tert-butyl-(3R,5S,6E)-7-[6,7,8-trifluoro-4-(4-fluorophenylthio)quinoline-3-yl]-3,5-dihydroxyhept-6-enoate | 1352429-10-7

• 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: tert-butyl-(3R,5S,6E)-7-[6,7,8-trifluoro-4-(4-fluorophenylthio)quinoline-3-yl]-3,5-dihydroxyhept-6-enoate
• CAS: 1352429-10-7
• 化学式: C₂₆H₂₅F₄NO₄S
• 分子量: 523.548
• InChiKey: KSSFPCUJERRFJJ-MWRSBEEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.65
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl-(3R,5S,6E)-7-[6,7,8-trifluoro-4-(4-fluorophenylthio)quinoline-3-yl]-3,5-dihydroxyhept-6-enoate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以244.1 g的产率得到(3R,5S,6E)-7-[4-(4-fluorophenylthio)-6,7,8-trifluoroquinolin-3-yl]-3,5-dihydroxy-6-heptenoic acid
  参考文献：
  名称：

  Development of a Practical and Efficient Synthesis of SIPI-4884, a HMG CoA Reductase Inhibitor for the Treatment of Hypercholesterolemia

  摘要：

  An improved process of the novel HMG CoA reductase inhibitor SIPI-4884 has been developed for early preclinical pharmacology and safety studies, and it was made up with an efficient nine-step and scalable process. Significant improvements in the nucleophilic substitution, reduction, Wittig-Horner reaction, and preparation of calcium salt were demonstrated. The overall yield was improved to 17.2%.

  DOI：

  10.1021/op400060z
• 作为产物：
  描述：

  4-(4-fluorophenylthio)-6,7,8-trifluoroquinoline-3-methanol 在 2,2,6,6-四甲基哌啶 、 盐酸 、 正丁基锂 、 水 、 三溴化磷 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 tert-butyl-(3R,5S,6E)-7-[6,7,8-trifluoro-4-(4-fluorophenylthio)quinoline-3-yl]-3,5-dihydroxyhept-6-enoate
  参考文献：
  名称：

  Development of a Practical and Efficient Synthesis of SIPI-4884, a HMG CoA Reductase Inhibitor for the Treatment of Hypercholesterolemia

  摘要：

  An improved process of the novel HMG CoA reductase inhibitor SIPI-4884 has been developed for early preclinical pharmacology and safety studies, and it was made up with an efficient nine-step and scalable process. Significant improvements in the nucleophilic substitution, reduction, Wittig-Horner reaction, and preparation of calcium salt were demonstrated. The overall yield was improved to 17.2%.

  DOI：

  10.1021/op400060z