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CAS No. : | 33167-21-4 | MDL No. : | MFCD03424810 |
Formula : | C11H11ClO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WWFYJJHEBDWEJF-UHFFFAOYSA-N |
M.W : | 226.66 | Pubchem ID : | 2757831 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.27 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 57.35 |
TPSA : | 43.37 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.91 cm/s |
Log Po/w (iLOGP) : | 2.36 |
Log Po/w (XLOGP3) : | 2.5 |
Log Po/w (WLOGP) : | 2.48 |
Log Po/w (MLOGP) : | 2.16 |
Log Po/w (SILICOS-IT) : | 2.96 |
Consensus Log Po/w : | 2.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.79 |
Solubility : | 0.371 mg/ml ; 0.00164 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.06 |
Solubility : | 0.199 mg/ml ; 0.000879 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.85 |
Solubility : | 0.0316 mg/ml ; 0.00014 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.68 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
2-(3'-Chlorophenyl)-7-methyl-pyrido[1,2-a]pyrimidin-4-one (10') is obtained from ethyl 3'-chlorobenzoylacetate and 2-amino-5-picoline. Characteristics: prisms; mp 175-176 C.; 1 H NMR (CDCl3) delta 8.89 (s, 1 H, H-6), 8.13 (s, 1 H, H-2'), 7.92 (td, J=7.0, 1.0 Hz, 1 H, H-6'), 7.69 (d, J=9.0 Hz, 1 H, H-9), 7.64 (dd, J=9.0, 1.5 Hz, 1 H, H-8), 7.45 (m, 2 H, H2 -4', 5') 6.86 (s, 1 H, H-3), 2.46 (s, 3 H, CH3 -7). MS m/z 270 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With amberlite IRA-400; In tetrahydrofuran; ethanol; at 45℃; for 7h; | 141.6 g of diethyl carbonate was dissolved in 1000 mL of 1:1 ethanol-tetrahydrofuran (THF), and 12.4 g of catalyst 1 Amberlite IRA-400 was added under stirring.Warming up to 45 C,154.5 g of m-chloroacetophenone was dissolved in 1000 mL of the above-mentioned ethanol-THF mixed solvent, and the addition was completed within 1 h, and stirring was continued for 6 hours.Filter and recycle Amberlite IRA-400,Amberlite IRA-400 was washed 3 times with the above ethanol-THF mixed solvent.The filtrate is combined,Evaporate most of the solvent,Add 1500 mL of water with stirring.CH2Cl2 extraction,Wash with saturated saline until neutral,Dry over anhydrous MgSO4,filter,Evaporate the solvent,Distilled under reduced pressure to give a colorless oily liquid ethyl 3-(3-chlorophenyl)propanoate-3-one 204 g, yield 90%; |
In diethyl ether; mineral oil; | Synthesis of 3-(3-Chloro-phenyl)-3-oxo-propionic acid ethyl ester STR56 This synthesis was carried out as described in Chem. Pharm. Bull., 1987;35(9):3909-3913. Sodium hydride (60% dispersion in mineral oil; 0.05 mol) was suspended in diethyl ether (50 mL), and diethyl carbonate (118.1 g/mol; 0.010 mol) was added. A solution of 3-chloroacetophenone (154.6 g/mol; 0.02 mol) in diethyl ether (20 mL) was then added dropwise. The reaction mixture was refluxed for 7 hours and stirred at room temperature overnight. The reaction mixture was poured into water (40 mL), acidified to pH 2 with 2N HCl, and extracted with ethyl acetate (3 times: 50 mL). The ethyl acetate solution was dried over MgSO4, filtered, and concentrated to give 3.31 g (73% yield) of crude product. Purification was carried out by flash chromatography (silica gel: 145 g; eluent:chloroform) to give 0.51 g (11% yield) of the desired product. MS: APCI: M+1: 227.1 (M: 226). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ethyl m-chlorobenzoylacetate (79s) 1H NMR d: 1.26 (t, J=6.9 Hz, 3 H), 3.91 (s, 2 H), 4.22 (t, J=6.9 Hz, 2 H), 7.36-7.84 (m, 3 H), 7.93 (s, 1 H). MS (CI/NH4): m/z 244 (C11H1135ClO3, M++NH4, base), 227 (C11H1135ClO3, M++1). | ||
General procedure: Add NaH (1.12 g, 28 mmol) to a three-necked flask.Diethyl carbonate (3.4 mL, 28 mmol)And 10 mL of anhydrous toluene, reflux reaction for 1 h. Cool to room temperature,A solution of acetylcyclohexane (1.4 mL, 10 mmol) in toluene (5 mL) was added dropwise.After the completion of the dropwise addition, the reflux reaction was continued for 1 hour. After the reaction is completed, the reaction solution is cooled.Add acetic acid dropwise until no bubbles are formed, generating a large amount of solids.Add ice water to dissolve all the solids. Toluene is distilled off under reduced pressure.The aqueous phase was extracted with EtOAc (30 mL×3).Washed with water, washed with saturated NaCl, dried with anhydrous Na2SO4.Column chromatography separation (petroleum ether: EtOAc = 25:1)A yellow oily liquid was obtained, 1.11 g.Yield: 56%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5-(3-Chloro-phenyl)-2-methyl-oxazole-4-carboxylic acid:; Prepared starting from 3-chloro-benzoic acid following sequentially general procedure K, F, G and E. LC-MS-conditions 02: tR = 0.87 min; [M+H]+ = 238.06.; General procedure K: Claisen condensation:; O O OR^OH R1 O-*A) In a flame dried round-bottomed flask equipped with a magnetic stir bar and under an inert atmosphere (N2), a 1.3M solution of the acid derivative (1.0 eq.) in 1 ,2-dichloroethane was treated at rt with a few drops of DMF followed by oxalyl chloride (1.3 eq.). The reaction mixture was stirred for 3 h at rt followed by 20 min at 80 0C. The solvent was removed under reduced pressure.; B) In a flame dried round-bottomed flask equipped with a magnetic stir bar and under an inert atmosphere (N2), a 0.83M solution of potassium malonic acid monoethyl ester (2 eq.) in acetonitrile was treated at 10 0C with magnesium chloride (2.5 eq.) and the suspension was stirred at 10 0C for 30 min and at rt for 3 h. The reaction mixture was cooled to 0 0C and treated dropwise over 15 min with the solution of the acid chloride prepared under A, followed by Et3N (2 eq.). The resulting suspension was stirred at rt for 20 h. The solvent was removed under reduced pressure and the residue was striped with toluene. The residue was taken in toluene (1.5 ml. per mmol of potassium malonic acid monoethyl ester) and treated at 10 0C with the same amount of 4M HCI as of toluene. The organic layer was washed twice with 4M HCI, water, dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The residue was purified by FC to afford the desired derivative. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In ethanol; water; | 6b. Synthesis of 4-(3-Chloro-phenyl)-7-hydroxy-chromen-2-one STR57 This synthesis was carried out as described in Chem. Pharm. Bull., 1987;35(9):3909-3913. The product from Step 6a <strong>[33167-21-4]3-(3-chloro-phenyl)-3-oxo-propionic acid ethyl ester</strong> (226 g/mol; 0.0023 mol) was dissolved in ethanol (20 mL). Resorcinol (110.1 g/mol; 0.0023 mol) was added, and the solution was cooled to 0 C. The solution was saturated with HCl gas, and stirred for 1 hour at 0 C., and for 3 days at room temperature, under a nitrogen atmosphere. The reaction mixture was poured in water (25 mL) and the solution extracted with ethyl acetate (3 times: 50 mL). The ethyl acetate solution was dried over MgSO4, filtered, and concentrated to give 0.69 g (quantitative yield) of crude product. Purification was carried out by flash chromatography (silica gel: 45 g; eluent: 1:1/ethyl acetate:hexanes) to give 0.42 g (67% yield) of the desired product. MS: APCI: M+1: 273.0 (M: 272). |
31% | With sulfuric acid; at 0 - 20℃; for 2h; | General procedure: The title compounds were prepared as previously described [4] with slight modifications. To a stirred solution of the appropriate ethylbenzoylacetate (14a-h) (1mmol), resorcinol (15) or 2-methylresorcinol (16) (1mmol) and 96% sulfuric acid (1.5ml) was added dropwise at 0C. The resulting mixture was stirred for different reaction times at room temperature and monitored by TLC until completion. The reaction was quenched with ice and extracted with EtOAc (3×10mL). The organic phase was dried with Na2SO4 and concentrated until dryness under reduced pressure. The residue was purified by crystallization with suitable solvent to afford the desired compounds 17a-h and 18a-h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; acetic acid; In ethanol; for 5h;Reflux; | General procedure: Catalytic amounts of piperidine and acetic acid were added to a mixture of 2-hydroxy-1-naphthaldehyde (2.15 g, 12.5 mmol) and 3-oxo-3-thiophen-3-yl-propionic acid ethyl ester (2.97 g, 14.9 mmol) in dry ethanol (66 mL). The solution was then stirred at reflux temperature for 5 h. After completion of the reaction, the cooled suspension was filtered off and the crude yellow solid was purified by recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | In acetic acid; at 110℃; for 20h; | A suspension of N-(5-amino-3-oxo-2,3-dihydro-1 H-pyrazol-4-yl)acetamide (2.87 g, 18.38 mmol) and <strong>[33167-21-4]ethyl 3-(3-chlorophenyl)-3-oxopropanoate</strong> (5 g, 22.06 mmol, 1.2 equiv.) in acetic acid (50 ml) is stirred at 110 0C for 20 h. The mixture is allowed to cool to rt and water is added. The resulting suspension is filtered off, washed with water/EtOH and with ether, and air-dried to afford 2.76 g (47%) of a light brown solid. LC-MS m/z 317 (M-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | In acetic acid; at 100℃; for 48h; | Ethyl 5-amino-3-oxo-2,3-dihydro-1 H-pyrazole-4-carboxylate (12.25 g, 71.5 mmol) is dispersed in acetic acid (70 ml) and <strong>[33167-21-4]ethyl 3-(3-chlorophenyl)-3-oxopropanoate</strong> (19.46 g, 86 mmol, 1.2 equiv.) is added. The mixture is heated to 100 0C for 2 days. The resulting suspension is filtered off and washed with diisopropyl ether to give an off-white solid. The solid is stirred with acetic acid (30 ml) at 100 0C for 5 min. Hot filtration affords 6.7 g (28%) of the product as an off-white solid.LC-MS m/z 332/334 (M-H, Cl isotope pattern); 1H-NMR (400 MHz1 DMSO-d6): delta (ppm) 1.32 (3H1 t), 4.26 (2H, q), 6.27 (1 H, s), 7.59 (1 H1 t), 7.65-7.69 (1 H1 m), 7.70-7.75 (1 H1 m), 7.83 (1 H1 1), 11.40 (1 H, s), 11.66 (1 H1 br s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate 9.1 : 2-{3-Chloro-benzoyl)-4-oxo-4-phenyl-butyric acid ethyl ester; 3-(3-Chloro-phenyl)-3-oxo-propionic acid ethyl ester (500 mg, 2.2 mmol) is dissolved in THF (20 ml). The solution is cooled to 00C and NaH (60 % oil dispersion , 105 mg, 2.2 mmol) is added. The reaction mixture is allowed to warm to rt and stirred for 1 h. A solution of 2-bromo-1-phenyl-ethanone (440 mg, 2,2 mmol) in THF (10 ml) is added at rt and sirring continued for 1 h , while a yellow precipitate forms. The reaction is quenched by addition of aq. NH4CI (1N) and EtOAc. The organic layer is separated , dried over Na2SO4, concentrated and dried under high vacuum to give the title compound as a yellow solid. ES-MS: M+ = 345.0; 1HNMR (CDCI3) delta 8.07 (s, 1H), 8.03-8.00 (m, 3H), 7.59 (d, 2H), 7.47-7.44 (m, 3H), 5.04 (dd, 1 H), 4.17 (q, 2H), 3.87 (dd, 1H)1 3.73 (dd, 1 H), 1.18 (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | Preparation of (E)-7-bromo-4-(3-chlorophenyl)-1H-benzo[b][1,4]diazepin-2(3H)-one (compound 185) From <strong>[33167-21-4]ethyl 3-(3-chlorophenyl)-3-oxopropanoate</strong>, a brown solid (23%) is obtained. ESI+MS: calcd for C15H10BrClN2O: 347.97; found: 348.8 (MH+) |
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