(4aR,10aR)-6-methoxy-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinoline-1-carboxylic acid tert-butyl ester | 1522181-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (4aR,10aR)-6-methoxy-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinoline-1-carboxylic acid tert-butyl ester
• CAS: 1522181-58-3
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: OZWSHQLHCZUBNK-GDBMZVCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4aR,10aR)-6-methoxy-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinoline-1-carboxylic acid tert-butyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 Trans-1,2,3,4,4a,5,10,10a-octahydro-N-methyl-6-methoxybenzo[g]quinoline
  参考文献：
  名称：

  Synthesis and SAR study of a novel series of dopamine receptor agonists

  摘要：

  The synthesis of a novel series of dopamine receptor agonists are described as well as their in vitro potency and efficacy on dopamine D-1 and D-2 receptors. This series was designed from pergolide and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g] quinolin-6-ol (PHBQ) and resulted in the synthesis of (2R,4aR,10aR)-2-methylsulfanylmethyl-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazin-9-ol (compound 27), which has a D-1 and D-2 receptor profile similar to that of the most recently approved drug for Parkinson's disease, rotigotine. (C)2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.012
• 作为产物：
  描述：

  6-methoxy-2,3,4,4a,5,10-hexahydrobenzo-quinolinium chloride 在 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 为溶剂， 反应 72.5h， 生成 (4aR,10aR)-6-methoxy-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinoline-1-carboxylic acid tert-butyl ester 、 (4aS,10aS)-6-methoxy-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinoline-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and SAR study of a novel series of dopamine receptor agonists

  摘要：

  The synthesis of a novel series of dopamine receptor agonists are described as well as their in vitro potency and efficacy on dopamine D-1 and D-2 receptors. This series was designed from pergolide and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g] quinolin-6-ol (PHBQ) and resulted in the synthesis of (2R,4aR,10aR)-2-methylsulfanylmethyl-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazin-9-ol (compound 27), which has a D-1 and D-2 receptor profile similar to that of the most recently approved drug for Parkinson's disease, rotigotine. (C)2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.012