methyl (1R,2R,3S,5S)-3-(pentafluorobenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | 1422032-22-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: methyl (1R,2R,3S,5S)-3-(pentafluorobenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• CAS: 1422032-22-1
• 化学式: C₁₇H₁₆F₅NO₄
• 分子量: 393.31
• InChiKey: AEWXJXKLQDMACF-UYXSQOIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (1R,2R,3S,5S)-3-(pentafluorobenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 在 甲酸 、 potassium carbonate 、 锌 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 methyl (1R,2R,3S,5S)-3-(pentafluorobenzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate
  参考文献：
  名称：

  Modulating Cocaine Vaccine Potency through Hapten Fluorination

  摘要：

  Cocaine addiction is a long-lasting relapsing illness characterized by cycles of abuse, abstinence, and reinstatement, and antibody-based therapies could be a powerful therapeutic approach. Herein, we explored the possibility of using halogenated cocaine haptens to enhance the immunological properties of anti-cocaine vaccines. Three fluorine-containing cocaine haptens (GNF, GNCF and GN5F) and one chlorine-containing cocaine hapten (GNCl) were designed and synthesized, based upon the chemical scaffold of the only hapten that has reached clinical trials, succinyl norcocaine (SNC). Hapten GNF was found to retain potent cocaine affinity, and also elicit antibodies in a higher concentration than the parent structure SNC. Our data suggests that not only could strategic hapten fluorination be useful for improving upon the current cocaine vaccine undergoing clinical trials, but it may also be a valuable new approach, with application to any of the vaccines being developed for the treatment of drugs of abuse.

  DOI：

  10.1021/ja400356g
• 作为产物：
  描述：

  五氟苯甲酰氯 、 芽子碱甲酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以85%的产率得到methyl (1R,2R,3S,5S)-3-(pentafluorobenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
  参考文献：
  名称：

  Modulating Cocaine Vaccine Potency through Hapten Fluorination

  摘要：

  Cocaine addiction is a long-lasting relapsing illness characterized by cycles of abuse, abstinence, and reinstatement, and antibody-based therapies could be a powerful therapeutic approach. Herein, we explored the possibility of using halogenated cocaine haptens to enhance the immunological properties of anti-cocaine vaccines. Three fluorine-containing cocaine haptens (GNF, GNCF and GN5F) and one chlorine-containing cocaine hapten (GNCl) were designed and synthesized, based upon the chemical scaffold of the only hapten that has reached clinical trials, succinyl norcocaine (SNC). Hapten GNF was found to retain potent cocaine affinity, and also elicit antibodies in a higher concentration than the parent structure SNC. Our data suggests that not only could strategic hapten fluorination be useful for improving upon the current cocaine vaccine undergoing clinical trials, but it may also be a valuable new approach, with application to any of the vaccines being developed for the treatment of drugs of abuse.

  DOI：

  10.1021/ja400356g