1-(2,3,6-三甲氧基苯基)-1-丙醇 | 5556-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2,3,6-三甲氧基苯基)-1-丙醇
• 英文名称: 1-(2,3,6-trimethoxyphenyl)-1-propanol
• 英文别名: 1-(2,3,6-Trimethoxyphenyl)propan-1-ol
• CAS: 5556-78-5
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: GUWSBXZSFZXPMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,3,6-三甲氧基苯基)-1-丙醇 在 lithium aluminium tetrahydride 作用下， 生成 2,3,6-trimethoxyamphetamine
  参考文献：
  名称：

  六个三甲氧基苯基异丙基胺（三甲氧基苯异丙胺）。

  摘要：

  DOI：

  10.1021/jm00321a058
• 作为产物：
  描述：

  1,2,4-三甲氧基苯 、 丙醛 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.25h， 以56.7%的产率得到1-(2,3,6-三甲氧基苯基)-1-丙醇
  参考文献：
  名称：

  α-细辛脑衍生物的合成、抗癫痫作用和构效关系：所选衍生物的体外和体内神经保护作用

  摘要：

  在本研究中，我们使用 PTZ 诱导的癫痫模型比较了 α-细辛脑衍生物的抗癫痫作用，以探索其结构-活性关系。我们的研究表明，苯环 3,4,5-位上的供电子甲氧基可增加抗癫痫效力，但其他基团放置在不同位置会降低活性。此外，在烯丙基部分中，烯丙基或1-丁烯基与苯环共轭时可达到最佳活性。化合物5和19对体外（细胞）和体内（小鼠）模型的癫痫表现出更好的神经保护作用。该研究为进一步探索和应用这些化合物作为潜在的抗癫痫药物提供了有价值的数据。

  DOI：

  10.1016/j.bioorg.2021.105179

文献信息

• Feeding-deterrent activity of ?-asarone isomers against some stored Coleoptera
  作者：Janusz Pop?awski、Bo?ena ?ozowicka、Alina T Dubis、Barbara Lachowska、Zbigiew Winiecki、Jan Nawrot

  DOI：10.1002/(sici)1526-4998(200006)56:6<560::aid-ps171>3.0.co;2-x

  日期：2000.6

  All isomers of alpha-asarone [(E)-4-prop-1-enyl-1,2,5-trimethoxybenze] were tested for their feeding deterrent activity against adults of Sitophilus granarius and Tribolium confusum and larvae of Trogoderma granarium and Tribolium confusum. (E)-2-prop-1-enyl-1,3, 5-trimethoxybenzene exhibited the strongest deterrent activity against all the species tested. The total coefficients of deterrency for this compound were 140.6 and 169.7 for Tribolium confusum adults and larvae, respectively, and 144.9 and 104.6 for larvae of Trogoderma granarium and adults of Sitophilus granarius, respectively. (C) 2000 Society of Chemical Industry.
• Synthesis and Hypolipidemic and Antiplatelet Activities of α-Asarone Isomers in Humans (in Vitro), Mice (in Vivo), and Rats (in Vivo)
  作者：Janusz Popławski、Bożena Łozowicka、Alina T. Dubis、Barbara Lachowska、Stanisław Witkowski、Danuta Siluk、Jacek Petrusewicz、Roman Kaliszan、Jacek Cybulski、Małgorzata Strzałkowska、Zdzisław Chilmonczyk

  DOI：10.1021/jm000905n

  日期：2000.10.1

  yA series of alpha-asarone isomers was synthesized and investigated for their hypolipidemic and antiplatelet activity. Considering the hypolipidemic activity in rats at a dose of 80 mg/kg/day, some isomers were more potent than clofibrate at 150 mg/kg. Compound 3 was one of the most active agents elevating the HDL cholesterol level by 56% and lowering the LDL cholesterol level by 46.8% in rats after 7 days of administration. The activities of the platelet aggregation test in vitro were significant but lower than those of the reference substances (indomethacine and acetylsalicylic add). In the pulmonary thromboembolic in vivo test in mice, two compounds (alpha-asarone (6) and compound 4) produced significant anti thrombotic effects at 100 mg/kg, namely 44% and 52% protection against lung microembolia, respectively. alpha-Asarone derivatives form a new group of potential hypolipidemic and/or antithrombotic agents. The compounds 3, 4, and 6 may serve as lead substances whose structural modifications may result in original drugs.