1,2,5-trimethoxy-3-allylbenzene | 5273-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2,5-trimethoxy-3-allylbenzene
• 英文别名: 2,3,5-trimethoxyallylbenzene；1,3,5-trimethoxy-3-prop-2-enylbenzene；2,3,5-Trimethoxy-1-allyl-benzol；2,4-dimethoxy-6-allylanisole；1-Allyl-2,3,5-trimethoxybenzene；1,2,5-trimethoxy-3-prop-2-enylbenzene
• CAS: 5273-91-6
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: PVKIMIQBQMFUFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,5-trimethoxy-3-allylbenzene 在 咪唑 、 sodium tetrahydroborate 、 potassium tert-butylate 、 碘 、 臭氧 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 C₁₈H₂₆O₄
  参考文献：
  名称：

  abinetanee和icetexane型二萜的三环核的快速构建

  摘要：

  摘要以烷基化和酸催化的环化为关键步骤，从一个常见的中间体中简短合成了abietane和icetexane型二萜的三环6-6-6和6-7-6环系统。

  DOI：

  10.1016/j.cclet.2011.01.009
• 作为产物：
  描述：

  4-(烯丙氧基)-3-甲氧基苯甲醛 在 氢氧化钾 、 双氧水 作用下， 以 sodium hydroxide 、 水 为溶剂， 反应 33.0h， 生成 1,2,5-trimethoxy-3-allylbenzene
  参考文献：
  名称：

  Wolska; Poplawski; Lozowicka, Polish Journal of Chemistry, 1998, vol. 72, # 10, p. 2331 - 2341

  摘要：

  DOI：

文献信息

• Towards an asymmetric synthesis of the bacterial peptide deformylase (PDF) inhibitor fumimycin
  作者：Caroline E. Hartmann、Patrick J. Gross、Martin Nieger、Stefan Bräse

  DOI：10.1039/b916372g

  日期：——

  Studies towards the synthesis of the bacterial peptide deformylase (PDF) inhibitor fumimycin are reported. The synthetic approach features an organocatalytic access to the α,α-disubstituted amino acid unit and results in the synthesis of an advanced intermediate which already contains all functionalities of fumimycin.

  报道了合成细菌肽去甲酰基化酶（PDF）抑制剂富米霉素的研究。合成方法的特征是有机催化接近α，α-二取代的氨基酸单元，并导致合成高级中间体，该中间体已经包含了泛霉素的所有功能。
• SYNTHESIS OF THE TRIMETHOXYPHENYLPROPENES
  作者：Alexander T. Shulgin

  DOI：10.1139/v65-478

  日期：1965.12.1

  not available

  不可用。
• Structure-activity relationships of phenylpropanoids as growth inhibitors of the green alga Selenastrum capricornutum
  作者：Marina Della Greca、Pietro Monaco、Antonino Pollio、Lucio Previtera

  DOI：10.1016/0031-9422(92)80425-e

  日期：1992.12
• 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.