2-((4-fluorophenyl)ethynyl)phenol | 1142173-51-0

• 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-((4-fluorophenyl)ethynyl)phenol
• 英文别名: 2-[2-(4-fluorophenyl)ethynyl]phenol
• CAS: 1142173-51-0
• 化学式: C₁₄H₉FO
• 分子量: 212.223
• InChiKey: CRGHUPHQJTXAAR-UHFFFAOYSA-N

物化性质

• 熔点：
  111-112 °C
• 沸点：
  338.8±27.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((4-fluorophenyl)ethynyl)phenol 在 N-碘代丁二酰亚胺 、 三苯基膦 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.08h， 以92%的产率得到2-(4-fluorophenyl)-3-iodobenzofuran
  参考文献：
  名称：

  通过Ph 3 P催化的碘化环化反应合成3-碘吲哚和3-碘苯并[ b ]呋喃的简便方法

  摘要：

  各种3-碘吲哚和3-碘代苯并〔b被方便地从相应的2- alkynylanilines和2- alkynylphenols通过pH下制备]呋喃衍生物3在存在P-催化iodocyclization Ñ碘代丁二酰亚胺（NIS）。这个协议提供了一个快速访问3- iodoindoles和3-碘代苯并〔b〕呋喃在良好到温和的条件下具有优异的产率。

  DOI：

  10.1016/j.tet.2015.09.005
• 作为产物：
  描述：

  1-碘-2-(甲氧基甲氧基)苯 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 2-((4-fluorophenyl)ethynyl)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

• Iridium(<scp>i</scp>)-catalyzed hydration/esterification of 2-alkynylphenols and carboxylic acids
  作者：Linwei Zeng、Renjie Chen、Chen Zhang、Hujun Xie、Sunliang Cui

  DOI：10.1039/c9cc09984k

  日期：——

  An iridium(i)-catalyzed hydration/esterification of 2-alkynylphenols and carboxylic acids is described. Various 2-alkynylphenols and carboxylic acids could be used in this process to furnish aromatic ortho-acyloxyketones via a regio- and stereo-selective addition reaction followed by intramolecular rearrangement. This protocol features mild reaction conditions and broad substrate scope. Further transformations

  描述了铱（i）催化的2-炔基苯酚和羧酸的水合/酯化。各种2-炔基苯酚和羧酸可用于该过程中，通过区域和立体选择性加成反应，然后进行分子内重排，提供芳族邻-酰氧基酮。该方案具有温和的反应条件和广泛的底物范围。进行了进一步的转化以证明合成应用。
• Rhodium(III)-Catalyzed Cascade Cyclization/Electrophilic Amidation for the Synthesis of 3-Amidoindoles and 3-Amidofurans
  作者：Zhiyong Hu、Xiaofeng Tong、Guixia Liu

  DOI：10.1021/acs.orglett.6b00689

  日期：2016.5.6

  A rhodium(III)-catalyzed cascade cyclization/electrophilic amidation using N-pivaloyloxylamides as the electrophilic nitrogen source has been developed. This protocol provides an efficient route for the synthesis of 3-amidoindoles and 3-amidofurans under mild conditions with good functional group tolerance. The synthetic utility of this reaction has been demonstrated through the derivatization of the

  已经开发了使用N-新戊酰氧基叠氮化物作为亲电子氮源的铑（III）催化的级联环化/亲电子酰胺化。该方案为在温和条件下具有良好官能团耐受性的3-酰胺基吲哚和3-酰胺基呋喃的合成提供了一条有效途径。该反应的合成效用已经通过3-酰胺基吲哚的衍生化为几个杂环稠合的吲哚得到了证明。
• A Facile Construction of Bisheterocyclic Methane Scaffolds through <scp>Palladium‐Catalyzed</scp> Domino Cyclization
  作者：Hongbo Qi、Kaiming Han、Shufeng Chen

  DOI：10.1002/cjoc.202100242

  日期：2021.10

  A convenient palladium-catalyzed domino cyclization reaction for the construction of bis(benzofuranyl)methane scaffolds bearing an all-carbon quaternary center has been described. In the cascade process, one C(sp2)—O bond, two C(sp2)—C(sp3) bonds as well as two benzofuran rings are formed in a single synthetic sequence. The approach shows wide scope of substrates and good functional-group tolerance

  已经描述了一种方便的钯催化的多米诺环化反应，用于构建带有全碳四元中心的双（苯并呋喃基）甲烷支架。在级联过程中，一个C(sp 2 )-O 键、两个C(sp 2 )-C(sp 3 ) 键以及两个苯并呋喃环在单一合成序列中形成。该方法显示出广泛的底物和良好的官能团耐受性。此外，该方法成功地扩展到苯并呋喃基甲基色满衍生物的合成。
• 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。
• Access to 6H-naphtho[2,3-c]chromenes by a palladium-catalyzed reaction of 2-haloaryl allene with 2-alkynylphenol
  作者：Xiaolin Pan、Mo Chen、Liangqing Yao、Jie Wu

  DOI：10.1039/c4cc00374h

  日期：——

  A palladium-catalyzed reaction of 2-haloaryl allene with 2-alkynylphenol is described, leading to 6H-naphtho[2,3-c]chromenes in good to excellent yields. This transformation proceeds efficiently with excellent chemoselectivity and regioselectivity.

  描述了一种钯催化的反应，将2-卤代芳基炔丙烯与2-炔基苯酚反应，生成6H-萘[2,3-c]色烯，产率良好到优良。该转化反应高效进行，具有优异的化学选择性和区域选择性。