(E)-ethyl 3-(2-hydroxy-3-methylphenyl)acrylate | 189574-84-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-ethyl 3-(2-hydroxy-3-methylphenyl)acrylate
• 英文别名: ethyl (E)-3-(2-hydroxy-3-methylphenyl)prop-2-enoate
• CAS: 189574-84-3
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: QRSSPZFPSXXFTO-BQYQJAHWSA-N

物化性质

• 沸点：
  330.4±27.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-(2-hydroxy-3-methylphenyl)acrylate 在 三丁基膦 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 ethyl (1S,9bS)-6-methyl-4-oxo-2,9b-dihydro-1H-cyclopenta[c]chromene-1-carboxylate
  参考文献：
  名称：

  Phosphine-Catalyzed Synthesis of Highly Functionalized Coumarins

  摘要：

  [GRAPHICS]2-Styrenyl allenoates are converted into cyclopentene-fused dihydrocoumarins through phosphine-catalyzed regio- and diastereoselective [3 + 2] cycloadditions. Remarkably, changing the solvent from THF to benzene promotes the conversion of the 2-(2-nitrostyrenyl) allenoate into a tricyclic nitronate through a previously undocumented mode of phosphine catalysis. This nitronate was subjected to efficient face-, regio-, and exo-selective 1,3-dipolar cycloadditions to provide tetracyclic coumarin derivatives.

  DOI：

  10.1021/ol071181d
• 作为产物：
  描述：

  2-甲基-1-(2'-四氢吡喃氧基)苯 在 正丁基锂 、 四甲基乙二胺 、 对甲苯磺酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 26.5h， 生成 (E)-ethyl 3-(2-hydroxy-3-methylphenyl)acrylate
  参考文献：
  名称：

  TETRAHYDROPYRANYLOXY-DIRECTEDorthoLITHIATION OF AROMATIC SYSTEMS. SYNTHESIS OFo-HYDROXYCINNAMATE ESTERS FROM PHENOLS

  摘要：

  DOI：

  10.1080/00304949709355199

文献信息

• Late‐Stage Direct <i>o</i> ‐Alkenylation of Phenols by Pd ^II ‐Catalyzed C−H Functionalization
  作者：Yandong Dou、Kenry、Jiang Liu、Jianze Jiang、Qing Zhu

  DOI：10.1002/chem.201900530

  日期：2019.5.17

  phenol as a directing group, high regioselectivity, good substrate scope, mild reaction conditions, and high efficiency. To the best of our knowledge, this is the first example of a regioselective C−H alkenylation of unprotected phenols utilizing phenolic hydroxyl group as a directing group. The alkenylation of unprotected tyrosine and intramolecular cyclization are also successfully carried out under

  通过Pd II催化的直接C-H官能化已开发出未保护的酚的o-烯基化。这项工作以酚基团为导向基团，并实现了酚的位点选择性C-H键官能化，从而在60°C时以中等至极好的收率获得了相应的产品。该反应的优点包括使用苯酚作为指导基团进行前所未有的CH官能化，区域选择性高，底物范围广，反应条件温和且效率高。据我们所知，这是利用酚羟基作为指导基团对未保护的酚进行区域选择性CH烯基化的第一个例子。未保护的酪氨酸的烯基化和分子内环化也可以在该催化体系下以高收率成功进行。此外，
• Visible-Light-Induced C(sp²)–C(sp³) Coupling Reaction for the Regioselective Synthesis of 3-Functionalized Coumarins
  作者：Ke Zhang、Li Qiao、Jianwei Xie、Zhenwei Lin、Hanjie Li、Ping Lu、Yanguang Wang

  DOI：10.1021/acs.joc.1c00848

  日期：2021.7.16

  A photocatalysis strategy for the regioselective synthesis of 3-functionalized coumarins is reported. With visible light irradiation, a direct and regioselective C(sp2)–C(sp3) coupling reaction of 3-(2-hydroxyphenyl)acrylates with ethers or thioethers occurs by using Ru(bpy)3Cl2·6H2O as a photocatalyst and TBHP as an oxidant. The cascade process involves alkenylation of the C(sp3)–H bond of ethers

  报道了一种用于区域选择性合成 3 官能化香豆素的光催化策略。在可见光照射下，3-(2-羟基苯基)丙烯酸酯与醚或硫醚发生直接和区域选择性的C(sp 2 )–C(sp 3 )偶联反应，使用Ru(bpy) 3 Cl 2 ·6H 2 O作为光催化剂和TBHP作为氧化剂。级联过程涉及 C(sp 3)-H 键的醚和内酯化，提供 3-烷基化香豆素作为最终产品。该方法的特点是底物范围广、反应条件温和、操作简单。3-烷基化香豆素的合成可以通过一锅法实现，从市售的水杨醛开始。
• Ruthenium(II)-Catalyzed CH Alkenylations of Phenols with Removable Directing Groups
  作者：Wenbo Ma、Lutz Ackermann

  DOI：10.1002/chem.201301988

  日期：2013.10.4

  Cationic ruthenium(II) complexes enabled oxidative alkenylations of phenols bearing easily cleavable directing groups. The optimized catalytic system allowed twofold CH bond activations with excellent chemo‐, site‐, and diastereoselectivities. The double CH functionalization process proceeded efficiently in an aerobic fashion under an atmosphere of ambient air. Detailed mechanistic studies were performed

  阳离子钌（II）配合物可以使带有易于裂解的导向基团的酚进行氧化性烯基化反应。优化的催化系统可实现双重的CH键活化，具有出色的化学，位点和非对映选择性。在环境空气气氛下，双重CH功能化过程以有氧方式有效进行。进行并提供用于初始可逆Ç强烈支持的详细机理研究通过的六元ruthenacycles作为关键中间体的形成H键活化。
• Phosphine-Catalyzed Synthesis of Highly Functionalized Coumarins
  作者：Christopher E. Henry、Ohyun Kwon

  DOI：10.1021/ol071181d

  日期：2007.8.1

  [GRAPHICS]2-Styrenyl allenoates are converted into cyclopentene-fused dihydrocoumarins through phosphine-catalyzed regio- and diastereoselective [3 + 2] cycloadditions. Remarkably, changing the solvent from THF to benzene promotes the conversion of the 2-(2-nitrostyrenyl) allenoate into a tricyclic nitronate through a previously undocumented mode of phosphine catalysis. This nitronate was subjected to efficient face-, regio-, and exo-selective 1,3-dipolar cycloadditions to provide tetracyclic coumarin derivatives.
• TETRAHYDROPYRANYLOXY-DIRECTED<i>ortho</i>LITHIATION OF AROMATIC SYSTEMS. SYNTHESIS OF<i>o</i>-HYDROXYCINNAMATE ESTERS FROM PHENOLS
  作者：Richard A. Bunce、Joel D. Moore

  DOI：10.1080/00304949709355199

  日期：1997.6