1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-yn-1-ol | 109600-56-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-yn-1-ol
• 英文别名: 2-(1-hydroxy-3-(4-methoxyphenyl)prop-2-ynyl)phenol；2-(1-hydroxy-3-(4-methoxyphenyl)prop-2-yn-1-yl)phenol；1-(o-hydroxyphenyl)-3-(4-methoxyphenyl)propargylic alcohol；1-(2-Hydroxy-phenyl)-3-(4-methoxy-phenyl)-prop-2-in-1-ol；1-(4-Methoxy-phenyl)-3-(2-hydroxy-phenyl)-1-propin-3-ol；2-[1-Hydroxy-3-(4-methoxyphenyl)prop-2-ynyl]phenol；2-[1-hydroxy-3-(4-methoxyphenyl)prop-2-ynyl]phenol
• CAS: 109600-56-8
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: ZMOBPSMSFXWVJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-yn-1-ol 在 manganese(IV) oxide 、 tricyclohexylphosphine-silver chloride 、 N,N-二异丙基乙胺 作用下， 以 水 、 甲苯 为溶剂， 反应 3.0h， 生成 (Z)-4'-methoxyaurone
  参考文献：
  名称：

  Water-Promoted, Silver–Phosphine Complex–Catalyzed Stereoselective Cyclization of 2-(1-Hydroxy-3-arylprop-2-ynyl)phenols Leading to a Highly Efficient Approach to Aurones

  摘要：

  Silver-phosphine complexes can be utilized as highly efficient catalysts for the cyclization of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols (1) to give product 2, key intermediates to synthesize aurones (4), with good yields and stereoselectivities in water-toluene mixed solvent. With fluoride as the counteranion, complete E- or Z-stereoselectivities were achieved at high temperature or room temperature, respectively. Furthermore, after removing water from the reaction mixtures, the toluene solution containing crude products 2 can be treated by MnO2 directly without further purification, to give aurones 4 in good yields.

  DOI：

  10.1080/00397911.2010.517613
• 作为产物：
  描述：

  苯酚 在 正丁基锂 、 氯仿 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 23.0h， 生成 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-yn-1-ol
  参考文献：
  名称：

  通过 LiOtBu/空气介导的氧化和邻羟基苯基炔丙基甲醇的区域选择性环化合成色酮

  摘要：

  以LiOtBu为介质，空气为氧化剂，开发了合成色酮衍生物的级联氧化环化反应。该反应在没有过渡金属的帮助下在温和条件下进行，以高产率和高区域选择性提供色酮。

  DOI：

  10.1002/ejoc.201201665

文献信息

• Divergence in Ynone Reactivity: Atypical Cyclization by 3,4-Difunctionalization versus Rare Bis(cyclization)
  作者：Benito Alcaide、Pedro Almendros、Carlos Lázaro-Milla、Patricia Delgado-Martínez

  DOI：10.1002/chem.201800630

  日期：2018.6.7

  yields in a totally selective manner. In this way, bis(triflyl)flavones, bis(triflyl)thioflavones, bis(triflyl)selenoflavones, (triflyl)benzothienopyrans, (triflyl)benzoselenophenopyrans, (triflyl)vinyl aurones, and (triflyl)pyranoindoles were constructed. Conceivable mechanistic pathways were suggested on the basis of the isolation of several intermediates and the results from control experiments

  可以通过Tf 2 C = CH 2激活功能化的炔酮，原位生成，形成两性离子物质。这些物种以分子内方式被数个亲核试剂捕获，以发散的方式产生两种主要类型的三苯甲酮。通过对反应温度的微调，以完全选择的方式以合理的收率获得了双（triflyl）-6元或（triflyl）-5元稠合杂环。以此方式，构建了双（三氟乙）黄酮，双（三氟乙）硫代黄酮，双（三氟乙）硒代黄酮，（三氟乙）苯并噻吩并吡喃，（三氟苯）苯并硒基苯并吡喃，（三氟乙）乙烯基金酮和（三氟乙）吡喃并吲哚。根据几种中间体的分离和对照实验的结果，提出了可能的机理途径。
• One-pot Synthesis of Aurones through Oxidation-cyclization Tandem Reaction Catalyzed by Copper Nanoparticles Catalyst
  作者：Min Yu、Guangxiang Liu、Chengyan Han、Li Zhu、Xiaoquan Yao

  DOI：10.2174/1570178614666171110150853

  日期：2017.12.11

  Aurones were synthesized through an oxidation-cyclization tandem reaction of 2-(1- hydroxyprop-2-ynyl)phenols catalyzed by copper nanoparticles (Cu NPs) with bipyridine as the ligand. In the reaction, oxygen worked as a green and mild oxidant to give the best results. Cu NPs were dually activated by bipyridine ligand and water, and showed highly efficient catalytic activities to the oxygen oxidation

  通过以联吡啶为配体的铜纳米粒子（Cu NPs）催化的2-（1-羟基丙-2-炔基）苯酚的氧化环化串联反应合成了金酮。在反应中，氧气起绿色和中度氧化剂的作用，以达到最佳效果。Cu NP被联吡啶配体和水双重激活，对氧的氧化和环化反应显示出高效的催化活性，从而生成金酮和类黄酮。
• Synthesis of Sulfonylated Heterocycles via Copper‐Catalyzed Heteroaromatization/Sulfonyl Transfer of Propargylic Alcohols
  作者：Xinyi Chen、Andrey Shatskiy、Jian‐Quan Liu、Markus D. Kärkäs、Xiang‐Shan Wang

  DOI：10.1002/asia.202001126

  日期：2021.1.4

  An unprecedented copper‐catalyzed heteroaromatization/sulfonyl transfer of propargylic alcohols with isocyanide has been developed. 3‐Sulfonyl benzofurans and indoles were produced under Cu(I) catalysis in good to high yields. The developed catalytic methodology provides controlled, modular, and facile access to sulfonyl benzoheterocycle scaffolds.

  已经开发了前所未有的铜催化的炔丙醇与异氰酸酯的杂芳烃化/磺酰基转移。在Cu（I）催化下以高到高收率生产3-磺酰基苯并呋喃和吲哚。先进的催化方法提供了对磺酰基苯并杂环支架的控制，模块化和便捷操作。
• 1,4-Conjugate addition/esterification of <i>ortho</i>-quinone methides in a multicomponent reaction
  作者：Renjie Chen、Yu Liu、Sunliang Cui

  DOI：10.1039/c8cc07328g

  日期：——

  A novel 1,4-conjugate addition/esterification of ortho-quinone methides in a multicomponent reaction has been developed. In this protocol, numerous carboxylic acids, ynamides and in situ generated ortho-quinone methides could assemble rapidly to constitute this process for the synthesis of functionalized 3,3-diarylpropanamides with sufficient structural diversity. Furthermore, the products could be

  的新的1,4-共轭加成/酯化邻-quinone的甲基化物中的多组分反应已经研制成功。在该方案中，许多羧酸，乙酰胺和原位生成的邻醌甲基化物可以迅速组装，从而构成用于合成具有足够结构多样性的官能化3,3-二芳基丙酰胺的过程。此外，可以将产物转化为一系列化合物。
• Cu(OAc)₂·H₂O-Promoted Tandem β-Alkynyl Elimination of α- or β-Hydroxy Propargylic Alcohols and Homocoupling of the Resulting Alkynyl Species
  作者：Xiangsheng Xu、Zhenyong Huang、Yanfeng Lu

  DOI：10.3184/174751913x13739011239995

  日期：2013.9

  α or β-hydroxy propargylic alcohols undergo tandem C(sp)–C(sp3) bond cleavage via β-alkynyl elimination and homo-coupling of the resulted alkynyl species in the presence of Cu(OAc)2·H2O to produce the corresponding hydroxycarbonyl compounds and 1,3-butadiynes.

  α 或 β-羟基炔丙醇在 Cu(OAc)2·H2O 存在下通过 β-炔基消除和所得炔基的均偶联发生串联 C(sp)–C(sp3) 键断裂，生成相应的羟基羰基化合物和 1,3-丁二炔。