4-(1,3-dioxolan-2-yl)-6-[N-(tBOC)-N-methylamino]hexan-1-al | 556811-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 4-(1,3-dioxolan-2-yl)-6-[N-(tBOC)-N-methylamino]hexan-1-al
• 英文别名: tert-butyl N-[3-(1,3-dioxolan-2-yl)-6-oxohexyl]-N-methylcarbamate
• CAS: 556811-98-4
• 化学式: C₁₅H₂₇NO₅
• 分子量: 301.383
• InChiKey: UAWKRWCLRWQYQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate 、 4-(1,3-dioxolan-2-yl)-6-[N-(tBOC)-N-methylamino]hexan-1-al 反应 0.5h， 以93%的产率得到(3aR,4S,11bS)-3-Benzyl-4-[4-(tert-butoxycarbonyl-methyl-amino)-2-[1,3]dioxolan-2-yl-butyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 18-Methoxycoronaridine Congeners. Potential Antiaddiction Agents

  摘要：

  Variation of the methoxycarbonyl and C-18 substituents of the antiaddictive compound 18-methoxycoronaridine, and contraction of its isoquinuclidine ring segment, provided 15 congeners for SAR evaluation at opioid and alpha3beta4 nicotinic acetylcholine receptors. The opioid activities were relatively low, and the alpha3beta4 nicotinic acetylcholine receptor activities were found to correlate with in vivo antiaddictive activities.

  DOI：

  10.1021/jm020562o
• 作为产物：
  描述：

  烯丙基丙二酸二乙酯 在 palladium on activated charcoal 、 N,N-二甲基甲酰胺 lithium aluminium tetrahydride 、 三甲基氯硅烷 、 2-甲基-2-丁烯 、 草酰氯 、 硼烷 、 氢气 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， -78.0~180.0 ℃ 、101.33 kPa 条件下， 反应 180.5h， 生成 4-(1,3-dioxolan-2-yl)-6-[N-(tBOC)-N-methylamino]hexan-1-al
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 18-Methoxycoronaridine Congeners. Potential Antiaddiction Agents

  摘要：

  Variation of the methoxycarbonyl and C-18 substituents of the antiaddictive compound 18-methoxycoronaridine, and contraction of its isoquinuclidine ring segment, provided 15 congeners for SAR evaluation at opioid and alpha3beta4 nicotinic acetylcholine receptors. The opioid activities were relatively low, and the alpha3beta4 nicotinic acetylcholine receptor activities were found to correlate with in vivo antiaddictive activities.

  DOI：

  10.1021/jm020562o

文献信息

• Synthesis and Biological Evaluation of 18-Methoxycoronaridine Congeners. Potential Antiaddiction Agents
  作者：Martin E. Kuehne、Liwen He、Patrick A. Jokiel、C. J. Pace、M. W. Fleck、I. M. Maisonneuve、Stanley D. Glick、Jean M. Bidlack

  DOI：10.1021/jm020562o

  日期：2003.6.1

  Variation of the methoxycarbonyl and C-18 substituents of the antiaddictive compound 18-methoxycoronaridine, and contraction of its isoquinuclidine ring segment, provided 15 congeners for SAR evaluation at opioid and alpha3beta4 nicotinic acetylcholine receptors. The opioid activities were relatively low, and the alpha3beta4 nicotinic acetylcholine receptor activities were found to correlate with in vivo antiaddictive activities.