2-allyl-3-benzyloxy-4-methoxyphenol | 501368-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-allyl-3-benzyloxy-4-methoxyphenol
• 英文别名: 4-Methoxy-3-phenylmethoxy-2-prop-2-enylphenol
• CAS: 501368-17-8
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: MHHCAKUTGVWMFP-UHFFFAOYSA-N

物化性质

• 沸点：
  414.7±40.0 °C(predicted)
• 密度：
  1.121±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-allyl-3-benzyloxy-4-methoxyphenol 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到(E)-3-(benzyloxy)-4-methoxy-2-(prop-1-enyl)phenol
  参考文献：
  名称：

  Total synthesis of pulverolide: revision of its structure

  摘要：

  A flexible and practical strategy toward the synthesis of rare 2H-furo[3,2-b]benzopyran-2-one skeleton has been developed. With a microwave-assisted cyclization-dehydration as the key transformation, the first total synthesis of pulverolide has been completed in 10 steps with 9% overall yield, leading to the revision of its proposed structure. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.044
• 作为产物：
  描述：

  2-allyl-3-(benzyloxy)-4-methoxybenzaldehyde 在 碳酸氢钠 、 间氯过氧苯甲酸 、 甲醇 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以82%的产率得到2-allyl-3-benzyloxy-4-methoxyphenol
  参考文献：
  名称：

  Total synthesis of pulverolide: revision of its structure

  摘要：

  A flexible and practical strategy toward the synthesis of rare 2H-furo[3,2-b]benzopyran-2-one skeleton has been developed. With a microwave-assisted cyclization-dehydration as the key transformation, the first total synthesis of pulverolide has been completed in 10 steps with 9% overall yield, leading to the revision of its proposed structure. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.044

文献信息

• Synthesis of Benzofurans from Isovanillin via C-Propenylation-O-Vinylation and Ring-closing Metathesis
  作者：Eng-Chi Wang、Tzu-Wei Tsai、Keng-Shiang Huang、Sie-Rong Li、You-Feng Wang、Yu-Li Lin、Yung-Hua Chen

  DOI：10.3987/com-04-10074

  日期：——

  2-Allyl-3-alkoxy-4-methoxyphenol, prepared from isovanillin via the Claisen rearrangement, O-alkylation and Baeyer-Villiger oxidation, were chloroethylated by two-phase reaction to furnish 1-allyl-3-alkoxy-(2-chloroethoxy)-4-methoxy- benzenes. The given compounds were treated with potassium tert-butoxide to undergo the isomerization of O-allyl group and dehydrochlorination of 2-chloroethoxy group to efficiently

  合成了衍生自异香草醛的取代苯并呋喃。2-Allyl-3-alkoxy-4-methoxyphenol 由异香草醛通过 Claisen 重排、O-烷基化和 Baeyer-Villiger 氧化制备，通过两相反应氯乙基化得到 1-allyl-3-alkoxy-(2-chloroethoxy) )-4-甲氧基苯。用叔丁醇钾处理给定的化合物，使 O-烯丙基异构化和 2-氯乙氧基脱氯化氢，从而有效地构建具有 C-丙烯基-O-乙烯基官能团的前体，用于闭环复分解 (RCM)一锅。然后，然后对前体进行 RCM，以分别以良好的总产率提供 4,5-O-双官能化苯并呋喃。
• A New Synthesis of Substituted 2,5-Dihydrobenzo[b]oxepines
  作者：Eng-Chi Wang、Ming-Kun Hsu、Yu-Li Lin、Keng-Shiang Huang

  DOI：10.3987/com-02-9545

  日期：——

  Based on Claisen rearrangement, Baeyer-Villiger oxidation, and ring-closing metathesis (RCM), a series of substituted 2,5-dihydrobenzo[b]oxepines were synthesized from isovanillin in good over-all yields. Other appropriate substituted 2,5-dihydrobenzo[b]oxepines prepared from corresponding phenol derivatives were also described.
• Total synthesis of pulverolide: revision of its structure
  作者：Wanqiu Yang、Jikai Liu、Hongbin Zhang

  DOI：10.1016/j.tetlet.2010.07.044

  日期：2010.9

  A flexible and practical strategy toward the synthesis of rare 2H-furo[3,2-b]benzopyran-2-one skeleton has been developed. With a microwave-assisted cyclization-dehydration as the key transformation, the first total synthesis of pulverolide has been completed in 10 steps with 9% overall yield, leading to the revision of its proposed structure. (C) 2010 Elsevier Ltd. All rights reserved.