Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 2495-35-4 | MDL No. : | MFCD00048147 |
Formula : | C10H10O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GCTPMLUUWLLESL-UHFFFAOYSA-N |
M.W : | 162.19 | Pubchem ID : | 75617 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 46.64 |
TPSA : | 26.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.48 cm/s |
Log Po/w (iLOGP) : | 2.29 |
Log Po/w (XLOGP3) : | 2.55 |
Log Po/w (WLOGP) : | 1.76 |
Log Po/w (MLOGP) : | 2.2 |
Log Po/w (SILICOS-IT) : | 2.37 |
Consensus Log Po/w : | 2.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.56 |
Solubility : | 0.449 mg/ml ; 0.00277 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.75 |
Solubility : | 0.289 mg/ml ; 0.00178 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.93 |
Solubility : | 0.192 mg/ml ; 0.00118 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.43 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P273-P280-P302+P352-P304+P340-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium tetrahydroborate; copper(ll) sulfate pentahydrate; cobalt(II) chloride hexahydrate; In methanol; at 20℃; for 0.166667h; | General procedure: The catalyst precursor in form of a 0.04 M CuSO4 and 0.004 M CoCl2 solution was added to a solution of the alkene/alkyne compound in methanol. The reaction was started by adding an initial portion of NaBH4, resulting in a color change to black (in situ prepared catalyst) and vigorous gas evolution. Additional portions of NaBH4 were added in intervals of typically three or four minutes. The reaction itself was carried out at room temperature and normal atmosphere. However, generation of heat due to the exothermic character of the reaction usually heated the reaction mixture to 30-40 C. Cooling is generally not necessary in small scale. For large scale reactions a reflux condenser was used. The higher reaction temperature did not influence the reaction yield. The reaction mixture was finally quenched by adding 2 M H2SO4. Work up was carried out by extracting the water/methanol phase with DCM. The catalyst in general stays within the water/methanol layer. Drying the DCM layer with MgSO4 followed by filtration removes all remaining catalyst particles. The drying agent was filtered of and the DCM was removed in vacuo. |
91% | With hydrogen; In methanol; at 20℃; for 3h; | General procedure: The mixture of the substrate (0.250 mmol), 0.5% Pd/MS3A or 0.5% Pd/MS5A (10 wt % of the substrate) and MeOH (1 mL) was stirred under H2 atmosphere (balloon) at room temperature. After a given period, the reaction mixture was filtered through a membrane filter (Millipore, Millex-LH, 0.45 mm), and the filtrate was concentrated in vacuo to produce the corresponding reduced product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,5-dimethyl-2,5-di(2-ethyl hexanoyl peroxy)-hexane; at 75℃; for 2h; | A mix consisting of the prepolymer of Example 3, benzyl acrylate, <strong>[2495-37-6]benzyl methacrylate</strong> andN, N,-dimethylacrylamide at a weight ratio of 50/20/10/20 is prepared. To the mix is added Lupersol256 tu (Atochem) at 1 <Desc/Clms Page number 16>percent of the total weigh. The mix is then cured between two silane-treated glass plates in an oven at 75 C for 2 hours. The cured films are then released, extracted in isopropanol for over 4 hours and dried in a vacuum oven at 70 C overnight. All dried films are then placed in a borate buffered saline overnight before characterization. Films of different thickness can be made in this manner. To mimic actual uses, films of 600 to 1000 microns in thickness should be made and the UV-VIS transmittance measured. With 0.15 % by weight of dye moiety in the film, the UV-VIS transmittance should be less than approximately 50 to 60 percent at 450 nm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.0%Chromat. | Aliquat 336; sodium iodide; In water; at 50℃; for 2.5h; | In Example 8, benzyl acrylate was prepared by dissolving <strong>[7446-81-3]sodium acrylate</strong> (10 mmoles = 0.95 g) in water (101.3 g). The reaction flask was immersed in the water bath at 50°C and magnetically stirred. Then, a mixture consisting of benzyl chloride (50 mmoles = 6.29 g), Aliquat 336 (2 mmoles = 0.85 g), and sodium iodide (2 mmoles = 0.30 g) was added to the water phase. The reaction mixture was stirred magnetically at 50°C. The reaction mixture after 150 minutes consisted of benzyl acrylate in a 85.0percent theoretical yield based on <strong>[7446-81-3]sodium acrylate</strong>. Analysis was done with an external standard of Durene (tetramethylbenzene) on a Gas Chromatograph. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With triethylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); at 90℃; for 18h; | Example 33; (3aR,9bS)-4-Methyl-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-one hydrochloride; Part A. (E)-Ethyl 2-(3-(benzyloxy)-3-oxoprop-1-enyl)benzoate; To a solution of ethyl 2-bromobenzoate (1.15 g, 5.0 mmol) in 20 mL of DMF was added benzyl acrylate (1.22 g, 7.5 mmol) and triethylamine (1.39 mL, 10.0 mmol). The mixture was degassed and then there was added [1,1'-bis(diphenylphoshino)ferrocene]dichloropalladium (II), complex with dichloromethane (12.2 mg, 0.015 mol). The reaction mixture was stirred at 90 C. for 18 h. The reaction mixture was allowed to cool and was diluted with EtOAc. The organics were washed with water and brine, dried (MgSO4) and concentrated to an oil. The residue was purified (ISCO, elution with 0-15% EtOAc/hexane) to give 1.44 g (92%) of the title compound. 1H NMR (CDCl3): delta 8.51 (d, 1H), 7.96 (d, 1H), 7.57 (d, 1H), 7.50 (t, 1H), 7.45-7.22 (overlapping m, 6H), 6.35 (d, 1H), 5.26 (s, 2H), 4.38 (q, 2H), 1.37 (t, 3H). LRMS (ESI): 311.2 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With potassium hydroxide; In methanol; | Step 9: Preparation of α-methylenebenzenepropanoic acid The ethyl α-methylenebenzenepropanoate of Step 8 (4.6 g, 24.3 mmol) was dissolved in methanol (12 mL) and then reacted with 2N potassium hydroxide (24 mL) solution. The mixture was stirred at room temperature for 4 hours and concentrated by evaporation. The residue was diluted with water and washed with ether. The aqueous layer was acidified to pH 2 with 1N HCl, and then extracted with ethyl acetate. The extracts were dried (MgSO4) and evaporated to give the title compound as colorless oil (2.8 g, 66% yield). 1 H NMR: 300MHz spectrum consistent with proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In acetonitrile; | PREPARATION 10 Benzyl (E)-3-(2-methyl-1H-indol-4-yl)-2-propenoate A mixture of <strong>[6127-18-0]4-bromo-2-methyl-1H-indole</strong> (containing 25% of the 6-bromo isomer) (8.30 g), palladium (II) acetate (0.45 g), tri-o-tolylphosphine (1.22 g), benzyl acrylate (9.76 g) and triethylamine (8.36 ml) in acetonitrile (8 ml) was heated in an oil bath at 140 C. under an atmosphere of nitrogen for 2 hours. The mixture was cooled and partitionedbetween dichloromethane and water. The organic layer was separated, washed three times with water and dried (MgSO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with dichloromethane/hexane (1:1) first gave impurity followed by pure product.The product fractions were evaporated and the residue was triturated with ether to give the title compound (6.60 g), m.p. 135-136 C.Found: C,77.98; H,6.10; N,4.71. C19 H17 NO2 requires: C,78.33; H,5.88; N,4.81%. Further elution with dichloromethane/hexane (4:1) gave benzyl (E)-3-(2-methyl-1H-indol-6-yl)-2-propenoate (2.0 g), m.p. 164-165 C. Found: C,78.53; H,6.06; N,4.74. C19 H17 NO2 requires: C,78.33; H,5.88; N,4.81%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine;palladium diacetate; In N,N-dimethyl-formamide; propiononitrile; at 100℃; for 16h; | 6-Bromo - (4'-N-Boc-3-spiropiperidinyl)-l,8-naphthyridin-2(lH)-one (2.8 g, 7 mmol) was dissolved into 4:1 DMF/propionitrile (37 mL) and degassed with argon. Diisopropylethylamine (4.9 mL, 28 mmol) and benzyl acrylate (4.8 g, 28 mmol) were added and the solution was degassed with argon. Palladium acetate (150 mg, 0.7 mmol) and tri-o-tolylphosphine (425 mg, 1.4 mmol) were added the solution was degassed. The mixture was heated in a sealed tube at 1000C for 16 h. The solution was filtered through celite. The filter cake was washed with methylene chloride and the filtrate was concentrated to dryness to afford the title compound as a grey solid (1.7 g, 50%): 1H NMR (400 MHz, OMSO-d6) delta 9.88 (s, IH), 8.41 (s, IH), 7.68 (s, IH) 7.67 (d, J == 15.6 Hz, IH), 7.45-7.32 (in, 5H), 6.47 (d, J = 15.6 Hz, IH), 5.27 (s, 2H), 3.68- 3.62 (m, 2H), 3.52-3.46 (m, 2H), 2.90 (s, 2H), 2.05-1.92 (m, 2H), 1.47 (s, 9H), 1.48-1.45 (m, 2H); ESI MS m/z 478 [C27H3 .N3O5-^H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of 4-bromo-1 -naphthalenecarboxylic acid (100 g), benzylacrylate (96.8 g), triphenylphosphine (10.2 g) palladium(ll)acetate (2 g), triethylamine (258 ml) and DMF (600 ml) are heated at 90-100 0C for 4-12 h (typically 10-12 h). Two further portions of palladium(ll)acetate (20 g) are added at four hour intervals during the stir period. The mixture is treated with charcoal (3 x 15 g) at 50-80 0C (typically 70-80 0C) filtering after each charge at 40-45 0C. The DMF is then distilled off at 80-90 0C under vacuum and the residue is cooled to 25-35 0C. Dichloromethane (100 ml) and water (100 ml) are added to the residue and the mixture is acidified with concentrated hydrochloric acid and is stirred at 20-35 0C for about 30 min. The mixture is filtered, and the solid product dried. The residue is dissolved in a mixture of DMF (600 ml) then water (400 ml) at 90-100 0C and stirred for 1-1.5 h. The solution is filtered at 80-85 0C, cooled to 20-35 0C, and stirred for about 2 h. The product is filtered off and dried (dry weight 43 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With edetate disodium; In tetrahydrofuran; for 0.5h; | A mixture of benzyl acrylate (60.4 g, 372 mmol) and glycolaldehyde diethyl acetal (10.16 g, 74.5 mmol) in dry THF (70 mL) was stirred vigorously and Triton B (1.7 mL, 5 molpercent) was added. The RM became dark brown gradually over about 0.5 minutes during which an exotherm was noted. The reaction mixture was concentrated in vacuo and purified directly over silica-gel (330 g, Companion) eluting from 0-100percent EtOAc/cyclohexane to give the title compound as acolourless oil.Yield 9.7 g (44percent)1H NMR (400 MHz, CDCI3) 57.34-7.29 (m, 5H), 5.13 (s, 2H), 4.58 (t, J = 5.2Hz, 1H), 3.80, (t, J = 6.4 Hz, 2H), 3.67 (m, 2H), 3.54 (m, 2H), 3.46 (d, J = 5.2 Hz, 2H), 2.64 (t, J = 6.4 Hz, 2H), 1.20 (t, J = 7 Hz, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With pyridine; In water; at 20℃; for 22h;Heating / reflux; | Example 81(3S,4S)-N-[3,5-bis(trifluoromethyl)benzyl]-1-[3-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidin-3-yl)propanoyl]-3-(4-fluoro-2-methylphenyl)-N-methylpiperidine-4-carboxamide(step 1)A solution of <strong>[695-53-4]5,5-dimethyloxazolidine-2,4-dione</strong> (1.0 g) and benzyl acrylate (5.18 g) in a mixture of pyridine (38.8 mL) and water (7.8 mL) was refluxed under heating for 19 hr, and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with aqueous citric acid solution and water and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10% ethyl acetate/hexane) to give benzyl 3-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidin-3-yl)propanoate (2.84 g, 100%) as a colorless oil.1H-NMR (300 MHz, CDCl3):delta 1.51 (6H, s), 2.75 (2H, t, J=6.8 Hz), 3.85 (2H, d, J=6.8 Hz), 5.10 (2H, s), 7.31-7.39 (5H, m) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With hydroquinone; In neat (no solvent); at 70℃; for 168h; | Compound 2(19.71g; 0.1131mol) was dissolved in benzyl acrylate (150ml) containing hydroquinone (0.25g). The resulting solution was stirred at 70C for 7 days. Excess benzyl acrylate was removed by distillation (61-63C; 0.1mmHg) resulting in the crude product as a brown oil. The product was purified by dry column vacuum chromatography, eluting from heptane to EtOAc with 5% increments, yielding compound 3 as a colorless oil (36.42g; 64% yield). 1H NMR (500MHz, CDCl3) delta=7.38-7.27 (m, 10H), 5.20 (br s, 1H, BocNH-CH2-CH(CH3)-N-), 5.11 (s, 4H, Ph-CH2-O-C(O)-), 3.20 (dd, 1H, BocHN-CH2-CH(CH3)-N-), 2.88-2.76 (m, 4H, BocHN-CH2-CH(CH3)-N-; -NCH2-CH2C(O)-O-), 2.61-2.53 (m, 2H, -NCH2-CH2C(O)-O-), 2.49-2.36 (m, 4H, -NCH2-CH2C(O)-O-), 1.43 (s, 9H, (CH3)3C-C(O)-NH-), 0.90 (d, 3H, BocHN-CH2-CH(CH3)-N-, 3J=6.2). 13C NMR (126MHz, CDCl3) delta=172.47 (Ph-CH2-O-C(O)-CH2-CH2-), 156.13, 135.90 (Ph-CH2-O-C(O)-CH2-CH2-), 128.58 (Ph-CH2-O-C(O)-CH2-CH2-), 128.41 (Ph-CH2-O-C(O)-CH2-CH2-), 128.28 (Ph-CH2-O-C(O)-CH2-CH2-), 78.82 ((CH3)3C-C(O)-NH-), 66.31 (Ph-CH2-O-C(O)-CH2-CH2-), 54.83 (BocHN-CH2-CH(CH3)-N-), 44.95 (-O-C(O)-CH2-CH2-N-), 43.18 (BocHN-CH2-CH(CH3)-N-), 34.12 (-O-C(O)-CH2-CH2-N-), 28.49 ((CH3)3C-C(O)-NH-), 10.79 (BocHN-CH2-CH(CH3)-N-). MS (FAB) m/z=499 [M+H]+. Elemental analysis: calculated (%): C: 67.45; H: 7.68; N: 5.62. Found (%): C: 67.68; H: 7.66; N: 5.49. [alpha]D20 -39.1 (c 1.03, CH3CN). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In acetonitrile; at 40℃; for 1h;Inert atmosphere; | 3-(4-acetamidopiperidin-1-yl)-N-(2-((2,4-dichloro-3-(((2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-4-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)propanamide (8) A stirred mixture of <strong>[5810-56-0]4-acetamidopiperidine</strong> (1.82 g, 12.8 mmol) and benzyl acrylate (2.57 g, 15.4 mmol) in acetonitrile (50 mL) was stirred overnight under nitrogen and at 40 C. for 1 h. The mixture was evaporated to dryness and the residue was purified by silica gel chromatograph eluting with a gradient of 0% to 30% dichloromethane/methanol/NH4OH (10:1:0.1) and dichloromethane to give benzyl 3-(4-acetamidopiperidin-1-yl)propanoate as an oil (3.81 g, 98%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tributyl-amine; tris-(o-tolyl)phosphine;palladium diacetate; In N,N-dimethyl-formamide; at 110.0℃; for 1h;Microwave irradiation; | To a solution of <strong>[1346819-04-2]5-bromo-N-methylpyrimidine-2-carboxamide</strong> (0.14 g, 0.64 mmol) in DMF (5 mL) was added acrylic acid benzyl ester (0.13 g, 0.78 mmol), Pd(OAc)2 (14.3 mg), tri-o-tolyl phosphine (49 mg, 0.16 mmol), tributyl amine (0.48 g, 2.59 mmol). The reaction mixture was heated in microwave oven at 110 C. for 1 h. The reaction mixture was cooled to room temperature, partitioned in water (50 mL) and ethyl acetate (50 mL). Ethyl acetate layer was separated, dried (MgSO4), concentrated to give 3-(2-methylcarbamoyl-pyrimidin 5-yl)acrylic acid benzyl ester as a solid, this was washed with hexanes and dried to give the 0.122 g of the product. LCMS (APCI) 298 (M+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.8 g of lithium chloride is added to a solution of 15.5 g of [1,4]-benzoquinone in 350 ml of THF, and it is degassed with nitrogen. 3.2 g of palladium acetate and 23.7 g of benzyl acrylate are added and it is degassed with nitrogen for about 30 minutes. Than a solution of 35.1 g of <strong>[117832-17-4]2-iodo-4,5-dimethylaniline</strong> (prepared according to J. Med. Chem. 2001, 44, 3856-3871) in 150 ml of THF is added and it is stirred overnight. It is filtered and the filtrate is evaporated. The solid residue thus obtained is triturated with ether. It is filtered, the filtrate is washed with a solution of NaOH 0.5N and then with water and with brine. It is evaporated and then the solid residue is purified by silica gel chromatography, eluting with a cyclohexane/EtOAc mixture (8/2; v/v). 57.6 g of the expected compound is obtained in the form of a white powder.1H NMR: DMSO-d6 (250 MHz): delta (ppm): 2.14 (3H, s); 2.19 (3H, s); 4.93 (1H, d); 5.18 (2H, s); 7.23 (1H, s); 7.30-7.45 (5H, m); 7.59 (1H, s); 7.72 (1H, dd); 10.05 (1H, d). | ||
With p-benzoquinone; lithium chloride;palladium diacetate; In tetrahydrofuran;Inert atmosphere; | Preparation 2.65,6-Dimethyl-1 /-/-indole-3-carboxylic acid.(VIII): X = CH; R4 = Me; R5 = Me.Step 1 : 3-[(2-lodo-4,5-dimethylphenyl)amino]benzyl acrylate (XVIII).60.8 g of lithium chloride is added to a solution of 15.5 g of [1 ,4]- benzoquinone in 350 ml of THF, and it is degassed with nitrogen. 3.2 g of palladium acetate and 23.7 g of benzyl acrylate are added and it is degassed with nitrogen for about 30 minutes. Then a solution of 35.1 g of 2-iodo-4,5- dimethylaniline (prepared according to J. Med. Chem 2001 , 44, 3856-3871 ) in 150 ml of THF is added and it is stirred overnight. It is filtered and the filtrate is evaporated. The solid residue thus obtained is triturated with ether. It is filtered, the filtrate is washed with a solution of NaOH 0.5N and then with water and with brine. It is evaporated and then the solid residue is purified by silica gel chromatography, eluting with a cyclohexane/EtOAc mixture (8/2; v/v). 57.6 g of the expected compound is obtained in the form of a white powder.1H NMR: DMSO-de (250 MHz): delta (ppm): 2.14 (3H, s); 2.19 (3H, s); 4.93 (1 H, d); 5.18 (2H, s); 7.23 (1 H, s); 7.30-7.45 (5H, m); 7.59 (1 H, s); 7.72 (1 H, dd); 10.05 (1 H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4%; 90% | General procedure: TMSOTf (336 mg, 1.51 mmol) is added to a solution of the alcohol (0.755 mmol) in the respective nitrile (3 mL) and the mixture is stirred at rt for 65 h. H2O (25 mL) and brine (25 mL) are added, and the mixture is extracted with EtOAc (3 × 30 mL). The combined organic layers are dried (Na2SO4) and concentrated. The crude product is purified by flash column chromatography (silica gel). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.25 g | With triethylamine; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium(0); In N,N-dimethyl-formamide; at 100℃;Inert atmosphere; | Preparation Example 27 N,N-Dimethylformamide (10.0 mL) was bubbled with argon, and then <strong>[13631-21-5]4-<strong>[13631-21-5]bromo-3-chlorophenol</strong></strong> (1.00 g), benzyl acrylate (1.00 mL), bis(dibenzylideneacetone)palladium (0) (85.0 mg), tris(2-methylphenyl)phosphine (150 mg), and triethylamine (0.700 mL) were added thereto, followed by stirring at 100C overnight under an argon atmosphere. The reaction suspension was air-cooled to room temperature, and then water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain benzyl (2E)-3-(2-chloro-4-hydroxyphenyl)acrylate (1.25 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In dimethyl sulfoxide; at 100℃; for 15h;Inert atmosphere; | General procedure: A solution of aryl bromide (1mmol, 1equiv), acrylate (2equiv), PdCl2(PPh3)2 (5mol%) and Et3N (5equiv) in DMSO (2mL) under argon was heated at 100C for 15h. Water (10mL) was then added followed by sodium chloride (until saturation) and the reaction mixture was extracted with ethyl acetate (3×15mL). The organic layers were combined and washed with brine, dried over MgSO4, filtered and the solvent was removed under reduced pressure. The residue was purified on a column of silica gel to afford the desired pure coupling product. 4.2.3 2-((E)-2-Benzyloxycarbonylvinyl)benzoic acid tert-butyl ester 9c 8g General Heck procedure using General Heck procedure using <strong>[55666-42-7]ter<strong>[55666-42-7]t-butyl 2-bromobenzoate</strong></strong> 14 (500 mg, 1.95 mmol, 1 equiv) and benzyl acrylate 19c (0.6 mL, 2 mmol, 2 equiv) affords 9c (552 mg, 1.63 mmol, yield = 84%) as a colorless oil. 1H NMR (300 MHz, CDCl3): delta = 8.49 (d, J = 15.9 Hz, 1H), 7.96-7.91 (m, 1H), 7.62-7.32 (m, 8H), 6.38 (d, J = 15.9 Hz, 1H), 5.31 (s, 2H), 1.62 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In acetonitrile; at 90℃; for 3h;Inert atmosphere; Microwave irradiation; | Benzyl (E)-3-(6-phenylpyridin-3-yl)acrylate 5-Bromo-2-phenylpyridine (1 g, 4.27 mmol), benzyl acrylate (785 muIota, 5.13 mmol), tri(o-tolyl)phosphine (131 mg, 0.43 mmol) and triethylamine (2.25 ml, 17.09 mmol) were combined in acetonitrile (8 ml). The reaction mixture was thoroughly degassed by bubbling nitrogen through for 5 min prior to the addition of palladium acetate (97 mg, 0.43 mmol). The reaction mixture was transferred to the CEM microwave for 3 h at 90 C. The reaction mixture was filtered through celite and the filtrate was collected and all volatiles were removed. The crude material was purified by column chromatography, eluting 5-10% ethyl acetate/petroleum spirits to yield the title compound as a colourless solid (756 mg, 56%). LRMS [M+H]+ 316.2 m/z; 1H NMR (400 MHz, CDCI3) delta 8.78 (d, J = 2.1 Hz, 1 H), 8.12 - 7.95 (m, 2H), 7.88 (dd, J= 8.3, 2.3 Hz, 1 H), 7.82 - 7.66 (m, 2H), 7.54 - 7.28 (m, 8H), 6.56 (d, J = 16.1 Hz, 1 H), 5.26 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In acetonitrile; at 90℃; for 3h;Inert atmosphere; Microwave irradiation; | Benzyl (E)-3-(6-phenylpyridin-2-yl)acrylate <strong>[39774-26-0]2-Bromo-6-phenylpyridine</strong> (1 .69 g, 7.22 mmol), benzyl acrylate (1 .35 ml, 8.66 mmol), tri(o-tolyl)phosphine (220 mg, 0.72 mmol) and triethylamine (3.85 ml, 28.88 mmol) were all combined in acetonitrile (5 ml). The reaction mixture was degassed by bubbling nitrogen through it for 2 min prior to the addition of palladium acetate (162 mg, 0.72 mmol). The reaction mixture was transferred to the CEM microwave for 3 h at 90 C. The reaction was complete by TLC and the reaction mixture was filtered through celite and the filtrate collected. All of the volatiles were removed in vacuo and the crude material was purified by column chromatography, eluting 0-10% ethyl acetate/petroleum spirits to yield the title compound as a yellow oil (1 .13 g, 50%). LRMS [M+H]+ 316.2 m/z; HRMS [M+H]+ 316.1332 m/z, found 316.1336 m/z; 1 H NMR (400 MHz, CDCI3) delta 8.09 - 8.01 (m, 2H), 7.81 - 7.68 (m, 3H), 7.52 - 7.27 (m, 9H), 7.15 (d, J = 15.6 Hz, 1 H), 5.27 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With 10H-phenothiazine; N,N,N',N'-tetramethylhexamethylenediamine; zinc diacetate; oxygen; 4-methoxy-phenol; at 75 - 83℃; for 1h; | General procedure: Rotor,thermometer,Gas introduction pipe,In a 20 milliliter test tube fitted with a cooling tube,2.11 parts (0.0195 mol) of benzyl alcohol,4.57 parts (0.0351 mol) of 2-methoxyethyl acrylate,0.0109 parts (0.0001 mol) of DABCO as the catalyst A,0.0358 parts (0.0002 mol) of zinc acetate as the catalyst B,Hydroquinone monomethyl ether0.0016 part (238 wt ppm with respect to the total weight of raw materials charged),0.0001 part of phenothiazine(17 wt ppm with respect to the total weight of raw materials charged)Do not bubble oxygen containing gas (oxygen 5 vol%, nitrogen 95 vol%) into the liquidThe stirring was carried out for 1 hour in the range of the reaction solution temperature of 75 to 83 C.After that, 2-methoxyethanol contained in the reaction solution was quantitated,The reaction yield was 20%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) hexafluorophosphate; copper diacetate; In 1,2-dichloro-ethane; at 80℃; for 24h;Inert atmosphere; Schlenk technique; | General procedure: In a carius tube, acetanilide (27 mg, 0.2 mmol), [Cp*IrCl2]2 (5 mg, 0.006 mmol), AgPF6 (10 mg, 0.04 mmol) and Cu(OAc)2 (75 mg, 0.4 mmol) were dissolved in DCE (3 mL). To this suspension was added methyl acrylate (28 µL, 0.3 mmol) and the mixture degassed (3xfpt). It was then heated at 80 C for 24 h, filtered through celite, and the solvent evaporated to give the crude product which was purified by column chromatography on silica gel using ethylacetate/hexane (2:3, v/v) as eluent. A similar procedure was used for the other acetanilides, acetophenones and benzamides. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34.6%; 44.7% | With sodium hydride; In benzene; at 25 - 80℃; for 5h; | Sodium hydride (400 mg, 9.99 mmol) was added to <strong>[1212-53-9]methyl 2-(((benzyloxy)carbonyl)amino)acetate</strong> 11c (2.23 g, 9.99 mmol) in benzene (48 mL), followed by benzyl acrylate 12b (1.8 mL, 11.99mmol) and the reaction mixture was stirred for one hour, thenthe reaction mixture was heated at 80 °C for four hours. Then, the reaction mixture was cooled, 10percent citric acid added, extracted with diethyl ether, dried over magnesium sulfate, filtered, and concentrated.The residue was purified by RP HPLC eluting with acetonitrile: water with 0.1percent trifluoroacetic acid (5:95:100:0) to givedibenzyl 4-oxopyrrolidine-1,3-dicarboxylate 13f (1.66 g, 4.46mmol, 44.7percent yield) and 1-benzyl 3-methyl 4-oxopyrrolidine-1,3-dicarboxylate 13g (1.01 g, 3.46 mmol, 34.6percent yield).5.94. Dibenzyl 4-oxopyrrolidine-1,3-dicarboxylate 13f1H NMR (400 MHz, CD3SOCD3) d 11.17 & 11.12 (s, 1H), 7.42?7.24 (m, 10H), 5.22?5.04 (m, 4H), 4.24?3.82 (m, 4H); LC?MS (LC?ES) MH = 352.5.95. 1-Benzyl 3-methyl 4-oxopyrrolidine-1,3-dicarboxylate 13g1H NMR (400 MHz, CD3SOCD3) d 11.04 & 10.98 (s, 1H), 7.42?7.24 (m, 5H), 5.18?5.04 (m, 2H), 4.24?4.08 (m, 2H), 4.08?3.80(m, 2H), 3.66 & 3.61 (s, 3H); LC?MS (LC?ES) MH = 276. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With tetrabutylammomium bromide; sodium acetate; palladium diacetate; In N,N-dimethyl acetamide; at 100 - 105℃; for 5h;Schlenk technique; Inert atmosphere; | To a schlenk tube were added NaOAc (24.3 mmol, 2.0 g), tetrabutylammonium bromide (TBAB) (0.8 mmol, 260 mg), and Pd(OAc)2 (0.2 mmol, 54.5 mg) at room temperature under nitrogen atmosphere. A solution of <strong>[651341-68-3]ethyl 2-bromo-4-fluorobenzoate</strong> [14a] (8.1 mmol, 2.0 g) and benzyl acrylate [15a] (16.2 mmol, 2.6 g) in DMAc (40 mL) was added to the reaction mixture. The reaction mixture was stirred at 100 to 105 C for 5 hours and then cooled to room temperature. The reaction mixture was quenched with purified water and extracted with ethyl acetate three times. The combined organic layers were dried over anhydrous Na2S04. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography on silica gel by eluting with ethyl acetate/hexanes (v/v, 1/5) to afford ethyl (E)-2-(3-(benzyloxy)-3-oxoprop-l-en-l-yl)-4-fluorobenzoate [16a] in 94.0 % yield (2.5 g) as ayellow oil. XH NMR (600 MHz, CDCl3) d 8.48 (d, J= 16.2 Hz, 1H), 8.01 (dd, J= 9.0, 6.0 Hz, 1H), 7.42 (d, J= 6.6 Hz, 2H), 7.38 (t , J= 7.8 Hz, 2H), 7.33 (t, J= 3.0 Hz, 3H), 7.25 (dd, J= 9.6, 3.0 Hz, 1H), 7.10-7.13 (m, 1H), 6.32 (d, J= 15.6 Hz, 1H), 5.26 (s, 2H), 4.37 (q, J= 7.2 Hz, 2H), 1.37 (t, J= 7.2 Hz, 3H); 13C NMR (150 MHz, CDCl3) d 165.9, 165.8, 164.7 (d, JC F = 252.2 Hz), 143.3 (d, JC F = 1.8 Hz), 139.2 (d, JC F = 8.6 Hz), 135.9, 133.5 (d, CF = 9.2 Hz), 128.6, 128.3, 128.2, 126.3 (d, CF = 3.0 Hz), 121.6, 116.4 (d, CF = 21.6 Hz), 114.7 (d, CF = 22.7 Hz), 66.5, 61.6, 14.2; 19F NMR (564 MHz, CDC13) d - 106.3; LRMS (ESI) m/z calcd for CI9HI7F04 [M+H]+: 329.11; Found: 329.13. |
Tags: 2495-35-4 synthesis path| 2495-35-4 SDS| 2495-35-4 COA| 2495-35-4 purity| 2495-35-4 application| 2495-35-4 NMR| 2495-35-4 COA| 2495-35-4 structure
[ 2694-54-4 ]
Triallyl benzene-1,2,4-tricarboxylate
Similarity: 0.83
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :