4-(tert-butyl)-2-(phenylethynyl)phenol | 122778-94-3

• 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: 4-(tert-butyl)-2-(phenylethynyl)phenol
• 英文别名: 4-Tert-butyl-2-(2-phenylethynyl)phenol
• CAS: 122778-94-3
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: WGVBXAQUISAEJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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-(tert-butyl)-2-(phenylethynyl)phenol 在 甲烷磺酸 、 C₂₂H₂₆AuCl₂N₃O₂S 作用下， 以 氯仿 为溶剂， 以96 %的产率得到苯并呋喃,5-(1,1-二甲基乙基)-2-苯基-
  参考文献：
  名称：

  原位布朗斯台德酸活化环金属化 N-杂环卡宾-Au(III)-磺酰胺配合物作为苯并呋喃合成中炔烃活化的预催化剂

  摘要：

  [(NHC)Au(N)Cl 2 ]类型的环金属化N-杂环卡宾(NHC)-NTs-AuCl 2配合物是一种稳定的预催化剂，很容易被酸(HX)原位激活，产生阳离子[(NHC) AuCl 2 ]X催化。通过 K 2 CO 3处理以及添加化学计量的布朗斯台德酸，“乙基和丙基甲苯磺酰胺臂”束缚的 NHC-Au(III)Cl 3配合物可以顺利转化为环金属化 (-HCl) 类似物(HX)，可进一步转化为携带各种抗衡阴离子的[NHC-Au(III)Cl 2 ]X (X = CCl 3 CO 2 – , CF 3 CO 2 – , MsO – , TsO – , BF 4 – , TfO –、Tf 2 N – )。我们使用 2-炔基苯酚环异构化为苯并呋喃作为探针反应，研究了这一催化概念。在环境条件下，在CHCl 3中，使用等摩尔1mol%负载的Mes-NHC-丙基-NTs-AuCl 2预催化剂和MsOH作为

  DOI：

  10.1021/acs.organomet.3c00520
• 作为产物：
  描述：

  C₂₀H₂₂O₂ 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 4-(tert-butyl)-2-(phenylethynyl)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

• 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。
• Synthese und Eigenschaften von<i>o</i>-hydroxyphenyl- und<i>o</i>-acetylaminophenyl-substituierten Cyclopropenonen. Eine neuartige thermische Umwandlung funktionalisierter Diarylcyclopropenone
  作者：Theophil Eicher、Volker Schneider

  DOI：10.1055/s-1989-27255

  日期：——

  Synthesis and Properties of o-Hydroxyphenyl- and o-Acetylaminophenyl-Substituted Cyclopropenones. A Novel Thermal Transformation of Functionalized Cyclopropenones The ortho-functionalized arylphenylcyclopropenones 3 are prepared via the West method and their spectroscopic and chemical properties are reported. The cyclopropenones 3 undergo thermal transformation to give heterocycles 7, 8, 12, photochemically they are decarbonylated to give alkynes 9 as main products. The structures of the heterocycles 7, 8, 12 are proven by means of spectroscopic data and by independent synthesis. A mechanism for this novel thermal cyclopropenone transformation is discussed.

  o-羟基苯基和o-乙酰氨基苯基取代的环丙烯酮的合成及性质。功能化环丙烯酮的新型热转化。通过West方法合成了o-功能化芳香环丙烯酮3，并报道了其光谱及化学性质。环丙烯酮3经过热转化生成杂环化合物7、8和12，经过光化学反应则脱羧基生成炔烃9为主要产物。这些杂环化合物7、8和12的结构通过光谱数据和独立合成得到了证实。讨论了这一新型热环丙烯酮转化的机制。
• Domino rhodium(I)-catalysed reactions for the efficient synthesis of substituted benzofurans and indoles
  作者：Alistair Boyer、Naohiro Isono、Sebastian Lackner、Mark Lautens

  DOI：10.1016/j.tet.2010.05.106

  日期：2010.8

  Rhodium(I) catalysts promote the transformation of o-alkynyl phenols and anilines to the corresponding benzo[b]furans and indoles. The reaction is postulated to proceed via a transient 3-rhodium heterocycle intermediate, which can be trapped with suitable electrophiles to give poly-substituted heterocycles. In the case of mono-substituted electron-withdrawn electrophiles, excellent yield and selectivity

  铑（I）催化剂促进邻炔基苯酚和苯胺转化为相应的苯并[ b ]呋喃和吲哚。假定该反应通过过渡的3-铑杂环中间体进行，该中间体可以用合适的亲电试剂捕获以得到多取代的杂环。在单取代的吸电子亲电体的情况下，与Heck-Mizoroki反应相比，可以获得优异的收率和选择性。在2-炔基吡啶亲电试剂的情况下，形成新的2-（苯并呋喃-3-基）乙烯基吡啶。
• 3,3′-Bis(arylbenzofurans) via a Gold-Catalyzed Domino Process
  作者：Hermann Wegner、Mathieu Auzias、Markus Neuburger

  DOI：10.1055/s-0030-1258566

  日期：2010.10

  A new heterogeneous gold-catalyzed system for the domino cyclization oxidative coupling of 2-alkynyl phenols for the formation of 3,3`-bisbenzofurans was developed. The substrate and the catalyst scope as well as the reaction conditions were investigated and optimized. This method provides access to this novel structural theme in two steps starting from commercially available chemicals. The molecular

  开发了一种新的非均相金催化体系，用于 2-炔基酚的多米诺环化氧化偶联形成 3,3'-双苯并呋喃。对底物和催化剂的适用范围以及反应条件进行了研究和优化。该方法从市售化学品开始，分两步提供了对这种新型结构主题的访问。3,3`-双苯并呋喃的分子结构由单晶X射线分析证实。
• 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。