1,2,5-trimethoxy-3-(1-propenyl)benzene | 5273-82-5

• 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-(1-propenyl)benzene
• 英文别名: (E)-1-(2,3,5-trimethoxyphenyl)prop-1-ene；(E)-3-prop-1'-enyl-1,2,5-trimethoxybenzene；(E)-1,2,5-trimethoxy-3-(prop-1-en-1-yl)benzene；trans-2,3,5-Trimethoxy-1-propenyl-benzol；1,2,5-trimethoxy-3-[(E)-prop-1-enyl]benzene
• CAS: 5273-82-5
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: VWEDKGLQURJRPK-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 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-(1-propenyl)benzene 在 吡啶 、 lithium aluminium tetrahydride 、 四硝基甲烷 作用下， 以 丙酮 为溶剂， 生成 2,3,5-三甲氧基安非他命
  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：

  2-hydroxy-3,5-dimethoxybenzaldehyde 在 potassium tert-butylate 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 1,2,5-trimethoxy-3-(1-propenyl)benzene
  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

• Role of the methoxy group in product formation via TiCl4 promoted 4-phenyldioxolane isomerizationsons
  作者：Ivan Robert Green、Natasha October

  DOI：10.3998/ark.5550190.0011.206

  日期：——

  The product distribution obtained from the TiCl4 initiated intramolecular isomerizations of 4methoxyphenyland trimethoxyphenyldioxolanes at -78 C, -30 C and 0 C provided insights into the important regiochemical role played by these groups in such Mukaiyamatype rearrangements through their resonance effects on the aryl ring of the dioxolanes.

  从 TiCl4 引发的 4-甲氧基苯基和三甲氧基苯基二氧戊环在 -78°C、-30°C 和 0°C 的分子内异构化获得的产物分布提供了对这些基团在此类 Mukaiyama 型重排中发挥的重要区域化学作用的见解，通过它们对二氧戊环的芳环的共振作用.
• 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。
• 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.