2-(4-hydroxyphenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-6,7-methylendioxy-1,2,3,4-tetrahydroquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(4-hydroxyphenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-6,7-methylendioxy-1,2,3,4-tetrahydroquinoline
• 英文别名: DM380；2-(4-hydroxyphenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroquinoline；4-[(6R,7R,8S)-6-(4-hydroxyphenyl)-7-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-8-yl]-2-methoxyphenol
• 化学式: C₂₄H₂₃NO₅
• 分子量: 405.45
• InChiKey: YGQLHXKPDHMTSC-YQQIJLMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丁香酚 在 10% KOH/alumina 作用下， 以 乙腈 为溶剂， 反应 8.33h， 生成 2-(4-hydroxyphenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-6,7-methylendioxy-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Highly diastereoselective synthesis of new heterolignan-like 6,7-methylendioxy-tetrahydroquinolines using the clove bud essential oil as raw material

  摘要：

  The diastereoselective synthesis toward novel heterolignan-like 2-aryl-4-(4-hydroxy-3-methoxyphenyl)6,7-methylendioxy-1,2,3,4-tetrahydroquinolines using for the first time clove bud essential oil as a renewable material was carried out. The synthetic protocol consisted of the hydrodistillation of dried flower buds, the solid base-catalyzed isomerization of the obtained essential oil enriched with eugenol in order to give isoeugenol and its participation, as a chemical reagent (dienophile) in the BF3.OEt2-catalyzed three component Povarov reaction, without previous purification. Final products were obtained as racemic mixtures of new trans-2,4-diaryl-r-3-Me-1,2,3,4-tetrahydroquinolines in moderate to good yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.083

文献信息

• Synthesis and cytotoxic evaluation of novel 2-aryl-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-6,7-methylendioxy-1,2,3,4-tetrahydroquinolines, podophyllotoxin-like molecules
  作者：Vladimir V. Kouznetsov、Diego R. Merchan-Arenas、Veronica Tangarife-Castaño、Julieth Correa-Royero、Liliana Betancur-Galvis

  DOI：10.1007/s00044-015-1486-6

  日期：2016.3

  Diverse 2-aryl-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-6,7-methylendioxy-1,2,3,4-tetrahydroquinolines (DM series) were synthesized using three-component reaction of 3,4-methylendioxyaniline, benzaldehydes and isoeugenol. Purified and characterized tetrahydroquinoline molecules were tested in vitro for potential antitumor and cytotoxic activities. It was observed a strong relationship between selective cytotoxic activity on U937 and HeLa cells and the substitutions presented in aryl ring of position C-2 of the synthesized tetrahydroquinoline derivatives. Tested molecules, called DM108, DM116 and DM118, resulted in active compounds having a greater SI compared with colchicine and doxorubicin, reference compounds.
• Highly diastereoselective synthesis of new heterolignan-like 6,7-methylendioxy-tetrahydroquinolines using the clove bud essential oil as raw material
  作者：Diego R. Merchan Arenas、Fernando A. Rojas Ruíz、Vladimir V. Kouznetsov

  DOI：10.1016/j.tetlet.2011.01.083

  日期：2011.3

  The diastereoselective synthesis toward novel heterolignan-like 2-aryl-4-(4-hydroxy-3-methoxyphenyl)6,7-methylendioxy-1,2,3,4-tetrahydroquinolines using for the first time clove bud essential oil as a renewable material was carried out. The synthetic protocol consisted of the hydrodistillation of dried flower buds, the solid base-catalyzed isomerization of the obtained essential oil enriched with eugenol in order to give isoeugenol and its participation, as a chemical reagent (dienophile) in the BF3.OEt2-catalyzed three component Povarov reaction, without previous purification. Final products were obtained as racemic mixtures of new trans-2,4-diaryl-r-3-Me-1,2,3,4-tetrahydroquinolines in moderate to good yields. (C) 2011 Elsevier Ltd. All rights reserved.