(1R)-2-carbomethoxy-3-(2,2-dimethylbenzo[1,3]dioxol-5-yl)trop-2-ene | 639858-21-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1R)-2-carbomethoxy-3-(2,2-dimethylbenzo[1,3]dioxol-5-yl)trop-2-ene
• 英文别名: methyl (1R,5S)-3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
• CAS: 639858-21-2
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: URLMJPDSYJJPIK-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-2-carbomethoxy-3-(2,2-dimethylbenzo[1,3]dioxol-5-yl)trop-2-ene 在 盐酸 、 samarium diiodide 作用下， 以 甲醇 为溶剂， 反应 2.17h， 生成 (1R)-2β-carbomethoxy-3α-(3,4-diacetoxyphenyl)tropane hydrochloride
  参考文献：
  名称：

  Synthesis and biological activity of 2-Carbomethoxy-3-catechol-8-azabicyclo[3.2.1]octanes

  摘要：

  Cocaine inhibits the dopamine transporter and the consequent elevation of dopamine is thought to contribute to the addictive properties of cocaine. Tropane analogues of cocaine, targeted to the dopamine transporter (DAT), are a significant focus of drug design for cocaine addiction medications. Herein, we report the function of the ortho hydroxy substituents in dopamine with respect to the azabicyclo[3.2.1]octane skeleton. The introduction of the o-dihydroxyl functionality led to reduced binding potency at monoamine transporters, rather than enhanced interaction with the DAT. It is therefore likely that the binding site for these compounds on the DAT is not the same as that for dopamine. Notwithstanding the moderate potency of the free catechols (> 100 nM), 7 manifested stimulant activity with a duration of effect that exceeded 4 h in a rat locomotor activity assay. Compound 10, a diacetoxy prodrug for 7, substituted fully for cocaine in a rat drug-discrimination paradigm and is now undergoing further investigation as a potential medication for cocaine abuse. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.014
• 作为产物：
  描述：

  5-溴-2,2-二甲基-1,3-苯并二噁茂 在 四(三苯基膦)钯 、 正丁基锂 、 硼酸三异丙酯 、 sodium carbonate 、 lithium chloride 作用下， 以 various solvent(s) 为溶剂， 反应 18.5h， 生成 (1R)-2-carbomethoxy-3-(2,2-dimethylbenzo[1,3]dioxol-5-yl)trop-2-ene
  参考文献：
  名称：

  Synthesis and biological activity of 2-Carbomethoxy-3-catechol-8-azabicyclo[3.2.1]octanes

  摘要：

  Cocaine inhibits the dopamine transporter and the consequent elevation of dopamine is thought to contribute to the addictive properties of cocaine. Tropane analogues of cocaine, targeted to the dopamine transporter (DAT), are a significant focus of drug design for cocaine addiction medications. Herein, we report the function of the ortho hydroxy substituents in dopamine with respect to the azabicyclo[3.2.1]octane skeleton. The introduction of the o-dihydroxyl functionality led to reduced binding potency at monoamine transporters, rather than enhanced interaction with the DAT. It is therefore likely that the binding site for these compounds on the DAT is not the same as that for dopamine. Notwithstanding the moderate potency of the free catechols (> 100 nM), 7 manifested stimulant activity with a duration of effect that exceeded 4 h in a rat locomotor activity assay. Compound 10, a diacetoxy prodrug for 7, substituted fully for cocaine in a rat drug-discrimination paradigm and is now undergoing further investigation as a potential medication for cocaine abuse. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.014