2-(chloromethyl)-5-hydroxy-4-methoxypyrylium 2b (200 mg, 0.616 mmol), and phenylacetylene (1.35 mL, 12.3 mmol) were dissolved in CHCl3 (3.08 mL). N,N-Diisopropylaniline (240 μL, 1.23 mmol) was added to the reaction, the reaction vessel was sealed, and the reaction mixture was heated under microwave irradiation at 100ºC (controlled temperature) for 4 h. The reaction mixture was then concentrated and purified by chromatography (silica gel, 18 × 1.8 cm, 50 mL Hexanes, 200 mL 2% EtOAc in Hexanes, 100 mL 10% EtOAc in Hexanes, 200 mL 15% EtOAc in Hexanes) to lead to 4g as a highly viscous yellow oil (114 mg, 67% yield). Rf = 0.14 in 20% EtOAc in Hexanes. FTIR (KBr, thin film) 656(w), 798(s), 1078(m), 1261(s), 1607(b), 1709(b) 1960(w), 2254(w), 2838(w), 2962(s) cm−1. 1H NMR (400 MHz, CDCl3) δ 7.36 – 7.09 (m, 5H), 6.22 (d, J = 2.4 Hz, 1H), 6.11 (s, 1H), 4.98 (d, J = 2.4 Hz, 1H), 3.94 (d, J = 12.4 Hz, 1H), 3.77 (d, J = 12.4 Hz, 1H), 3.52 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 189.2, 156.3, 146.9, 132.7, 129.4, 129.2, 125.9, 124.9, 114.8, 88.7, 86.4, 55.2, 45.9. HRMS (ESI+): calc’d for C15H13ClO3 : 276.0553; Found: 276.0552.
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Phenylacetylene
Phenylacetylene
Phenylacetylene is a organic compound with the chemical formula C6H5CCH.
It is a colorless liquid with a characteristic aromatic odor.
Phenylacetylene is used in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds.
It is also employed as a monomer in the production of certain polymers.
Phenylacetylene has been studied for its potential applications in materials science and nanotechnology.
Researchers are investigating its use in areas such as organic electronics, catalysis, and molecular electronics.
Despite its utility, the analysis and optimization of Phenylacetylene-related protocols can be challenging.
The PubCompare.ai platform offers an AI-driven solution to help scientists streamline their Phenylacetylene research by identifying the best available protocols and products from the literature, preprints, and patents.
It is a colorless liquid with a characteristic aromatic odor.
Phenylacetylene is used in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds.
It is also employed as a monomer in the production of certain polymers.
Phenylacetylene has been studied for its potential applications in materials science and nanotechnology.
Researchers are investigating its use in areas such as organic electronics, catalysis, and molecular electronics.
Despite its utility, the analysis and optimization of Phenylacetylene-related protocols can be challenging.
The PubCompare.ai platform offers an AI-driven solution to help scientists streamline their Phenylacetylene research by identifying the best available protocols and products from the literature, preprints, and patents.
Most cited protocols related to «Phenylacetylene»
1H NMR
Blood Vessel
Carbon-13 Magnetic Resonance Spectroscopy
Chloroform
Chromatography
Hexanes
Microwaves
phenylacetylene
Silica Gel
Spectroscopy, Fourier Transform Infrared
Viscosity
To determine the copper leakage from the catalyst during the reaction, leaching test was performed hot filtration test for click reaction of benzyl halide 1 , phenylacetylene 3 and Sodium azide. The catalytically active particles were removed from the reaction by filtration after 10 min using a hot frit. After hot filtration, the yield of the reaction no longer changes and stagnates at around 40%.
Copper
Filtration
phenylacetylene
Sodium Azide
Materials and MethodsAll the chemicals including protected amino acids, Wang resin, and reagents for peptide synthesis were provided from Bachem AG, Switzerland or Santa Cruz Biotechnology Inc; U. S. A. The solvents were purchased from Sigma-Aldrich.
IR spectra of the samples were obtained using a Perkin–Elmer PE 843 IR spectrophotometer, UK. Mass spectra of the samples were recorded on an Agilent 6410 QQQ LCMass spectrometer.
Synthesis of triazole peptidesPreparation of 4-azido benzoic acidThe azido compound was prepared according to the published method with some modification (30). In brief, 4-aminobenzoic acid (1.64 g, 12.0 mmol) was dissolved in 10 mL water with concentrated hydrochloric acid (6 mL, 12 N). The mixture was stirred at room temperature for 1 h, then cooled to 0-5 °C in ice bath, and to which, an aqueous Na NO2 solution (13 mmol, 10 mN) was added dropwise. After 5 min, an aqueous solution of sodium azide (13 mmol, 10 mL) was added to the reaction which was stirred for 5 min.
The precipitate was isolated by filtration, and extracted with Ethanol (20 mL). The solvent was removed by vacuum to give a light yellow solid (yield 75%). The crude solid was used for the next step of synthesis. IR (KBr): (cm-1) 1687, 1700 (C=O carboxylic), 2137(N3), 1585, 1613 (aromatic ring). LC-MS (ESI) m/z: 161.8(M-1).
Preparation 4-(4-phenyl-1H-1, 2, 3-triazol-1-yl) benzoic acid The triazole compound was synthesized in accordance with the method previously reported with some changes (
To a round bottom flask, 4-azidobenzoic acid (1 eq) and phenylacetylene (1 eq) in methanol: water (50:50), sodium ascorbate (50 mg) and CuSO4 (13.4 mg) were added in sequence. The reaction was stirred at room temperature overnight. The flask content was poured into water (20 mL) and then extracted with ethyl acetate (3 × 20 mL). The whole organic solvent was washed with saturated NaCl solution (2 × 15 mL) and dried on sodium sulphate powder. After filtration, the solvent was evaporated in vacuum and the crude precipated product was collected (yield 70%). IR (KBr): n (cm -1) 1545, 1594 (aromatic rings), 1420 (N=N). LC-MS (ESI) m/z: 265.9(M+1).
Peptide synthesis on resin Two peptides, GLTSK and GEGSGA, previously detected in common bean fractions as inhibitors of human colorectal cancer cells, were synthesized on solid phase method using Wang resin (32 (link)). The resin (0.5 g, 1.0-2.5 mmol/g substitution) was swollen in a reactor (fitted at the bottom with a fritted glass filter) by the solvent mixture DMF/ DCM (1: 9, 10 mL) for 1 h and then the solvent was drained off. The first amino acid (2.0 eq), HOBT (2.0 eq) and 4- dimethyl amino pyridine (DMAP) (0.1 eq) in 5 mL DMF were added to the reactor. Diisopropylcarbodiimide (DIC, 1.0 eq) was then added to the reaction vessel and the reactor was shaken for 3 h at room temperature. After 3 h, the mixture was added piperdine/acetic anhydride (2.0 eq: 2.0 eq) and the reaction was stirred for 30 min at room temperature. Following removing solvent by filtration, the resin was washed with DMF (3 × 5 mL), DCM (3 × 5 mL), and methanol (3 × 5 mL). Removing the Fmoc protecting group of the amino acid attached to the resin was performed by treating resin with a solution of piperazine/DMF (10%) for 20 min. The solution was then drained and the resin was washed with DMF (2 × 5 mL). The second amino acid was used with HOBt and DIC (without DMAP) for attaching to the first amino acid bound to the resin. It was followed by washing resin with DMF and DCM. Deprotection was also performed by the N-terminal Fmoc removal of the newly formed peptide bound to the resin. Other amino acids were used for bonding to the above peptide linked with resin followed by deprotection, accordingly.
Preparation of triazole peptides linked to the resinA mixture of the triazole compound, 4-(4-phenyl-1H-1, 2, 3-triazol-1-yl) benzoic acid (2 eq) with HOBt (2 eq) and DIC (2 eq) in 5 mL DMF was prepared and added to a part of peptide linked- resin in the reactor. The reaction was shaken for 3 h at room temperature. Then, the solvent was drained and the resin was washed with DMF (3 × 5 mL) and DCM (3 × 5 mL).
Cleavage of the peptides from the resinBoth classes of peptides and triazole conjugated peptides were cleaved from the resin by a solution (10 mL) of trifluoroacetic acid/DCM/anisole /triisopropylsilane (50:45:2.5:2.5) for 2 h. After filtration, the filtrate was added dropwise to an ice-cold diethyl ether. Thus, the precipitated peptides were collected by filtration, washed with cold ether, and kept in a cold and dried condition (
Cell toxicity studyTo determine the cytotoxicity of the peptides and their triazole conjugates, three human cancer cell lines were employed; MCF-7 and MDA-MB-231(two breast cancer Cell Lines), and HT-29 (Human Colorectal Adenocarcinoma Cell Line). Human skin fibroblast cell line was also included for comparison. Cell toxicity experiments were carried out in accordance with the previously reported methods with some modification (33, 34). At 37 °C under CO2/air (5:95%), the cells were grown in RPMI1640 medium, enriched with fetal bovine serum (FBS, 10%), penicillin (100 µg/mL), and streptomycin (100 µg/mL). The Cell viability was examined by employing the MTT technique which its principle is on the basis of the transformation of3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) dye to formazan formed as purple crystals by succinate dehydrogenase enzyme of mitochondria in the alive cells. The cells were breeded into 96-well plates at a concentration of 104 cells/well and incubated for 24 h. The cells were exposed to 10, 100, and 1000 nM concentrations of the peptides for 48 h. MTT (10 μL, 5 mg/mL in PBS) was added to each well at the end of each time analysis, and the microplate was kept at 37 °C for 4 h.
The medium solution containing MTT was discarded and DMSO (100 μL) was replaced to each well to dissolve the formazan crystals. The plates were then maintained for 20 min at 37 °C. At the end, the optical density of each well was read at 570 nm against the reference wavelength of 630 nm as the background employing a spectrophotometer plate reader (Infinite® M200, TECAN) (35). Ciprofloxacin as a positive cytotoxic control of the peptides was used. Data were shown as the mean of triplicate measuring of the number of living cells.
General procedure for hydration–condensation reaction of phenylacetylene (1a ) and benzaldehyde (2a ). A solution of phenylacetylene (1a ) (0.4 mmol) and benzaldehyde (2a ) (1.6 mmol) was pumped through the flow cell filled with amberlyst-15 resin (16–50 mesh) (10.0 g) and dry 1,2-dichloroethane at a flow rate of 0.5 mL min−1. During this period the reaction vessel in a microwave cavity was irradiated at 90 °C (50 W). Following the reaction, 100 mL solvent was pumped through the flow cell at the same flow rate in order to wash the system, and the combined solutions were evaporated in vacuo. The residue was purified by column chromatography (n-hexane/DCM [2:1 to 1:1]).
amberlyst-15
benzaldehyde
Blood Vessel
Cells
Chromatography
Dental Caries
Ethylene Dichlorides
Microwaves
n-hexane
phenylacetylene
Resins, Plant
Solvents
Most recents protocols related to «Phenylacetylene»
In a 10 mL Schlenk tube, under an inert atmosphere in dry CH3CN (1.0 mL), the aniline (1.0 mmol), phenylacetylene (1.5 mmol), AuNHC (1% mol), and AgSbF6 (1% mol) were dissolved. The flask was placed in an oil bath at 90 °C and the mixture was stirred for 16 h.
The solvent was removed, and crude oil was added to the dibromoethane (1.0 mmol) as an internal standard. The yields of imines were determined by 1H NMR analysis, after the dissolution of the sample in CDCl3. The NMR characterization of the imines is reported in the literature in Ref. [52 (link)].
The solvent was removed, and crude oil was added to the dibromoethane (1.0 mmol) as an internal standard. The yields of imines were determined by 1H NMR analysis, after the dissolution of the sample in CDCl3. The NMR characterization of the imines is reported in the literature in Ref. [52 (link)].
To a solution of organocatalyst (0.010 mmol SQ or TS or TU ) in the corresponding solvent (0.5 mL) metal acetate (0.005–0.012 mmol Cu(OAc)2 or Ni(OAc)2 or AgOAc) was added. To this solution aniline (12 , 11.3 mg, 11 μL, 0.121 mmol), benzaldehyde (13 , 10.6 mg, 10 μL, 0.100 mmol), finally phenylacetylene (14 , 14.9 mg, 16 μL, 0.146 mmol) were added. Then the resulting mixture was stirred at room temperature for 24 hours. The volatile components were removed under reduced pressure. The crude product was purified by preparative thin layer chromatography on silica gel using dichloromethane:hexane=2 : 1 (Rf=0.87) as eluent to obtain the adduct as a colorless liquid. Yields and enantiomeric excess (ee) values can be seen in Table 3 . These products had the same spectroscopic data than those of reported (the absolute configuration was determined by the optical rotation of the products).
[80] (link) Kromasil® AmyCoat 5 μm, Cellulose‐1 column (250×4.6 mm ID, a mixture of hexane:ethanol=85 : 15 as the eluent with a flow rate of 0.8 mL min−1, UV detector α=254 nm); UV detector 254 nm, 5 μL or 10 μL injection, 20 °C. Retention time for (S)‐15 : 8.5 min, for (R)‐15 : 9.7 min. The amounts of the catalysts and reaction times are shown in Table 3 and in Table S1 and Table S2 in Supporting Information.
[80] (link) Kromasil® AmyCoat 5 μm, Cellulose‐1 column (250×4.6 mm ID, a mixture of hexane:ethanol=85 : 15 as the eluent with a flow rate of 0.8 mL min−1, UV detector α=254 nm); UV detector 254 nm, 5 μL or 10 μL injection, 20 °C. Retention time for (S)‐
In this work, the models of PI resins were constructed by Materials Studio (MS) 2017 software package from BIOBIA (San Diego, CA, USA) software. As shown in Figure 3 a, the single-chain PI model was established. The stable structure as shown in Figure 3 b was obtained through geometric optimization and energy optimization. The optimized molecular chain was twisted, and the twist angle and spatial conformation changed. Then, the curing reaction process was simulated by the Forcite tool.
In order to further study the thermal decomposition mechanism of phenylacetylene-capped polyimide molecules, the thermal decomposition process of the PI molecular chain was simulated at different temperatures by selecting the GULP module. Because the PI molecular chain needed to receive enough energy in a very short time to cause pyrolysis, the simulated temperature was obviously higher than the actual temperature, and the high temperature would not affect the study of reaction mechanism. Finally, the DMol3 module was selected to calculate the bond energy of the initial fracture, so as to predict the initial reaction of thermal decomposition.
In order to further study the thermal decomposition mechanism of phenylacetylene-capped polyimide molecules, the thermal decomposition process of the PI molecular chain was simulated at different temperatures by selecting the GULP module. Because the PI molecular chain needed to receive enough energy in a very short time to cause pyrolysis, the simulated temperature was obviously higher than the actual temperature, and the high temperature would not affect the study of reaction mechanism. Finally, the DMol3 module was selected to calculate the bond energy of the initial fracture, so as to predict the initial reaction of thermal decomposition.
In an argon-filled glovebox, phenylacetylene
(0.03 g, 0.3 mmol),
complex4 (0.03–0.075 mmol), ferrocene (0.005
g, 0.03 mmol), and the deuterated solvent (1 mL) were charged into
a vial. The mixture was stirred during the specified time (3–6
h) at room temperature. Then, the conversion of phenylacetylene to
both isomers (1,3,5 and 1,2,4-triphenylbenzene) was determined by
analyzing a sample by 1H NMR spectroscopy with ferrocene
as the standard.
(0.03 g, 0.3 mmol),
complex
g, 0.03 mmol), and the deuterated solvent (1 mL) were charged into
a vial. The mixture was stirred during the specified time (3–6
h) at room temperature. Then, the conversion of phenylacetylene to
both isomers (1,3,5 and 1,2,4-triphenylbenzene) was determined by
analyzing a sample by 1H NMR spectroscopy with ferrocene
as the standard.
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Phenylacetylene is a chemical compound that consists of a phenyl group (C6H5-) and an acetylene group (-C≡CH). It is a colorless liquid with a characteristic odor. Phenylacetylene is commonly used as a precursor in organic synthesis and as a building block for various chemical products.
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Phenylacetylene is a chemical compound with the formula C₆H₅C≡CH. It is a colorless, flammable liquid with a characteristic odor. Phenylacetylene is used as a precursor in the synthesis of various organic compounds.
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More about "Phenylacetylene"
Phenylacetylene (also known as Phenylethyne or Ethynylbenzene) is a versatile organic compound with the chemical formula C6H5CCH.
This colorless liquid has a characteristic aromatic odor and finds applications in the synthesis of a variety of pharmaceuticals, agrochemicals, and other organic compounds.
It is also employed as a monomer in the production of certain polymers, making it a crucial building block in materials science and nanotechnology.
Researchers are actively investigating the potential uses of phenylacetylene in areas such as organic electronics, catalysis, and molecular electronics.
These studies often involve techniques like gas chromatography, using instruments like the Agilent GC System 7820A, to analyze and optimize protocols related to phenylacetylene.
Additionally, solvents like ethanol, chloroform, and toluene may be used in the extraction and purification of phenylacetylene.
The closely related compound, propargyl alcohol (CH≡CCH2OH), is another important precursor in organic synthesis, while acetone and ethylene glycol can be used in the production and processing of phenylacetylene-based materials.
Despite its utility, the analysis and optimization of phenylacetylene-related protocols can be challenging.
That's where the PubCompare.ai platform comes into play, offering an AI-driven solution to help scientists streamline their phenylacetylene research.
By identifying the best available protocols and products from the literature, preprints, and patents, PubCompare.ai can improve reproducibility and efficiency in phenylacetylene studies, empowering researchers to push the boundaries of materials science and nanotechnology.
This colorless liquid has a characteristic aromatic odor and finds applications in the synthesis of a variety of pharmaceuticals, agrochemicals, and other organic compounds.
It is also employed as a monomer in the production of certain polymers, making it a crucial building block in materials science and nanotechnology.
Researchers are actively investigating the potential uses of phenylacetylene in areas such as organic electronics, catalysis, and molecular electronics.
These studies often involve techniques like gas chromatography, using instruments like the Agilent GC System 7820A, to analyze and optimize protocols related to phenylacetylene.
Additionally, solvents like ethanol, chloroform, and toluene may be used in the extraction and purification of phenylacetylene.
The closely related compound, propargyl alcohol (CH≡CCH2OH), is another important precursor in organic synthesis, while acetone and ethylene glycol can be used in the production and processing of phenylacetylene-based materials.
Despite its utility, the analysis and optimization of phenylacetylene-related protocols can be challenging.
That's where the PubCompare.ai platform comes into play, offering an AI-driven solution to help scientists streamline their phenylacetylene research.
By identifying the best available protocols and products from the literature, preprints, and patents, PubCompare.ai can improve reproducibility and efficiency in phenylacetylene studies, empowering researchers to push the boundaries of materials science and nanotechnology.