1,2,3,4-tetrahydro-2,3-methano-3,5-dimethoxy-2-methylnaphthalene | 105372-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydro-2,3-methano-3,5-dimethoxy-2-methylnaphthalene
• 英文别名: Beldlcxuezefll-uhfffaoysa-；1a,3-dimethoxy-7a-methyl-2,7-dihydro-1H-cyclopropa[b]naphthalene
• CAS: 105372-37-0
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: BELDLCXUEZEFLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-2,3-methano-3,5-dimethoxy-2-methylnaphthalene 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以62%的产率得到8-methoxy-3,3-dimethyl-2-tetralone
  参考文献：
  名称：

  Syntheses of 5-, 7-, and 8-methoxy-3-methyl-2-tetralones

  摘要：

  DOI：

  10.1021/jo00376a038
• 作为产物：
  描述：

  1,7-二甲氧基-6-甲基萘 在 diethylzinc 、 sodium 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 1,2,3,4-tetrahydro-2,3-methano-3,5-dimethoxy-2-methylnaphthalene
  参考文献：
  名称：

  Central dopaminergic and 5-hydroxytryptaminergic effects of C(3)-methylated derivatives of 8-hydroxy-2-(di-n-propylamino)tetralin

  摘要：

  A number of stereochemically well defined C3-methylated derivatives of the potent 5-hydroxytryptamine (5-HT) receptor agonist 8-hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT) have been synthesized, and their stereochemical characteristics have been studies by use of NMR spectroscopy, X-ray crystallography, and molecular mechanics calculations. The compounds were tested for activity at central 5-HT and dopamine (DA) receptors, by use of biochemical and behavioral tests in rats. In addition, the ability of the cis- and trans-8-hydroxy-3-methyl-2-(di-n-propylamino)tetralins (15 and 11) to displace [3H]-8-OH-DPAT from 5-HT1A binding sites was evaluated. The stereoselectivity of the interaction of 11 and 15 with 5-HT receptors was much greater than that of 8-OH-DPAT. Observed rank order of potencies in the 5-HT1A binding assay corresponds to that in the in vivo biochemical assay.

  DOI：

  10.1021/jm00401a012

文献信息

• Syntheses of 5-, 7-, and 8-methoxy-3-methyl-2-tetralones
  作者：Anette M. Johansson、Charlotta Mellin、Uli Hacksell

  DOI：10.1021/jo00376a038

  日期：1986.12
• JOHANSSON A. M.; MELLIN CH.; HACKSELL U., J. ORG. CHEM., 51,(1986) N 26, 5252-5258
  作者：JOHANSSON A. M.、 MELLIN CH.、 HACKSELL U.

  DOI：——

  日期：——
• Central dopaminergic and 5-hydroxytryptaminergic effects of C(3)-methylated derivatives of 8-hydroxy-2-(di-n-propylamino)tetralin
  作者：Charlotta Mellin、Lena Bjoerk、Anders Karlen、Anette M. Johansson、Staffan Sundell、Lennart Kenne、David L. Nelson、Nils Erik Anden、Uli Hacksell

  DOI：10.1021/jm00401a012

  日期：1988.6

  A number of stereochemically well defined C3-methylated derivatives of the potent 5-hydroxytryptamine (5-HT) receptor agonist 8-hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT) have been synthesized, and their stereochemical characteristics have been studies by use of NMR spectroscopy, X-ray crystallography, and molecular mechanics calculations. The compounds were tested for activity at central 5-HT and dopamine (DA) receptors, by use of biochemical and behavioral tests in rats. In addition, the ability of the cis- and trans-8-hydroxy-3-methyl-2-(di-n-propylamino)tetralins (15 and 11) to displace [3H]-8-OH-DPAT from 5-HT1A binding sites was evaluated. The stereoselectivity of the interaction of 11 and 15 with 5-HT receptors was much greater than that of 8-OH-DPAT. Observed rank order of potencies in the 5-HT1A binding assay corresponds to that in the in vivo biochemical assay.

表征谱图