4-methyl-2-(p-tolylethynyl)phenol | 1338699-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-methyl-2-(p-tolylethynyl)phenol
• 英文别名: 4-Methyl-2-[2-(4-methylphenyl)ethynyl]phenol；4-methyl-2-[2-(4-methylphenyl)ethynyl]phenol
• CAS: 1338699-35-6
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: CGAMZSMJQVAASN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(p-tolylethynyl)phenol 在 叔丁基过氧化氢 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 22.0h， 生成 (E)-6-methyl-4-(4-methylbenzylidene)-3-((phenylsulfonyl)methyl)chromane
  参考文献：
  名称：

  含氧的1,7-烯炔烃的无金属自由基环化：（E）-3-（（芳基磺酰基）甲基）-4-取代的亚芳基亚甲基衍生物的构型选择性合成

  摘要：

  通过含氧的1,7-烯炔与硫代磺酸盐的金属自由基环合反应，开发了一种新的策略来合成（E）-3-（（芳基磺酰基）甲基）-4-取代的亚苄基亚甲基衍生物。该反应显示出宽的底物范围，宽的官能团耐受性和中等至优异的产率。此外，硫代磺酸盐被很好地驱动以实现衍生自脂族炔烃的oxo-1,7-烯炔的双官能化反应。另外，产物的（E）-构型由1，7-烯炔的结构高度控制。

  DOI：

  10.1021/acs.orglett.0c03946
• 作为产物：
  描述：

  2-碘-4-甲基苯酚 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-methyl-2-(p-tolylethynyl)phenol
  参考文献：
  名称：

  Highly efficient heterogeneous synthesis of benzofurans under aqueous condition

  摘要：

  Highly efficient organic reactions in water are important for designing environmental-friendly and low cost synthetic processes. Herein, we demonstrate an intermediate-in-water strategy for the heterogeneous synthesis of benzofurans in aqueous media. The cyclization reaction of 2-(phenylethynyl)phenol to 2-phenylbenzofuran cannot proceed in pure water. However, this reaction can be efficiently promoted by the formation of sparingly soluble intermediate in the presence of alkaline. Quantitative conversion of a variety of substrates to benzofuran derivatives has been achieved in the absence of noble metal catalyst. Other remarkable features including easy-isolation and purification of product, along with wide range of functional group tolerance render the methodology promising in the realm of green-synthesis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.005

文献信息

• Zinc-catalyzed regioselective C–P coupling of <i>p</i>-quinol ethers with secondary phosphine oxides to afford 2-phosphinylphenols
  作者：Ming Zhang、Xiaoyu Jia、Haowei Zhu、Xutong Fang、Chenyi Ji、Sizhuo Zhao、Li-Biao Han、Ruwei Shen

  DOI：10.1039/c9ob00129h

  日期：——

  regioselective C–P cross coupling reaction of p-quinol ethers with secondary phosphine oxides is reported. The reaction provides a facile alternative method for the synthesis of 2-phosphinylphenols in good to high yields. Mechanistically, zinc triflate may serve as an oxophilic σ-Lewis acid to activate the C–O bond in p-quinol ether first. Then the regioselective attack of the phosphorus nucleophile at the α-carbon

  据报道，三氟甲磺酸锌催化对苯二酚醚与仲氧化膦的高度区域选择性C–P交叉偶联反应。该反应为以高产率到高产率合成2-次膦酰基苯酚提供了一种简便的替代方法。机械地，三氟甲磺酸锌可以用作亲氧性σ的路易斯酸来激活在C-O键p -quinol醚第一。然后，磷亲核体在α-碳位置发生区域选择性攻击，形成C–P键并生成产物。另外，在锌催化剂的存在下，α-炔基取代的对苯二酚醚也以相同的反应模式与仲膦氧化物反应，得到6-炔基2-膦基苯酚。
• A palladium-catalyzed tandem reaction of 2-(2-bromobenzylidene)cyclobutanone with 2-alkynylphenol
  作者：Xiaolin Pan、Yong Luo、Hong-Guang Xia、Jie Wu

  DOI：10.1039/c5cc07360j

  日期：——

  An efficient approach for the generation of benzo[b]naphtho[2,3-d]oxocin-6-ones through a palladium-catalyzed tandem reaction of 2-alkynylphenol with 2-(2-bromobenzylidene)cyclobutanone is described. This tandem process afforded the fused polycycles easily, with the formation of three bonds with high efficiency and excellent selectivity.

  通过钯催化的2-炔基苯酚与2-(2-溴苯基亚甲基)环丁酮的串联反应，描述了一种高效的制备苯并[b]萘并[2,3-d]氧喹啉-6-酮的方法。这种串联过程容易地形成融合多环化合物，高效地形成三个键，并具有优异的选择性。
• Transition-metal-free base catalyzed intramolecular cyclization of 2-ynylphenols for efficient and facile synthesis of 2-substituted benzo[<i>b</i>]furans
  作者：Yong Liu、Tao Lu、Wei-Fang Tang、Jian Gao

  DOI：10.1039/c8ra03882a

  日期：——

  A transition-metal-free base catalyzed intramolecular cyclization of 2-ynylphenols was developed for the facile synthesis of 2-substituted benzo[b]furans. Various 2-aryl and 2-alkyl substituted benzo[b]furans can be obtained with good to excellent yields using readily available Cs2CO3 as the catalyst under mild reaction conditions. The broad substrates scope and the typical maintenance of vigorous

  开发了一种无过渡金属碱催化的 2-炔基酚分子内环化，用于简便合成 2-取代的苯并[ b ]呋喃。使用容易获得的 Cs 2 CO 3作为催化剂，在温和的反应条件下，可以以良好至优异的收率获得各种 2-芳基和 2-烷基取代的苯并[ b ]呋喃。广泛的底物范围和克级高效效率的典型维持使该协议成为合成 2-取代苯并[ b ]呋喃衍生物的潜在实用方法。
• A New Insight into Palladium-Catalyzed Reaction of 2-Alkynylphenol with Carbon Monoxide
  作者：Yong Luo、Jie Wu

  DOI：10.1021/ol202478u

  日期：2011.11.4

  A novel and efficient pathway for the generation of 3-(benzofuran-3-ylmethylene)benzofuran-2(3H)-ones via a palladium-catalyzed carbonylative reaction of 2-alkynylphenol with carbon monoxide is described. The reaction proceeds through a double insertion of triple bonds during the reaction process. The products are obtained in good yields with high selectivity. A one-pot synthesis starting from 2-iodophenol

  描述了通过钯催化的2-炔基苯酚与一氧化碳的羰基化反应生成3-（苯并呋喃-3-基亚甲基）苯并呋喃-2（3 H）-的新颖而有效的途径。反应在反应过程中通过三键的两次插入而进行。以高收率和高选择性获得产物。还提出了一种从2-碘苯酚和炔烃开始的一锅法合成法。
• Direct Assembly of 3,4-Difunctionalized Benzofurans and Polycyclic Benzofurans by Phenol Dearomatization and Palladium-Catalyzed Domino Reaction
  作者：Zhaomeng Han、Liang Zhang、Zhiming Li、Renhua Fan

  DOI：10.1002/anie.201404155

  日期：2014.6.23

  A method to directly convert 2‐alkynylphenols to 3,4‐difunctionalized benzofurans and polycyclic benzofurans was developed. This protocol involves a hypervalent‐iodine‐mediated oxidative dearomatization to break the aromaticity of 2‐alkynylphenols, and a palladium‐catalyzed domino reaction to install two functional groups at the C3 and the C4 positions and restore the aromaticity of benzofurans.

  提出了一种将2-炔基苯酚直接转化为3,4-双官能化苯并呋喃和多环苯并呋喃的方法。该方案涉及高价碘介导的氧化脱芳香化作用，以破坏2-炔基苯酚的芳香性，以及钯催化的多米诺反应，以在C3和C4位置安装两个官能团并恢复苯并呋喃的芳香性。