3β-(4-chlorophenyl)-2β-ethynyltropane | 1036404-10-0

• 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: 3β-(4-chlorophenyl)-2β-ethynyltropane
• 英文别名: 3beta-(4-Chlorophenyl)-2beta-ethynyltropane hydrochloride；(1R,2R,3S,5S)-3-(4-chlorophenyl)-2-ethynyl-8-methyl-8-azabicyclo[3.2.1]octane
• CAS: 1036404-10-0
• 化学式: C₁₆H₁₈ClN
• 分子量: 259.779
• InChiKey: KCUIYEZRUPAOPN-CAOSSQGBSA-N

物化性质

• 熔点：
  123-125 °C
• 沸点：
  341.9±42.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-硝基碘苯 、 3β-(4-chlorophenyl)-2β-ethynyltropane 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 以96%的产率得到3β-(4-chlorophenyl)-2β-(4-nitrophenylethynyl)tropane
  参考文献：
  名称：

  Synthesis and receptor binding properties of 2β-alkynyl and 2β-(1,2,3-triazol)substituted 3β-(substituted phenyl)tropane derivatives

  摘要：

  A series of 2b-alkynyl and 2b-(1,2,3-triazol) substituted 3b-(substituted phenyl) tropanes were synthesized and evaluated for affinities at dopamine, serotonin, and norepinephrine membrane transporters using competitive radioligand binding assays. All tested compounds were found to exhibit nanomolar or subnanomolar affinity for the dopamine transporter (DAT). One of the most potent and selective compounds in the series was 3b-(4-chlorophenyl)-2b-(4-nitrophenylethynyl) tropane (10c) that possessed an IC50 value of 0.9 nM at the DAT and K-i values of 230 nM and 620 nM at the norepinephrine transporter ( NET) and serotonin transporter (5-HTT), respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.008
• 作为产物：
  描述：

  3β-(4-chlorophenyl)-2β-(2,2-dibromovinyl)tropane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到3β-(4-chlorophenyl)-2β-ethynyltropane
  参考文献：
  名称：

  Synthesis and receptor binding properties of 2β-alkynyl and 2β-(1,2,3-triazol)substituted 3β-(substituted phenyl)tropane derivatives

  摘要：

  A series of 2b-alkynyl and 2b-(1,2,3-triazol) substituted 3b-(substituted phenyl) tropanes were synthesized and evaluated for affinities at dopamine, serotonin, and norepinephrine membrane transporters using competitive radioligand binding assays. All tested compounds were found to exhibit nanomolar or subnanomolar affinity for the dopamine transporter (DAT). One of the most potent and selective compounds in the series was 3b-(4-chlorophenyl)-2b-(4-nitrophenylethynyl) tropane (10c) that possessed an IC50 value of 0.9 nM at the DAT and K-i values of 230 nM and 620 nM at the norepinephrine transporter ( NET) and serotonin transporter (5-HTT), respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.008