(+/-)-5-((2-methoxyethoxy)methoxy)-2-hydroxy-4,4-dimethylcyclohex-1-enecarboxylic acid methyl ester | 888325-30-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-5-((2-methoxyethoxy)methoxy)-2-hydroxy-4,4-dimethylcyclohex-1-enecarboxylic acid methyl ester
• 英文别名: Methyl 2-hydroxy-5-(2-methoxyethoxymethoxy)-4,4-dimethylcyclohexene-1-carboxylate
• CAS: 888325-30-2
• 化学式: C₁₄H₂₄O₆
• 分子量: 288.341
• InChiKey: LUVDVWVUDBJSHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-5-((2-methoxyethoxy)methoxy)-2-hydroxy-4,4-dimethylcyclohex-1-enecarboxylic acid methyl ester 在 双(三甲基硅烷基)氨基钾 、 四甲基胍 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 57.25h， 生成 (+/-)-(9Z)-7-((2-methoxyethoxy)methoxy)-9-ethylidene-3,6,6-trimethylbicyclo[3.3.1]non-3-ene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Discovery of Huperzine A−Tacrine Hybrids as Potent Inhibitors of Human Cholinesterases Targeting Their Midgorge Recognition Sites

  摘要：

  We describe herein the development of novel huperzine A-tacrine hybrids characterized by 3-methylbicyclo[3.3.1] non-3-ene scaffolds. These compounds were specifically designed to establish tight interactions, through different binding modes, with the midgorge recognition sites of human acetylcholinesterase (hAChE: Y72, D74) and human butyrylcholinesterase (hBuChE: N68, D70) and their catalytic or peripheral sites. Compounds 5a-c show a markedly improved biological profile relative to tacrine and huperzine A.

  DOI：

  10.1021/jm060257t
• 作为产物：
  描述：

  7,7-dimethyl-1,4-dioxaspiro[4.5]decan-8-one 在 盐酸 、 sodium tetrahydroborate 、 potassium hydride 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 80.0h， 生成 (+/-)-5-((2-methoxyethoxy)methoxy)-2-hydroxy-4,4-dimethylcyclohex-1-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Discovery of Huperzine A−Tacrine Hybrids as Potent Inhibitors of Human Cholinesterases Targeting Their Midgorge Recognition Sites

  摘要：

  We describe herein the development of novel huperzine A-tacrine hybrids characterized by 3-methylbicyclo[3.3.1] non-3-ene scaffolds. These compounds were specifically designed to establish tight interactions, through different binding modes, with the midgorge recognition sites of human acetylcholinesterase (hAChE: Y72, D74) and human butyrylcholinesterase (hBuChE: N68, D70) and their catalytic or peripheral sites. Compounds 5a-c show a markedly improved biological profile relative to tacrine and huperzine A.

  DOI：

  10.1021/jm060257t