8-methoxy-3,4-dihydro-3-(di-n-propylamino)-2H-1-benzopyran | 110927-06-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-methoxy-3,4-dihydro-3-(di-n-propylamino)-2H-1-benzopyran
• 英文别名: 8-methoxy-3,4-dihydro-3-(dipropylamino)-2H-1-benzopyran；N,N-di-n-propyl-8-methoxy-3-chromanamine；8-methoxy-N,N-dipropyl-3,4-dihydro-2H-chromen-3-amine
• CAS: 110927-06-5；137279-60-8；137279-61-9
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: OFIOYUDTGQMDME-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
• 沸点：
  369.1±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-methoxy-3,4-dihydro-3-(di-n-propylamino)-2H-1-benzopyran 生成 N,N-bis(1,1,2,2,3,3,3-heptatritiopropyl)-8-methoxy-3,4-dihydro-2H-chromen-3-amine
  参考文献：
  名称：

  PICHAT, L., SYNTH. AND APPL. ISOTOPICALLY LABELLED COMPOUNDS, 1988: PROC. 3RD INT. SY+

  摘要：

  DOI：
• 作为产物：
  描述：

  8-甲氧基-2H-苯并吡喃-3-甲腈 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 叠氮磷酸二苯酯 、 氢气 、 三乙胺 作用下， 以 甲醇 、 戊醇 、 溶剂黄146 为溶剂， 80.0~85.0 ℃ 、344.73 kPa 条件下， 反应 13.5h， 生成 8-methoxy-3,4-dihydro-3-(di-n-propylamino)-2H-1-benzopyran
  参考文献：
  名称：

  6- and 8-Hydroxy-3,4-dihydro-3-(dipropylamino)-2H-1-benzopyrans. Dopamine agonists with autoreceptor selectivity

  摘要：

  The dopamine agonist profiles of 3,4-dihydro-3-(3-dipropylamino)-2H-1-benzopyran-6- and -8-ol (4 and 5, respectively) were examined. Both 4 and 5 exhibited greater relative affinity for receptors labeled with the dopamine agonist ligand [3H]propylnorapomorphine than for those labeled with the dopamine antagonist ligand [3H]haloperidol. Both compounds attenuated the stimulation of brain dopamine synthesis caused by gamma-butyrolactone (GBL) and decreased the firing rate of substantia nigra dopamine neurons in rats. This profile of activity, together with the ability of the dopamine antagonist haloperidol to reverse the inhibition of dopamine neuronal firing, indicate that both compounds are brain dopamine agonists.

  DOI：

  10.1021/jm00398a032

文献信息

• Methoxy and hydroxy derivatives of 3,4-dihydro-3-(di-n-propylamino)-2H-1-benzopyrans: new synthesis and dopaminergic activity
  作者：M Al Neirabeyeh、D Reynaud、T Podona、L Ou、C Perdicakis、G Coudert、G Guillaumet、L Pichat、A Gharib、N Sarda

  DOI：10.1016/0223-5234(91)90145-d

  日期：1991.7

  The synthesis of methoxy and hydroxy derivatives of 3,4-dihydro-3-(di-n-propylamino)-2H-1-benzopyran from readily available or commercial omicron-hydroxybenzaldehydes is described in six steps. The enantiomers of 8-hydroxy-3,4-dihydro-3-(di-n-propylamino)-2H-1-benzopyran 1b have been resolved. It is shown that the compound (-)-1b is a more selective D-2 agonist, compared to apomorphine.
• N,N -Disubstituted Aminomethyl Benzofuran Derivatives: Synthesis and Preliminary Binding Evaluation
  作者：Sophie Boyé、Bruno Pfeiffer、Pierre Renard、Marie-Claire Rettori、Gérald Guillaumet、Marie-Claude Viaud

  DOI：10.1016/s0968-0896(98)00239-9

  日期：1999.2

  A series of new N-substituted 2,3-dihydro-2-aminomethyl-2H-1-benzofuran derivatives was prepared and evaluated for affinity at 5-HT1A, 5-HT2A, 5-HT2C, 5-H-3, D-2, and D-3 receptors. Compound 9, 8-[4-[N-propyl-N-(7-hydroxy-2,3-dihydro-2h-1-benzofuran-2-yl)methyl]aminobutyl]-8-azaspiro[4,5]decane-7,9-dione, bound at 5-HT1A sites with nanomolar affinity (IC50 = 1.5 nM) and high selectivity over 5-HT2A, 5-HT2C, 5-HT3, D-2, and D-3 receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.
• PICHAT, L., SYNTH. AND APPL. ISOTOPICALLY LABELLED COMPOUNDS, 1988: PROC. 3RD INT. SY+
  作者：PICHAT, L.

  DOI：——

  日期：——
• THORBERG, SETH-OLOV;HALL, HAKAN;AKESSON, CHRISTINA;SVENSSON, KJELL;NILSSO+, ACTA PHARM. SUEC., 24,(1987) N 4, 169-182
  作者：THORBERG, SETH-OLOV、HALL, HAKAN、AKESSON, CHRISTINA、SVENSSON, KJELL、NILSSO+

  DOI：——

  日期：——
• WISE, LAWRENCE D.;DEWALD, HORACE A.;HAWKINS, ELMA S.;REYNOLDS, DONNA M.;H+, J. MED. CHEM., 31,(1988) N 3, 688-691
  作者：WISE, LAWRENCE D.、DEWALD, HORACE A.、HAWKINS, ELMA S.、REYNOLDS, DONNA M.、H+

  DOI：——

  日期：——