2-((4-(trifluoromethyl)phenyl)ethynyl)phenol | 859510-32-0

• 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-(trifluoromethyl)phenyl)ethynyl)phenol
• 英文别名: 2-[4-(Trifluoromethyl)phenylethynyl]phenol；2-[2-[4-(trifluoromethyl)phenyl]ethynyl]phenol
• CAS: 859510-32-0
• 化学式: C₁₅H₉F₃O
• 分子量: 262.231
• InChiKey: YJMRATWHAGTVMT-UHFFFAOYSA-N

物化性质

• 沸点：
  343.9±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((4-(trifluoromethyl)phenyl)ethynyl)phenol 在 三乙烯二胺 、 三苯基膦双(三氟甲磺酰亚胺)金 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 10.0h， 生成 methyl (2SR,3SR)-2-butoxy-4-(4-(trifluoromethyl)phenyl)-2,3-dihydrobenzo[b]oxepine-3-carboxylate
  参考文献：
  名称：

  Gold-Catalyzed Cyclizations of (o-Alkynyl)phenoxyacrylates with External Nucleophiles: Regio- and Stereoselective Synthesis of Functionalized Benzo[b]oxepines

  摘要：

  A catalytic approach to benzo[b]oxepines with high stereoselectivity by Au-catalyzed cyclization of (o-alkynyl)phenoxyacrylates with various nucleophiles under mild reaction conditions has been developed. Notably, the use of vinyl ether instead of alcohol could afford the same benzoxepines. The reaction may proceed by Au-catalyzed oligomerization of vinyl ether to release the alcohol, which then reacts with (o-alkynyl)phenoxyacrylates to furnish the benzoxepines.

  DOI：

  10.1021/ol302252h
• 作为产物：
  描述：

  1-乙酰氧基-2-碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 肼 作用下， 生成 2-((4-(trifluoromethyl)phenyl)ethynyl)phenol
  参考文献：
  名称：

  Novel Pd^II-Mediated Cascade Carboxylative Annulation to Construct Benzo[b]furan-3-carboxylic Acids

  摘要：

  Benzo[b]furan-3-carboxylic acid (2) was generated from 1 by forming three new bonds in one step via a Pd-II-mediated cascade carboxylative annulation. The proposed mechanism was supported by the observation of an unusual acetylation of 1 as a side reaction together with an O-18-labeling study.

  DOI：

  10.1021/ol050876g

文献信息

• Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes
  作者：Hao Liang、Xiaobo He、Yaqi Zhang、Bin Chen、Jia-sheng Ouyang、Yongsu Li、Bendu Pan、Chitreddy V. Subba Reddy、Wesley Ting Kwok Chan、Liqin Qiu

  DOI：10.1039/d0cc04373g

  日期：——

  The copper(II)-catalyzed (4+1) cyclizations and copper(I)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionalized dimethyl (E)-3-benzylideneindoline-2,2-dicarboxylates and methyl 5-(2-hydroxyphenyl)-2-methoxy-4-phenylfuran-3-carboxylates were conveniently prepared

  通过使用高效，安全的碘鎓碘化物代替传统的重氮化合物，成功开发了铜（II）催化的（4 + 1）环化反应和铜（I）催化的碘化碘化物和炔烃的环加成反应。方便地以中等至优异的产率制备高度官能化的二甲基（E）-3-亚苄基吲哚啉-2，2-二羧酸酯和5-（2-羟基苯基）-2-甲氧基-4-苯基呋喃-3-羧酸甲酯。还讨论了可能的反应机理。
• Enantioselective intramolecular cyclization of alkynyl esters catalyzed by a chiral Br<scp>ø</scp>nsted base
  作者：Azusa Kondoh、Hoa Thi Quynh Tran、Kyoko Kimura、Masahiro Terada

  DOI：10.1039/c6cc01690a

  日期：——

  An enantioselective intramolecular cyclization reaction of alkynyl esters was developed, which employs a Bronsted base catalyst generated in situ from a chiral Schiff base and t-BuOK. This reaction is a...

  开发了炔基酯的对映选择性分子内环化反应，该反应使用了从手性席夫碱和t-BuOK原位生成的布朗斯台德碱催化剂。这个反应是...
• Dual Photoredox/Gold Catalysis Arylative Cyclization of <i>o</i>-Alkynylphenols with Aryldiazonium Salts: A Flexible Synthesis of Benzofurans
  作者：Zhonghua Xia、Omar Khaled、Virginie Mouriès-Mansuy、Cyril Ollivier、Louis Fensterbank

  DOI：10.1021/acs.joc.6b01060

  日期：2016.8.19

  A new method for the arylative cyclization of o-alkynylphenols with aryldiazonium salts via dual photoredox/gold catalysis is described. The reaction proceeds smoothly at room temperature in the absence of base and/or additives and offers an efficient approach to benzofuran derivatives. The scope of the transformation is wide, and the limitations are discussed. The reaction is proposed to proceed through

  描述了一种通过双重光氧化还原/金催化的芳基重氮盐对邻炔基苯酚进行芳基环化的新方法。反应在室温下在没有碱和/或添加剂的情况下平稳进行，并为苯并呋喃衍生物提供了一种有效的方法。转换的范围很广，并讨论了局限性。提议该反应通过光还原还原产生的乙烯基金（III）中间体进行，该中间体经过还原消除以提供杂环偶联加合物。
• Tandem Gold-Catalyzed Hydrosilyloxylation-Aldol and -Mannich Reaction with Alkynylaryloxysilanols in 6-<i>exo</i>Mode
  作者：Euichul Lee、Taekyu Ryu、Youngchul Park、Sangjune Park、Phil Ho Lee

  DOI：10.1002/adsc.201300244

  日期：2013.5.17

  The tandem gold‐catalyzed hydrosilyloxylation–aldol and hydrosilyloxylation–Mannich reactions were developed through the formation of an enol silyl ether catalytically generated in situ from alkynylaryloxysilanols in the 6‐exo mode in one reaction vessel.

  通过在一个反应​​容器中以6- exo模式由炔基芳基氧基硅烷醇原位催化生成的烯醇甲硅烷基醚的形成，开发了串联金催化的氢甲硅烷基氧基化-羟醛和氢甲硅烷基氧基化-曼尼希反应。
• Gold-Catalyzed Enynal and Enynol Coupling by Selectively Steering Two Transient Vinyl-Gold Intermediates
  作者：Zipeng Wang、Tongxiang Cao、Shifa Zhu

  DOI：10.1021/acs.orglett.2c03890

  日期：2022.12.23

  bond is easily accessible but less exploited in homogeneous gold catalysis, which possesses weak nucleophilicity and would be likely to undergo protodemetalation. Herein, a gold-catalyzed enynal and enynol coupling by selectively steering two transient vinyl-gold intermediates is realized under mild conditions. It exhibits high atom economy and good tolerance of functional groups with the added benefit

  乙烯基-金键很容易获得，但在均相金催化中利用较少，它具有弱亲核性，很可能会发生原脱金属。在此，通过选择性地控制两种瞬态乙烯基金中间体，在温和条件下实现了金催化的烯醛和烯醇偶联。它表现出高原子经济性和官能团的良好耐受性，并具有操作简单的额外好处。对照实验表明，原位形成的乙烯基金是反应性的原因。