methyl (1R)-8-methyl-8-azabicyclo<3.2.1>oct-2-ene-2-carboxylate | 43021-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (1R)-8-methyl-8-azabicyclo<3.2.1>oct-2-ene-2-carboxylate
• 英文别名: methyl (1R)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
• CAS: 43021-26-7；50373-10-9；91280-37-4；127379-24-2
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: MPSNEAHFGOEKBI-NHSZFOGYSA-N

物化性质

• 沸点：
  72-73 °C(Press: 0.45 Torr)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  T+
• 危险类别码：
  R26/27/28,R43
• 危险品运输编号：
  UN 1544 6.1/PG 2
• WGK Germany：
  3
• 海关编码：
  2933990090
• 安全说明：
  S22,S36/37/39,S45

反应信息

• 作为产物：
  描述：

  甲醇 、 methyl (1R)-8-methyl-8-azabicyclo<3.2.1>oct-2-ene-2-carboxylate hydrochloride 在 硫酸 作用下， 反应 24.0h， 以59%的产率得到methyl (1R)-8-methyl-8-azabicyclo<3.2.1>oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis of 3-arylecgonine analogs as inhibitors of cocaine binding and dopamine uptake

  摘要：

  3-Arylecgonine analogues were synthesized and characterized by 1H and 13C NMR, IR, and MS. The compounds were synthesized as racemates from cycloheptatriene-7-carboxylic acid or enantiomerically from (-)-cocaine. These analogues were tested for their ability to inhibit [3H]cocaine binding to bovine striatal tissue and to inhibit [3H]dopamine uptake into striatal synaptosomes. Methyl (1RS-2-exo-3-exo)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-ca rboxylate was the most potent analogue. IC50 values for inhibition of cocaine binding and dopamine uptake were 20 and 100 nM, respectively. The racemates and the 1R isomers were equally potent inhibitors of binding and uptake. Methyl (1RS-2-endo-3-exo)-3-(2,4-dinitrophenyl)-8-methyl-8-azabicyclo[3.2 .1]octane- 2-carboxylate was the least potent. IC50 for inhibition of both binding and uptake was 40 microM.

  DOI：

  10.1021/jm00169a036

文献信息

• PROCESS FOR THE PREPARATION OF RADIOIODINATED 3-FLUOROPROPYL-NOR-Beta-CIT
  申请人：MALLINCKRODT LLC

  公开号：US20150087838A1

  公开（公告）日：2015-03-26

  The invention generally provides processes for the preparation of radioiodinated 3-fluoropropyl-nor-β-CIT. In particular, the process uses an arylsilane intermediate, thus avoiding the use of hexamethylditin, and reducing the number of steps previously required for the preparation of radioiodinated 3-fluoropropyl-nor-β-CIT from anhydroecgonine methyl ester. The invention also relates to the alkylation of a nortropane to the corresponding N-(3-fluoropropyl) analogue using 3-fluoropropanal.

  该发明通常提供了用于制备放射性碘化3-氟丙基-去-β-CIT的方法。具体而言，该过程使用芳基硅烷中间体，从而避免使用六甲基锡，减少以前从去水基甲基植物碱制备放射性碘化3-氟丙基-去-β-CIT所需的步骤数量。该发明还涉及利用3-氟丙醛对去幽梗烷烃进行烷基化，形成相应的N-(3-氟丙基)类似物。
• US9339565B2
  申请人：——

  公开号：US9339565B2

  公开（公告）日：2016-05-17
• Synthesis of 3-arylecgonine analogs as inhibitors of cocaine binding and dopamine uptake
  作者：Richard H. Kline、Jeremy Wright、Kristine M. Fox、Mohyee E. Eldefrawi

  DOI：10.1021/jm00169a036

  日期：1990.7

  3-Arylecgonine analogues were synthesized and characterized by 1H and 13C NMR, IR, and MS. The compounds were synthesized as racemates from cycloheptatriene-7-carboxylic acid or enantiomerically from (-)-cocaine. These analogues were tested for their ability to inhibit [3H]cocaine binding to bovine striatal tissue and to inhibit [3H]dopamine uptake into striatal synaptosomes. Methyl (1RS-2-exo-3-exo)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-ca rboxylate was the most potent analogue. IC50 values for inhibition of cocaine binding and dopamine uptake were 20 and 100 nM, respectively. The racemates and the 1R isomers were equally potent inhibitors of binding and uptake. Methyl (1RS-2-endo-3-exo)-3-(2,4-dinitrophenyl)-8-methyl-8-azabicyclo[3.2 .1]octane- 2-carboxylate was the least potent. IC50 for inhibition of both binding and uptake was 40 microM.