2-allyloxy-1,4-dimethoxybenzene | 591249-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-allyloxy-1,4-dimethoxybenzene
• 英文别名: 1,4-Dimethoxy-2-prop-2-enoxybenzene
• CAS: 591249-40-0
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: RYYFJOVREHGXHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2-allyloxy-1,4-dimethoxybenzene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 [RuHCl(CO)(PPh₃)₃] 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 22.67h， 生成 4,7-dimethoxybenzofuran
  参考文献：
  名称：

  An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans

  摘要：

  Twelve substituted benzofurans were synthesized from their corresponding substituted l-allyl-2-allyloxybenzenes using ruthenium-mediated G and O-allyl isomerization followed by ring-closing metathesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.090
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 34.0h， 生成 2-allyloxy-1,4-dimethoxybenzene
  参考文献：
  名称：

  Synthetic Models Related to Methoxalen – CYP2A6 Interactions. Dimethoxybenzofuran Derivatives as Potent and Selective Inhibitors of CYP2A6

  摘要：

  The human CYP2A6 enzyme metabolizes several xenobiotics including nicotine, the addictive component in tobacco. Reduced activity of CYP2A6, either for genetic reasons or by administering inhibitors of CYP2A6, reduces tobacco smoking. The reported compound methoxalen had a potent inhibitory effect on activity of CYP2A6 with an IC50 value of 1.27 mu M. We selected methoxalen as a lead compound and prepared various dimethoxybenzofuran derivatives that have inhibitory effects on activity of human cytochrome P450 (CYP) 2A6. Synthetic benzofuran derivatives (3,6-dimethoxybenzofuran: IC50=1.92 mu M and 3,7-dimethoxybenzofuran: IC50=2.00 mu M) also exhibited comparable activities against CYP2A6 and were selective inhibitors of CYP2A6. These compounds can be used as lead compounds in the development of drugs for smoking reduction therapy.

  DOI：

  10.3987/com-13-12744

文献信息

• Synthesis of coumarins by ring-closing metathesis using Grubbs’ catalyst
  作者：Tuyen Nguyen Van、Silvia Debenedetti、Norbert De Kimpe

  DOI：10.1016/s0040-4039(03)00902-x

  日期：2003.5

  A novel generally applicable synthesis of coumarins from phenolic substrates utilizing ring-closing metathesis is described. This sequence involves O-allylation of phenols followed by ortho-Claisen rearrangement, subsequent based-induced isomerization affording 2-(1-propenyl)phenols, acylation with acryloyl chloride, and finally ring-closing metathesis (RCM) with Grubbs’ second generation catalyst

  描述了一种利用闭环易位从酚类底物合成香豆素的新的普遍适用的合成方法。该序列涉及苯酚的O-烯丙基化，然后进行邻-克莱森重排，随后进行基于碱的诱导异构化，得到2-（1-丙烯基）苯酚，与丙烯酰氯进行酰化，最后用Grubbs的第二代催化剂进行闭环复分解（RCM）。 。
• Ring-closing metathesis for the synthesis of benzo-fused bicyclic compounds
  作者：Willem A.L. van Otterlo、E.Lindani Ngidi、E.Mabel Coyanis、Charles B. de Koning

  DOI：10.1016/s0040-4039(02)02522-4

  日期：2003.1

  Ring-closing metathesis (RCM) was used to synthesise five 4H-chromenes, a naphthol and an indenol. These are the first examples of RCM applied to the synthesis of such benzo-fused bicyclic compounds.

  闭环复分解（RCM）用于合成五个4 H-色烯，萘酚和茚满醇。这些是应用于此类苯并稠合双环化合物合成的RCM的第一个实例。
• SYNTHESIS OF THE TRIMETHOXYPHENYLPROPENES
  作者：Alexander T. Shulgin

  DOI：10.1139/v65-478

  日期：1965.12.1

  not available

  不可用。
• Ring-closing metathesis for the synthesis of 2H- and 4H-chromenes
  作者：Willem A.L. van Otterlo、E. Lindani Ngidi、Samuel Kuzvidza、Garreth L. Morgans、Simon S. Moleele、Charles B. de Koning

  DOI：10.1016/j.tet.2005.08.020

  日期：2005.10

  Six 4H-chromenes were synthesized from substituted phenols using vinylstannylation and ring-closing metathesis (RCM) as key steps. In addition, a different approach involving amongst other steps, an aryl allyl isomerization and RCM afforded a set of seven 2H-chromenes from phenolic precursors. (c) 2005 Elsevier Ltd. All rights reserved.
• An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans
  作者：Willem A.L. van Otterlo、Garreth L. Morgans、Lee G. Madeley、Samuel Kuzvidza、Simon S. Moleele、Natalie Thornton、Charles B. de Koning

  DOI：10.1016/j.tet.2005.05.090

  日期：2005.8

  Twelve substituted benzofurans were synthesized from their corresponding substituted l-allyl-2-allyloxybenzenes using ruthenium-mediated G and O-allyl isomerization followed by ring-closing metathesis. (c) 2005 Elsevier Ltd. All rights reserved.