1-Allyl-2,3,4-trimethoxybenzene | 5273-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-Allyl-2,3,4-trimethoxybenzene
• 英文别名: 2,3,4-Trimethoxyallylbenzene；2,3,4-Trimethoxy-1-allyl-benzol；1,2,3-trimethoxy-4-prop-2-enylbenzene
• CAS: 5273-88-1
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: VZNVINHATUJPSB-UHFFFAOYSA-N

物化性质

• 沸点：
  127-132 °C(Press: 3 Torr)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  1-Allyl-2,3,4-trimethoxybenzene 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 1,2,3-trimethoxy-4-propenylbenzene
  参考文献：
  名称：

  SYNTHESIS OF THE TRIMETHOXYPHENYLPROPENES

  摘要：

  不可用。

  DOI：

  10.1139/v65-478
• 作为产物：
  描述：

  2,3-二甲氧基苯酚 在 氯化二乙基铝 、 potassium carbonate 作用下， 以 正己烷 、 丙酮 为溶剂， 反应 1.0h， 生成 1-Allyl-2,3,4-trimethoxybenzene
  参考文献：
  名称：

  选择性克莱森重排和碘化反应合成多氧化烯丙基苯酚衍生物

  摘要：

  从商业或合成的苯酚开始制备烯丙基芳基醚和烯丙基苯酚衍生物。进行威廉姆森反应或Et 2 AlCl催化的克莱森重排以获得多加氧分子。然后通过甲基化，碘环化或亲电子碘化碘化对枢轴烯丙基苯酚进行改性，从而以良好或优异的收率得到多氧化衍生物。此外，还研究了它们对革兰氏阳性和革兰氏阴性细菌的抗菌性能。

  DOI：

  10.1016/j.tetlet.2016.07.079

文献信息

• 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
• Discovery of structurally simplified analogs of colchicine as an immunosuppressant
  作者：Dong-Jo Chang、Wan-Joo Kim

  DOI：10.1016/j.bmcl.2014.05.007

  日期：2014.7

  We have discovered a new class of colchicine-derived therapeutic agents for immune diseases including rejection of organ-transplantation and autoimmune disease. Compound 2, which had been developed to overcome poor pharmacokinetic properties of compound 1, a first-generation colchicine analog, turned out to show toxicity such as intestinal toxicity and loss of weight during in vivo tests. The deletion of 7-carboxamide group and middle ring-truncation in colchicine allowed us to have structurally simplified analogs with strong immunosuppressive activity. Herein, we report non-alkaloid tricyclic compound 7 and 12 as immunosuppressants which exhibited a strong immunosuppressive in vivo efficacy on the T-dependent antibody response, the Zymosan A-induced arthritis model and the Carrageenan-induced edema model. Compound 7 and 12 revealed less toxicity than the previous lead compound 2, and their minimum lethal doses (MLD) were proved to exceed 100 mg/kg. (C) 2014 Elsevier Ltd. All rights reserved.
• The Synthesis of Naturally Occurring C₆-C₃and C₆-C₃-C₆Substances by the Use of Low-Valent Nickel-Mediated Grignard Reactions
  作者：Ernest Wenkert、João Battista Fernandes、Enrique L. Michelotti、Charles S. Swindell

  DOI：10.1055/s-1983-30474

  日期：——
• Palladium-Catalyzed <i>meta</i>-C–H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group
  作者：Siqiang Fang、Xiaobing Wang、Fucheng Yin、Pei Cai、Huali Yang、Lingyi Kong

  DOI：10.1021/acs.orglett.9b00433

  日期：2019.3.15

  The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including H-1 NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.
• Devakumar, C.; Mukerjee, S. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 368 - 372
  作者：Devakumar, C.、Mukerjee, S. K.

  DOI：——

  日期：——

表征谱图