4-chloro-2-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol | 1262020-27-8

• 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: 4-chloro-2-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol
• 英文别名: 4-Chloro-2-(1-hydroxy-3-phenylprop-2-ynyl)phenol；4-chloro-2-(1-hydroxy-3-phenylprop-2-ynyl)phenol
• CAS: 1262020-27-8
• 化学式: C₁₅H₁₁ClO₂
• 分子量: 258.704
• InChiKey: GADQVYZJQYJKEG-UHFFFAOYSA-N

物化性质

• 沸点：
  441.5±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-2-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol 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 2.0h， 生成 (Z)-2-benzylidene-5-chlorobenzofuran-3(2H)-one
  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：

  对氯苯酚 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 4-chloro-2-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol
  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

• Lewis Acid Catalyzed Tandem 1,4-Conjugate Addition/Cyclization of in Situ Generated Alkynyl <i>o</i>-Quinone Methides and Electron-Rich Phenols: Synthesis of Dioxabicyclo[3.3.1]nonane Skeletons
  作者：Ji-Yuan Du、Yan-Hua Ma、Fan-Xiao Meng、Bao-Li Chen、Shao-Liang Zhang、Qian-Li Li、Shu-Wen Gong、Da-Qi Wang、Chun-Lin Ma

  DOI：10.1021/acs.orglett.8b01862

  日期：2018.7.20

  A versatile Lewis acid catalyzed tandem cyclization of in situ generated alkynyl o-quinone methides (o-AQMs) with electron-rich phenols has been developed on the basis of the mode involving an intermolecular 1,4-conjugate addition/6-endo cyclization/1,3-aryl shift/intramolecular 1,4-conjugate addition cascade. This reaction provides a new method for expeditious assembly of synthetically and biologically

  基于涉及分子间1,4-共轭加成/ 6 /内-环化/的分子式的方法，开发了一种通用的路易斯酸催化串联环化与富电子酚的原位炔基邻-醌甲基化物（o -AQMs）。 1,3-芳基转移/分子内1,4-共轭加成级联。该反应提供了一种新的方法，用于快速合成和生物学上有趣的四环桥联的二氧杂双环[3.3.1]壬烷骨架，其特征是桥头氧杂-四元立体中心拥塞。
• Ligand-Promoted, Copper Nanoparticles Catalyzed Oxidation of Propargylic Alcohols with TBHP or Air as Oxidant
  作者：Xiaoquan Yao、Chengyan Han、Min Yu、Weijiang Sun

  DOI：10.1055/s-0030-1261227

  日期：2011.10

  A highly efficient oxidation of propargylic alcohols to ynones was catalyzed by copper nanoparticles (Cu Nps) with TBHP as an oxidant at room temperature. With bipyridine as the ligand, the reaction was accelerated significantly and led in good to excellent yields to a variety of propargylic alcohols. Furthermore, with Cu Nps as the catalyst, molecular oxygen in air could be utilized as oxidant effectively

  在室温下，以TBHP为氧化剂的铜纳米颗粒（Cu Nps）催化了炔丙醇高效氧化为炔酮。以联吡啶为配体，反应显着加速，并导致各种炔丙基醇的收率良好至优异。此外，以Cu Nps为催化剂，在存在bpy配体的情况下，空气中的分子氧可以有效地用作氧化剂。 炔丙醇-氧化-炔酮-铜纳米颗粒-配体效应
• Metal-Free One-Pot Synthesis of 3-Phosphinoylbenzofurans via Phospha-Michael Addition/Cyclization of H-Phosphine Oxides and <i>in Situ</i> Generated <i>ortho-</i>Quinone Methides
  作者：Ji-Yuan Du、Yan-Hua Ma、Rui-Qing Yuan、Nana Xin、Shao-Zhen Nie、Chun-Lin Ma、Chen-Zhong Li、Chang-Qiu Zhao

  DOI：10.1021/acs.orglett.7b03863

  日期：2018.1.19

  A novel metal-free one-pot protocol for the effective and efficient synthesis of 3-phosphinoylbenzofurans via a phospha-Michael addition/cyclization of H-phosphine oxides and in situ generated ortho-quinone methides is described. Based on the expeditious construction of C(sp2)–P bonds, asymmetric synthesis of optically pure 3-phosphinoylbenzofurans containing chiral P-stereogenic center has also been

  描述了一种新颖的无金属一锅方案，该方案通过H-膦氧化物的磷化-迈克尔加成/环化作用和原位生成的邻醌甲基化物来有效和高效地合成3-膦酰基苯并呋喃。基于C（sp 2）-P键的快速构建，还通过使用手性R P -（-）-薄荷基苯基膦氧化物探索了含手性P-立体异构中心的光学纯3-膦酰基苯并呋喃的不对称合成。
• 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。