tert-butyl (1R,3r,5S)-3-(allylamino)-8-azabicyclo[3.2.1]octane-8-carboxylate | 1251429-86-3

• 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: tert-butyl (1R,3r,5S)-3-(allylamino)-8-azabicyclo[3.2.1]octane-8-carboxylate
• CAS: 1251429-86-3
• 化学式: C₁₅H₂₆N₂O₂
• 分子量: 266.384
• InChiKey: MJEHIIYLUUHQSB-CLLJXQQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,3r,5S)-3-(allylamino)-8-azabicyclo[3.2.1]octane-8-carboxylate 、 4-三氟甲基苄基异腈酸酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Studies on the structure–activity relationship of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists. Part 2: Discovery of highly potent anti-HIV agents

  摘要：

  Modification of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists revealed that introducing a fluoro group at the 3-position of the 3-phenyl group to reduce metabolism did not adversely affect the high potency against HIV infection, and that replacing the piperidine ring with a tropane ring could deliver the most potent anti-HIV agents. Stereochemistry of the substituted tropane ring is essential for maintaining the potent anti-HIV activity because only exo-isomers displayed subnanomolar whole cell activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.046
• 作为产物：
  描述：

  丙烯胺 、 N-叔丁氧羰基-去甲托品酮 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 tert-butyl (1R,3r,5S)-3-(allylamino)-8-azabicyclo[3.2.1]octane-8-carboxylate 、 tert-butyl (1R,3s,5S)-3-(allylamino)-8-azabicyclo[3.2.1]octane-8-carboxylate
  参考文献：
  名称：

  Studies on the structure–activity relationship of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists. Part 2: Discovery of highly potent anti-HIV agents

  摘要：

  Modification of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists revealed that introducing a fluoro group at the 3-position of the 3-phenyl group to reduce metabolism did not adversely affect the high potency against HIV infection, and that replacing the piperidine ring with a tropane ring could deliver the most potent anti-HIV agents. Stereochemistry of the substituted tropane ring is essential for maintaining the potent anti-HIV activity because only exo-isomers displayed subnanomolar whole cell activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.046