1-(2,3,4-三甲氧基苯基)-1-丙醇 | 54440-47-0

• 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-(2,3,4-三甲氧基苯基)-1-丙醇
• 英文名称: 1-(2,3,4-trimethoxyphenyl)-1-propanol
• 英文别名: 1-(2,3,4-Trimethoxyphenyl)propan-1-ol
• CAS: 54440-47-0
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: XOICCVZNJKXXEC-UHFFFAOYSA-N

物化性质

• 沸点：
  340.8±42.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

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-(2,3,4-三甲氧基苯基)-1-丙醇 在 silica gel 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.05h， 以71%的产率得到1,2,3-trimethoxy-4-propenylbenzene
  参考文献：
  名称：

  An Effective System to Synthesize Hypolipidemic Active α-Asarone and Related Methoxylated (E)-Arylalkenes

  摘要：

  通过改进的Grignard反应，分两步制备了甲氧基化（E）-芳基烯烃（1a-1k）。该反应包括在无水乙醚和甲苯中反向加成烷基镁溴化物至苯甲醛（2a-2k），高产率地转化为芳基醇（3a-3k），随后在微波辐射下，根据芳香环上取代基的不同，利用硅胶进行脱水处理3-12分钟，得到具有降脂活性的α-细辛素（1a）及相关甲氧基化（E）-芳基烯烃（1b-1k）。

  DOI：

  10.1246/bcsj.77.2231
• 作为产物：
  描述：

  溴乙烷 、 2,3,4-三甲氧基苯甲醛 在 magnesium 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 2.0h， 以88%的产率得到1-(2,3,4-三甲氧基苯基)-1-丙醇
  参考文献：
  名称：

  An Effective System to Synthesize Hypolipidemic Active α-Asarone and Related Methoxylated (E)-Arylalkenes

  摘要：

  通过改进的Grignard反应，分两步制备了甲氧基化（E）-芳基烯烃（1a-1k）。该反应包括在无水乙醚和甲苯中反向加成烷基镁溴化物至苯甲醛（2a-2k），高产率地转化为芳基醇（3a-3k），随后在微波辐射下，根据芳香环上取代基的不同，利用硅胶进行脱水处理3-12分钟，得到具有降脂活性的α-细辛素（1a）及相关甲氧基化（E）-芳基烯烃（1b-1k）。

  DOI：

  10.1246/bcsj.77.2231

文献信息

• Neutral Ionic Liquid [hmim]Br as a Green Reagent and Solvent for the Mild and Efficient Dehydration of Benzyl Alcohols into (<i>E</i>)-Arylalkenes Under Microwave Irradiation
  作者：Rakesh Kumar、Abhishek Sharma、Naina Sharma、Vinod Kumar、Arun K. Sinha

  DOI：10.1002/ejoc.200800657

  日期：2008.11

  A mild and efficient, ionic-liquid-assisted, green protocol for the dehydration of benzyl alcohols into the corresponding (E)-arylalkenes under microwave irradiation has been developed. The method utilizes a neutral and recyclable ionic liquid (1-hexyl-3-methylimidazolium bromide) as a reagent and solvent to cleanly provide a wide range of olefins withoutthe need of harsh and expensive Bronsted/Lewis

  已经开发了一种温和高效、离子液体辅助的绿色方案，用于在微波辐射下将苄醇脱水成相应的 (E)-芳基烯烃。该方法利用中性和可回收的离子液体（1-己基-3-甲基咪唑溴化物）作为试剂和溶剂，清洁地提供范围广泛的烯烃，而无需苛刻且昂贵的布朗斯台德/路易斯酸。该方法扩展到将苯甲醇的乙酰化/苯甲酰化衍生物有效转化为其相应的 (E)-芳基烯烃。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Unexpected formation of aryl dialkyl carbinol as a side product from the reaction of methoxyarylaldehydes with Grignard reagents
  作者：Anuj Sharma、Bhupendra P. Joshi、Narendra P. Singh、Arun K. Sinha

  DOI：10.1016/j.tet.2005.10.051

  日期：2006.1

  In the attempted formation of secondary aryl alkyl carbinols from the reaction of methoxyarylaldehydes with Grignard reagents, aryl dialkyl carbinols were formed as unexpected side products. A mechanism for their formation is proposed.

  在尝试由甲氧基芳基醛与格利雅试剂反应形成仲芳基烷基甲醇时，形成了芳基二烷基甲醇，这是出乎意料的副产物。提出了形成它们的机制。
• 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.