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CAS No. : | 1929-29-9 | MDL No. : | MFCD00002777 |
Formula : | C10H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FIUFLISGGHNPSM-UHFFFAOYSA-N |
M.W : | 180.20 | Pubchem ID : | 95750 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 49.29 |
TPSA : | 46.53 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.05 cm/s |
Log Po/w (iLOGP) : | 1.69 |
Log Po/w (XLOGP3) : | 1.9 |
Log Po/w (WLOGP) : | 1.71 |
Log Po/w (MLOGP) : | 1.67 |
Log Po/w (SILICOS-IT) : | 1.91 |
Consensus Log Po/w : | 1.78 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.23 |
Solubility : | 1.06 mg/ml ; 0.00586 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.5 |
Solubility : | 0.57 mg/ml ; 0.00316 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.71 |
Solubility : | 0.354 mg/ml ; 0.00196 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.12 |
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 |
---|---|---|
100% | With trifluorormethanesulfonic acid In dichloromethane at 0 - 80℃; for 1 h; High pressure; Inert atmosphere; Green chemistry | General procedure: Trifluoromethane sulfonic acid (3 eq.) was gently added to a cooled (0 °C) solution of a 3-Phenylpropionic acid (0.5 mmol) in dry CH2Cl2 (1.0 mL) in a 12 mL Q-tube™ pressure tube, furnished by QLabtech. The temperature was raised to room temperature. A Teflon septum was placed on the top of the tube and the appropriate cap and pressure adapter were used. The mixture was heated in an oil bath at 80 °C. The reaction was monitored by TLC and GC/MS until the reactant disappeared. The mixture was poured into ice and extracted three times with CH2Cl2. The organic phase collected was dried on Na2SO4, filtered and concentrated under vacuum. The desired pure product was separated from the crude by flash chromatography. |
88% | With thionyl chloride In dichloromethane | (a) To a solution of 3-(4-methoxyphenyl)propionic acid (50.34 g, 0.279 mol) in 500 ml of methylene chloride cooled to 0° C. was added slowly at 0° C. 30.5 ml (0.418 mol) of thionyl chloride, the mixture was stirred 10 h, at room temperature and the solvent was removed in vacuo. The residue was dissolved in 1000 ml of methylene chloride, cooled to 0° C., and 40.92 g (0.306 mol) of aluminum chloride was added in small portions and the resulting mixture was sitrred at room temperature for 1 h. The above mixture was poured onto ice, the resulting mixture was filtered through celite, and the aqueous layer was extracted with methylene chloride (2*200 ml). The combined organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was extracted with hexane to afford 40 g (88percent) of 6-methoxy-1-indanone. |
88% | With thionyl chloride In dichloromethane | (a) To a solution of 3-(4-methoxyphenyl)propionic acid (50.34 g, 0,279 mol) in 500 mL of methylene chloride cooled to 0° C. was added slowly at 0° C. 30.5 mL (0.418 mol) of thionyl chloride, the mixture was stirred 10 h at room temperature and the solvent was removed in vacuo. The residue was dissolved in 1000 mL of methylene chloride, cooled to 0° C., and 40.92 g (0.306 mol) of aluminum chloride was added in small portions and the resulting mixture was stirred at room temperature for 1 h. The above mixture was poured onto ice, the resulting mixture was filtered through celite, and the aqueous layer was extracted with methylene chloride (2*200 mL). The combined organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was extracted with hexane to afford 40 g (88percent) of 6-methoxy-1-indanone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.2% | With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; for 5 h; | To a solution of 3-(4-methoxyphenyl)acrylic acid (15, 14.7 mmol) in THF (50 mL) was added a catalytic amount of 10percent palladium on activated carbon to carry out hydrogenation, followed by stirring for 5 h at room temperature. The mixture was filtered, and the filtrate was concentrated in vacuo to give a white solid with a yield of 95.2percent, mp 102-103 °C |
95.2% | With palladium 10% on activated carbon In tetrahydrofuran; methanol at 20℃; for 5 h; | Plus p-methoxycinnamic acid(11a, 14.7 mmol), tetrahydrofuran (50 mL),Methanol (20 mL),Catalytic amount of 10percent Pd / C, hydrogen, The reaction was stirred at room temperature for 5 h. The reaction was terminated and the solid was filtered off. The solution was concentrated to dryness under reduced pressure to give a white solid, 95.2percent yield, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.1% | With hydrogenchloride; zinc amalgam In tetrahydrofuran; water | General procedure: A mixture of zinc powder (25 g, 0.384 mol) and mercuric chloride(3.1 g, 0.0114 mol) was suspended in 100 mL of water in a 250 mLbeaker. The mixture was treated with 50 mL of con. HCl slowly dropwise and after completion of addition, the stirring was continued for15 min. The mixture was decanted to separate the solution and theremaining Zn-Hg amalgam was used for reduction. To a mixture of substituted cinnamic acid (1a-e, 0.134 mol), THF(150 mL) and 5 N HCl (100 mL) was added above freshly prepared Zn-Hg amalgam slowly portion wise. An additional 5 N HCl (50 mL) addedand the stirring continued for 2 h. After completion of reaction, asmonitored by TLC hexane/ethyl acetate (8:2), the reaction mixture waspoured into water (200 mL) and extracted with chloroform(2×400 mL), The organic layer was washed with brine solution, driedover Na2SO4 and concentrated. The crude residue was subjected to column chromatography on silica gel using hexane/ethyl acetate mixturesas eluents. The fractions were monitored using TLC and purecompound was obtained from the fractions eluted with ethyl acetate inhexane, 5percent/95percent (v/v). These fractions were combined and concentratedto obtained 3-(substituted-phenyl)-propionic acids (2a-e) asoily compounds with yields of 79–86percent. |
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