2-(2-(三甲基甲硅烷基)乙炔基)苯基乙酸酯 | 81787-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 2-(2-(三甲基甲硅烷基)乙炔基)苯基乙酸酯
• 英文名称: 2-(2-(trimethylsilyl)ethynyl)phenyl acetate
• 英文别名: 2-[(trimethylsilyl)ethynyl]phenyl acetate；o-((trimethylsilyl)ethynyl)phenyl acetate；(2-acetoxyphenylethynyl)trimethylsilane；2-(trimethylsilylethynyl)phenyl acetate；2-((Trimethylsilyl)ethynyl)phenyl acetate；[2-(2-trimethylsilylethynyl)phenyl] acetate
• CAS: 81787-63-5
• 化学式: C₁₃H₁₆O₂Si
• 分子量: 232.354
• InChiKey: CMYHVCVONBDIRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-(三甲基甲硅烷基)乙炔基)苯基乙酸酯 在 dirhodium tetraacetate 、 正丁基锂 、 potassium fluoride dihydrate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.18h， 生成 3-(phenyl(methoxycarbonyl)methyl)benzofuran
  参考文献：
  名称：

  Benzofurans or Isochromenes via the Ring-Opening Cyclization of Cyclopropene Derivatives with Organolithiums

  摘要：

  A new and efficient approach to benzocycles from cyclopropene derivatives is described. Deprotection by organolithiums and subsequent ring-opening cyclization of the related 2-cyclopropenyl phenyl or benzyl acetates generated benzofurans and isochromenes in one pot.

  DOI：

  10.1021/ol2032009
• 作为产物：
  描述：

  2-碘苯酚 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 6.17h， 生成 2-(2-(三甲基甲硅烷基)乙炔基)苯基乙酸酯
  参考文献：
  名称：

  碘代炔烃的氧化作用：金（I）催化的苯并呋喃快速通道。

  摘要：

  （乙腈）[1，3-双（2，6-二异丙基苯基）-咪唑-2-亚基]金（I）催化2-（碘乙炔基）芳基酯的环异构化，得到3-碘-2-酰基苯并呋喃。这种催化转化是史无前例的选择性合成事件的结果，该合成事件包括[1,2]碘转移，C–O闭环步骤以及将酮官能团安装到新化合物中的C–C键形成。戒指。实验证据支持β-碘取代的亚乙烯基金作为中间物质的参与。该反应可耐受酚部分的不同取代方式和羧基片段上的多种基团，不仅包括烷基，而且还包括烯基，芳基和杂芳基。

  DOI：

  10.1021/acs.orglett.9b02551

文献信息

• Synthesis of chalcone ethynylogues with a pharmaceutical objective
  作者：Pierre Babin、Paulette Lapouyade、Jacques Dunoguès

  DOI：10.1139/v82-059

  日期：1982.2.15

  A simple route to chalcone ethynylogues, convenient even in the presence of alkoxy or acyloxy substituents, is proposed. This method is based on the use of ethynylsilanes, the involved trimethylsilyl group being recovered during the course of the reaction.

  提出了一种制备查尔酮乙炔类化合物的简单方法，即使存在烷氧基或酰氧基取代基也很方便。该方法基于使用乙炔基硅烷，其中涉及的三甲基硅基在反应过程中得以回收。
• A new structural alternative in benzo[b]furans for antimicrobial activity
  作者：M. Wahab Khan、M. Jahangir Alam、M.A. Rashid、R. Chowdhury

  DOI：10.1016/j.bmc.2005.05.009

  日期：2005.8

  Two series of 2-substituted and three new diacetyl benzofurans were synthesized through palladium-catalyzed reactions, and their in vitro antimicrobial spectra were assessed. The compounds demonstrated mild to significant growth inhibition against antibiotic-susceptible standard and clinically isolated strains of Gram-positive and Gram-negative bacteria as well as human fungal pathogens. Ampicillin and kanamycin were used as references for antibacterial screening; nystatin and amphotericin B were used for antifungal screening. Varying substitution at the benzofuran moiety and subsequent antimicrobial screening identified the C-3-acetyl functionality as a new structural alternative for optimal antimicrobial property in the benzofuran class of Compounds. (c) 2005 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Reaction of <i>o</i>-Ethynylphenols, <i>o</i>-((Trimethylsilyl)ethynyl)phenyl Acetates, and <i>o</i>-Alkynylphenols with Unsaturated Triflates or Halides:  A Route to 2-Substituted-, 2,3-Disubstituted-, and 2-Substituted-3-acylbenzo[<i>b</i>]furans
  作者：Antonio Arcadi、Sandro Cacchi、Mario Del Rosario、Giancarlo Fabrizi、Fabio Marinelli

  DOI：10.1021/jo961051a

  日期：1996.1.1

  The reaction of o-ethynylphenols 3 with a wide variety of unsaturated halides or triflates 6 in the presence of Pd(OAc)(2)(PPh(3))(2), CuI, and Et(3)N (procedure A) gives 2-vinyl- and 2-arylbenzo[b]furans 7, in good to high yield, through a palladium-catalyzed coupling followed by an in situ cyclization step. Small amounts of 2,3-disubstituted-benzo[b]furans 8 are usually isolated as side products. In some cases, however, compounds 8 are generated in significant yield or even as the main products. The formation of 8 can be prevented by employing alternative procedures (B and C) that use o-((trimethylsilyl)ethynyl)phenyl acetates 5 as starting building blocks. Procedure B is based on the palladium-catalyzed reaction of 5 with 6 in the presence of Pd(PPh(3))(4), Et(3)N, and n-Bu(4)NF, followed by the hydrolysis of the resultant coupling derivative 12 under basic conditions. Procedure C affords 7 through an in situ coupling/cyclization of 5 with 6 in the presence of Pd(PPh(3))(4) and KOBu(t). The utilization of o-alkynylphenols 9 as the starting alkynes in the palladium-catalyzed reaction with 6 leads to the formation of 2,3-disubstituted-benzo[b]furans 13 through an annulation process promoted by sigma-vinyl- and sigma-arylpalladium complexes generated in situ. The best results in this case are obtained by using KOAc and Pd(PPh(3))(4). In the presence of KOAc and Pd(PPh(3))(4), and under an atmosphere of carbon monoxide, the reaction of o-alkynylphenols with 6 provides 2-vinyl- and 2-aryl-3-acylbenzo[b]furans 14.
• BABIN, P.;LAPOUYADE, P.;DUNOGUES, J., CAN. J. CHEM., 1982, 60, N 4, 379-382
  作者：BABIN, P.、LAPOUYADE, P.、DUNOGUES, J.

  DOI：——

  日期：——
• Oxyacylation of Iodoalkynes: Gold(I)-Catalyzed Expeditious Access to Benzofurans
  作者：Paula Fernández-Canelas、Eduardo Rubio、José M. González

  DOI：10.1021/acs.orglett.9b02551

  日期：2019.8.16

  6-diisopropylphenyl)-imidazole-2-ylidene] gold(I) catalyzes the cycloisomerization of 2-(iodoethynyl)aryl esters to give 3-iodo-2-acyl benzofurans. This catalytic transformation is the result of an unprecedented selective synthetic event, which comprises a [1,2]-iodine shift, a C–O ring-closure step, and a C–C bond-formation that installs the ketone functionality into the new ring. Experimental evidence

  （乙腈）[1，3-双（2，6-二异丙基苯基）-咪唑-2-亚基]金（I）催化2-（碘乙炔基）芳基酯的环异构化，得到3-碘-2-酰基苯并呋喃。这种催化转化是史无前例的选择性合成事件的结果，该合成事件包括[1,2]碘转移，C–O闭环步骤以及将酮官能团安装到新化合物中的C–C键形成。戒指。实验证据支持β-碘取代的亚乙烯基金作为中间物质的参与。该反应可耐受酚部分的不同取代方式和羧基片段上的多种基团，不仅包括烷基，而且还包括烯基，芳基和杂芳基。