), a potent inhibitor of HIV-1 entry into target cells, is currently in clinical trials.

  DOI：

  10.1021/jm0304515
• 作为产物：
  描述：

  对三氟甲基苯甲醛 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Methanesulfonic acid 4,4,4-trifluoro-1-(4-trifluoromethyl-phenyl)-butyl ester
  参考文献：
  名称：

  Piperazine-Based CCR5 Antagonists as HIV-1 Inhibitors. IV. Discovery of 1-[(4,6-Dimethyl-5-pyrimidinyl)carbonyl]- 4-[4-{2-methoxy-1(R)-4-(trifluoromethyl)phenyl}ethyl-3(S)-methyl-1-piperazinyl]- 4-methylpiperidine (Sch-417690/Sch-D), a Potent, Highly Selective, and Orally Bioavailable CCR5 Antagonist

  摘要：

  The nature and the size of the benzylic substituent are shown to be the key to controlling receptor selectivity (CCR5 vs M1, M2) and potency in the title compounds. Optimization of the lead benzylic methyl compound 3 led to the methoxymethyl analogue 30, which had excellent receptor selectivity and oral bioavailability in rats and monkeys. Compound 30 (Sch-417690/Sch-D), a potent inhibitor of HIV-1 entry into target cells, is currently in clinical trials.

  DOI：

  10.1021/jm0304515