5-methoxy-2-methyl-6-(2-nitro-1-propenyl)-2,3-dihydrobenzofuran | 85258-21-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5-methoxy-2-methyl-6-(2-nitro-1-propenyl)-2,3-dihydrobenzofuran
• 英文别名: 5-methoxy-2-methyl-6-[(E)-2-nitroprop-1-enyl]-2,3-dihydro-1-benzofuran
• CAS: 85258-21-5
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: DBZWDPBKQWJZKV-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-methyl-6-(2-nitro-1-propenyl)-2,3-dihydrobenzofuran 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Synthesis and evaluation of 2,3-dihydrobenzofuran analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats

  摘要：

  Two analogues, 6-(2-aminopropyl)-5-methoxy-2,3-dihydrobenzofuran and 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran, of the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) were synthesized and tested in the two-lever drug discrimination paradigm. In rats trained to discriminate saline from LSD tartrate (0.08 mg/kg), stimulus generalization occurred to both of the 2,3-dihydrobenzofuran analogues but at doses more than 10-fold higher than for DOM. A possible explanation for this dramatic attenuation of LSD-like activity could involve a highly directional electrophilic binding site on the receptor that cannot accept the orientation of the unshared electron pairs on the heterocyclic oxygen atom in the benzofurans.

  DOI：

  10.1021/jm00152a022
• 作为产物：
  描述：

  2,3-dihydro-5-methoxy-2-methylbenzofuran 在 ammonium acetate 、 三氯氧磷 作用下， 反应 3.5h， 生成 5-methoxy-2-methyl-6-(2-nitro-1-propenyl)-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Synthesis and evaluation of 2,3-dihydrobenzofuran analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats

  摘要：

  Two analogues, 6-(2-aminopropyl)-5-methoxy-2,3-dihydrobenzofuran and 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran, of the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) were synthesized and tested in the two-lever drug discrimination paradigm. In rats trained to discriminate saline from LSD tartrate (0.08 mg/kg), stimulus generalization occurred to both of the 2,3-dihydrobenzofuran analogues but at doses more than 10-fold higher than for DOM. A possible explanation for this dramatic attenuation of LSD-like activity could involve a highly directional electrophilic binding site on the receptor that cannot accept the orientation of the unshared electron pairs on the heterocyclic oxygen atom in the benzofurans.

  DOI：

  10.1021/jm00152a022

文献信息

• KOVTUNENKO, V. A.;KISEL, V. M.;TYLTIN, A. K.;BABICHEV, F. S., DOKL. AN YCCP, 1983, N 1, 24-30
  作者：KOVTUNENKO, V. A.、KISEL, V. M.、TYLTIN, A. K.、BABICHEV, F. S.

  DOI：——

  日期：——
• NICHOLS, D. E.;HOFFMAN, A. J.;OBERLENDER, R. A.;RIGGS, R. M., J. MED. CHEM., 1986, 29, N 2, 302-304
  作者：NICHOLS, D. E.、HOFFMAN, A. J.、OBERLENDER, R. A.、RIGGS, R. M.

  DOI：——

  日期：——
• Synthesis and evaluation of 2,3-dihydrobenzofuran analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats
  作者：David E. Nichols、Andrew J. Hoffman、Robert A. Oberlender、Robert M. Riggs

  DOI：10.1021/jm00152a022

  日期：1986.2

  Two analogues, 6-(2-aminopropyl)-5-methoxy-2,3-dihydrobenzofuran and 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran, of the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) were synthesized and tested in the two-lever drug discrimination paradigm. In rats trained to discriminate saline from LSD tartrate (0.08 mg/kg), stimulus generalization occurred to both of the 2,3-dihydrobenzofuran analogues but at doses more than 10-fold higher than for DOM. A possible explanation for this dramatic attenuation of LSD-like activity could involve a highly directional electrophilic binding site on the receptor that cannot accept the orientation of the unshared electron pairs on the heterocyclic oxygen atom in the benzofurans.