8-ethoxycarbonyl-3β-(4-trifluoromethylphenyl)-3α-hydroxy-8-azabicyclo[3.2.1]octane | 1204302-62-4

• 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: 8-ethoxycarbonyl-3β-(4-trifluoromethylphenyl)-3α-hydroxy-8-azabicyclo[3.2.1]octane
• CAS: 1204302-62-4
• 化学式: C₁₇H₂₀F₃NO₃
• 分子量: 343.346
• InChiKey: LWZUXKDMRZDPPO-FOLVSLTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-ethoxycarbonyl-3β-(4-trifluoromethylphenyl)-3α-hydroxy-8-azabicyclo[3.2.1]octane 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到8-ethoxycarbonyl-3-(4-trifluorophenyl)-8-azabicyclo[3.2.1]oct-2-ene
  参考文献：
  名称：

  Synthesis and monoamine transporter affinity of 3α-arylmethoxy-3β-arylnortropanes

  摘要：

  A series of 3-arylnortrop-2-enes and 3 alpha-arylmethoxy-3 beta-arylnortropanes were synthesized and evaluated for binding affinity at monoamine transporters. The 3-(3,4-dichlorophenyl)nortrop-2-ene (6e) exhibited high affinity for the SERT (K-i = 0.3 nM). The 3 alpha-arylmethoxy-3 beta-arylnortropanes were generally SERT selective with the 3 alpha-(3,4-dichlorophenylmethoxy)-3 beta phenylnortrop-2-ene (7c) possessing subnanomolar potency (K-i = 0.061 nM). However, 3 alpha-(3,4-dichlorophenylmethoxy)-3 beta-phenylnortrop-2-ene (7b) exhibited high affinity at all three transporters [(DAT K-i = 22 nM), (SERT K-i = 6 nM) and (NET K-i = 101 nM)]. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.087
• 作为产物：
  描述：

  N-乙氧羰基-4-托品酮 、 对溴三氟甲苯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以50%的产率得到8-ethoxycarbonyl-3β-(4-trifluoromethylphenyl)-3α-hydroxy-8-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis and monoamine transporter affinity of 3α-arylmethoxy-3β-arylnortropanes

  摘要：

  A series of 3-arylnortrop-2-enes and 3 alpha-arylmethoxy-3 beta-arylnortropanes were synthesized and evaluated for binding affinity at monoamine transporters. The 3-(3,4-dichlorophenyl)nortrop-2-ene (6e) exhibited high affinity for the SERT (K-i = 0.3 nM). The 3 alpha-arylmethoxy-3 beta-arylnortropanes were generally SERT selective with the 3 alpha-(3,4-dichlorophenylmethoxy)-3 beta phenylnortrop-2-ene (7c) possessing subnanomolar potency (K-i = 0.061 nM). However, 3 alpha-(3,4-dichlorophenylmethoxy)-3 beta-phenylnortrop-2-ene (7b) exhibited high affinity at all three transporters [(DAT K-i = 22 nM), (SERT K-i = 6 nM) and (NET K-i = 101 nM)]. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.087