2-(2-(phenylethynyl)phenyl)ethan-1-ol | 1450719-52-4

• 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-(2-(phenylethynyl)phenyl)ethan-1-ol
• 英文别名: 2-[2-(2-phenylethynyl)phenyl]ethanol
• CAS: 1450719-52-4
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: ZQATWMACPIIVSN-UHFFFAOYSA-N

物化性质

• 沸点：
  394.4±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(2-(phenylethynyl)phenyl)ethan-1-ol 在 哌啶 、 二苯基二硒醚 、 戴斯-马丁氧化剂 、 溶剂黄146 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 2.0h， 生成 5-(2-(phenylethynyl)phenyl)furan-2(5H)-one
  参考文献：
  名称：

  Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium

  摘要：

  An efficient gold-catalyzed ring-expansion reaction of enyne-lactones to form 2-oxoninonium intermediates is reported. The 2-oxoninonium generated in this work could undergo further 6 pi electrocyclization and aromatization reaction to produce different aromatic compounds.

  DOI：

  10.1021/acs.orglett.7b02834
• 作为产物：
  描述：

  2-(2-碘苯基)乙酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.08h， 生成 2-(2-(phenylethynyl)phenyl)ethan-1-ol
  参考文献：
  名称：

  Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium

  摘要：

  An efficient gold-catalyzed ring-expansion reaction of enyne-lactones to form 2-oxoninonium intermediates is reported. The 2-oxoninonium generated in this work could undergo further 6 pi electrocyclization and aromatization reaction to produce different aromatic compounds.

  DOI：

  10.1021/acs.orglett.7b02834

文献信息

• Palladium-Catalyzed Alkyne Insertion/Reduction Route to Trisubstituted Olefins
  作者：Erin R. Fruchey、Brendan M. Monks、Andrea M. Patterson、Silas P. Cook

  DOI：10.1021/ol4018694

  日期：2013.9.6

  A new route to trisubstituted olefins through a palladium-catalyzed alkyne insertion/reduction reaction with unactivated alkyl iodides is reported. The reaction proceeds under mild conditions and tolerates a range of functional groups and substitution patterns. Preliminary mechanistic inquiry suggests that the transformation may proceed through a hybrid radical/organometallic pathway.

  报道了通过钯催化的炔烃插入/还原反应与未活化的烷基碘的三取代烯烃的新途径。该反应在温和的条件下进行，并能承受一定范围的官能团和取代方式。初步的机理研究表明，该转变可能通过杂化自由基/有机金属途径进行。
• Synthesis of 2-Alkylideneisochromans by Cyclocarbonylative Sonogashira Reactions
  作者：Laura Antonella Aronica、Luca Giannotti、Stefano Giuntini、Anna Maria Caporusso

  DOI：10.1002/ejoc.201402979

  日期：2014.11

  In this study we used a tandem carbonylative Sonogashira reaction/cyclisation process to construct alkylidene-functionalized isochromans in high yields with complete stereoselectivity (only Z isomers were formed). The reaction was performed in the absence of a CuI co-catalyst with a small amount of PdCl2(PPh3)2 (0.2–0.5 mol-%), and aryl iodides bearing both electron-donating and electron-withdrawing

  在这项研究中，我们使用串联羰基化 Sonogashira 反应/环化过程以高产率构建亚烷基官能化异色满，具有完全立体选择性（仅形成 Z 异构体）。该反应在没有 CuI 助催化剂和少量 PdCl2(PPh3)2 (0.2–0.5 mol-%) 的情况下进行，并且成功地使用了带有给电子和吸电子取代基的芳基碘化物。
• Palladium Nanoparticles in Glycerol: A Versatile Catalytic System for CX Bond Formation and Hydrogenation Processes
  作者：Faouzi Chahdoura、Christian Pradel、Montserrat Gómez

  DOI：10.1002/adsc.201300753

  日期：2013.12.16

  AbstractPalladium nanoparticles stabilised by tris(3‐sulfophenyl)phosphine trisodium salt in neat glycerol have been synthesised and fully characterised, starting from both Pd(II) and Pd(0) species. The versatility of this innovative catalytic colloidal solution has been proved by its efficient application in CX bond formation processes (X=C, N, P, S) and CC multiple bond hydrogenation reactions. The catalytic glycerol phase could be recycled more than ten times, preserving its activity and selectivity. The scope of each of these processes has demonstrated the power of the as‐prepared catalyst, isolating the corresponding expected products in yields higher than 90%. The dual catalytic behaviour of this glycerol phase, associated to the metallic nanocatalysts used in wet medium (molecular‐ and surface‐like behaviour), has allowed attractive applications in one‐pot multi‐step transformations catalysed by palladium, such as CC coupling followed by hydrogenation, without isolation of intermediates using only one catalytic precursor.magnified image
• Triaryl-Like MONO-, BIS-, and TRISKITPHOS Phosphines: Synthesis, Solution NMR Studies, and a Comparison in Gold-Catalyzed Carbon–Heteroatom Bond Forming 5-<i>exo</i>-dig and 6-<i>endo</i>-dig Cyclizations
  作者：Simon Doherty、Julian G. Knight、Daniel O. Perry、Nicholas A. B. Ward、Dror M. Bittner、William McFarlane、Corinne Wills、Michael R. Probert

  DOI：10.1021/acs.organomet.6b00146

  日期：2016.5.9

  A homologous series of triaryl-like KITPHOS-type monophosphines containing one, two, or three bulky 12-phenyl-9,10-dihydro-9,10-ethenoanthracene (KITPHOS) units have been developed, and the influence of increasing steric bulk on their efficacy as ligands in gold(I)-catalyzed carbon-heteroatom bond-forming cyclizations has been investigated. Detailed solution NMR studies on Ph-TRISKITPHOS, its oxide, and the corresponding gold(I) chloride adduct identified a conformational exchange process involving a concerted librational motion of the individual anthracene-derived organic substituents about their P-C bonds. The cessation of this motion at reduced temperatures lowers the molecular symmetry such that the two C6H4 rings in each of the KITPHOS units become inequivalent; a lower energy process involving restricted rotation of the biaryl-like phenyl ring has also been identified. Electrophilic gold(I) complexes of these triaryl-like KITPHOS monophosphines catalyze the 5-exo-dig cycloisomerization of propargyl amides to afford the corresponding methylene oxazolines, which were used in a subsequent tandem carbonyl-ene reaction to afford functionalized 2 -substituted oxazolines. A comparative survey revealed that catalyst efficiency for cycloisomerization decreases in the order MONOKITPHOS = BISKITPHOS > PPh3 > TRISKITPHOS. The optimum system also catalyzes the selective 6-endo-dig cyclization of 2-alkynylbenzyl alcohols, 2-alkynylbenzoic acid, and 2-phenylethynyl benzamides; gratifyingly, in several cases the yields obtained are markedly higher and/or reaction times significantly shorter than those previously reported for related gold catalysts. Moreover, these are the first examples of gold(I)-catalyzed 6-endo-dig cycloisomerizations involving 2-phenylethynyl benzamides and, reassuringly, the optimum gold(I)/MONOKITPHOS systems either rivaled or outperformed existing silver or palladium based catalysts. The steric parameters of this homologous series of phosphines have been quantified and compared with selected triarylphosphines using a combination of Solid -G calculations, to determine the percentage of the metal coordination sphere shielded by the phosphine (the G parameter), and Salerno molecular buried volume calculations (SambVca) to determine the percent buried volume (%V-bur); the corresponding Tolman cone angles have also been determined from correlations.
• Direct Construction of Fused Indoles by Gold-Catalyzed Cascade Cyclization of Conjugated Diynes
  作者：Saori Naoe、Tatsuo Saito、Masanobu Uchiyama、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1021/acs.orglett.5b00550

  日期：2015.4.3

  A gold-catalyzed cascade cyclization of aniline derivatives bearing a conjugated diyne moiety was developed. Following the 5-endo-dig indole formation, subsequent 7-endo-dig cyclization predominated over 6-exo-dig cyclization to give the indole fused with a seven-membered ring in good yields.