2-ethenyl-6-hydroxy-4-methoxybenzoic acid

• 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-ethenyl-6-hydroxy-4-methoxybenzoic acid
• 英文别名: 2-hydroxy-4-methoxy-6-vinylbenzoic acid
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: GVZHTMDXCSRCSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-ethenyl-6-hydroxy-4-methoxybenzoic acid 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.5h， 生成 (3aS,7S,17S,17aS,14E)-10-hydroxy-12-methoxy-17-(methoxymethoxy)-2,2,7-trimethyl-4,5,6,7,17,17a-hexahydro-3aH-benzo[c][1,3]dioxolo[4,5-i][1]oxacyclotetradecin-9(16H)-one
  参考文献：
  名称：

  Stereoselective total synthesis of paecilomycin E

  摘要：

  First total synthesis of recently isolated resorcylic acid lactone paecilomycin E has been accomplished. The key reactions include olefin metathesis, Mitsunobu reaction, Stille coupling and regioselective allylation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.137
• 作为产物：
  描述：

  三氟甲烷磺酸7-甲氧基-2,2-二甲基-4-氧代-4H-1,3-苯并二氧杂环己-5-基酯 在 四(三苯基膦)钯 、 lithium hydroxide monohydrate 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 2-ethenyl-6-hydroxy-4-methoxybenzoic acid
  参考文献：
  名称：

  首次选择性立体合成青霉素G

  摘要：

  间苯二酸内酯，paecilomycin G（1）的立体选择性全合成已完成。涉及的关键步骤是Corey-Fuchs反应，Sharpless不对称二羟基化，Jacobsen水解动力学拆分，Stille偶联，Mitsunobu反应和闭环复分解（RCM）反应。

  DOI：

  10.1016/j.tetlet.2016.05.046

文献信息

• Asymmetric Total Syntheses of Cochliomycin A and Zeaenol
  作者：Nandan Jana、Samik Nanda

  DOI：10.1002/ejoc.201200241

  日期：2012.8

  The first asymmetric total syntheses of two resorcylic acid lactones (RALs) – cochliomycin A and zeaenol – have been achieved in a divergent way. The main highlight of our strategy involves successful application of stereoselecive Keck allylation and Julia–Kocienski olefination to access an advanced intermediate, by starting from L-tartaric acid as a chiral pool compound. This intermediate is coupled

  两种间苯二酸内酯（RALs）——cochliomycin A 和玉米烯醇——的第一个不对称全合成已经以不同的方式实现。我们策略的主要亮点包括成功应用立体选择性 Keck 烯丙基化和 Julia-Kocienski 烯化，通过从 L-酒石酸作为手性池化合物开始获得高级中间体。该中间体与三取代的苯甲酸偶联，为两个目标分子提供共同的 RCM 前体。后期的闭环复分解，然后是官能团操作，以有效的方式产生目标分子。
• Carbohydrate-Based Studies Toward the Synthesis of Hamigeromycin E: A Stereoselective Total Synthesis of an Isomer of Zeaenol
  作者：Gannerla Saidachary、Bhimapaka China Raju

  DOI：10.1002/hlca.201500267

  日期：2016.6

  A stereoselective synthesis of 14‐membered macrolide hamigeromycin E (6) has been studied by employing ortho‐lithiated formylation, Barbier allylation, Julia–Kocienski olefination, Mitsunobu esterification, and ring‐closing metathesis (RCM) reactions. The final RCM reaction did not provide the target molecule. This study has prompted us to synthesize a stereoisomer of zeaenol and accomplish the total

  通过采用邻位平板化甲酰化，Barbier烯丙基化，Julia - Kocienski烯烃化，Mitsunobu酯化和闭环复分解（RCM）反应，研究了14元大环内酯类金霉素E（6）的立体选择性合成。最终的RCM反应未提供目标分子。这项研究促使我们合成了玉米烯醇的立体异构体，并通过上述方案完成了全合成。
• First stereoselective total synthesis of paecilomycin G
  作者：Sheshurao Bujaranipalli、Saibal Das

  DOI：10.1016/j.tetlet.2016.05.046

  日期：2016.6

  The stereoselective total synthesis of resorcylic acid lactone, paecilomycin G (1) has been accomplished. The key steps involved are the Corey–Fuchs reaction, Sharpless asymmetric dihydroxylation, Jacobsen hydrolytic kinetic resolution, Stille coupling, Mitsunobu reaction, and Ring-closing metathesis (RCM) reaction.

  间苯二酸内酯，paecilomycin G（1）的立体选择性全合成已完成。涉及的关键步骤是Corey-Fuchs反应，Sharpless不对称二羟基化，Jacobsen水解动力学拆分，Stille偶联，Mitsunobu反应和闭环复分解（RCM）反应。
• Asymmetric total synthesis of 5′-epi-paecilomycin-F
  作者：Nandan Jana、Samik Nanda

  DOI：10.1016/j.tetasy.2012.05.017

  日期：2012.5

  The asymmetric total synthesis of one of the stereoisomers of the naturally occurring 14-membered ring macrolide paecilomycin-F (5'-epi) has been reported in this article. The main highlight of the synthetic strategy involves the successful application of a ring closing metathesis (RCM) reaction at a late stage. Asymmetric Keck allylation, Sharpless asymmetric dihydroxylation, and Mitsunobu esterification have also been used successfully for the total synthesis of 5'-epi-paecilomycin-F. (C) 2012 Elsevier Ltd. All rights reserved.
• Fast and efficient synthesis of the complete LL-Z1640-2 framework
  作者：Neil Henry、Murray N. Robertson、Rodolfo Marquez

  DOI：10.1016/j.tetlet.2007.06.151

  日期：2007.8

  The convergent synthesis of the complete LL-Z1640-2 framework has been completed. This fast and efficient approach provides flexible access into the resorcyclic lactones. (c) 2007 Elsevier Ltd. All rights reserved.