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CAS No. : | 22927-13-5 | MDL No. : | MFCD02261766 |
Formula : | C9H10O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NTWBHJYRDKBGBR-UHFFFAOYSA-N |
M.W : | 134.18 | Pubchem ID : | 123406 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.6 |
TPSA : | 17.07 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) : | -5.21 cm/s |
Log Po/w (iLOGP) : | 1.84 |
Log Po/w (XLOGP3) : | 2.69 |
Log Po/w (WLOGP) : | 2.06 |
Log Po/w (MLOGP) : | 2.1 |
Log Po/w (SILICOS-IT) : | 2.79 |
Consensus Log Po/w : | 2.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.68 |
Solubility : | 0.281 mg/ml ; 0.0021 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.7 |
Solubility : | 0.267 mg/ml ; 0.00199 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.1 |
Solubility : | 0.106 mg/ml ; 0.000787 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
74% | With sodium tetrahydroborate; In ethanol; at 0 - 25℃; for 2h; | To a solution of <strong>[22927-13-5]2-ethylbenzaldehyde</strong> (200 mg, 1.49 mmol) in ethanol (4.0 mL) cooled at 0 C, NaBH4(11.27 mg, 0.30 mmol) was added. The mixture was stirred for 1 h at 0 C, then allowed to reach 25C and stirred for 1 h. Thereafter, NH4Cl was added, the solvent was evaporated, and the residuewas extracted with ethyl acetate (3 x 5 mL). The combined organic phases were dried overanhydrous Na2SO4, filtered and concentrated. The resulting residue was purified by flashchromatography on silica gel (1:50 methanol/dichloromethane) to afford 14x as a colorless oil (74%yield). 1H NMR (400 MHz, CDCl3): delta 7.32 - 7.30 (m, 1H), 7.21 - 7.15 (m, 3H), 4.67 (s, 2H), 2.66 (q, 2H,J = 7.6 Hz), 1.60 (br s, 1H), 1.19 (t, 3H, J = 7.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 20℃; for 2h; | The compound (29.6 mg) obtained in Example 1-5 was dissolved in methanol (0.3 ml), and the solution was added with <strong>[22927-13-5]2-ethylbenzaldehyde</strong> (14.9 mg) and stirred at room temperature for 2 hours. After completion of reaction, the solvent was distilled off, and the residue was dried in vacuum and re-dissolved in methanol (0.6 ml). The solution was ice-cooled, and sodium borohydride (10 mg) was added to the solution. The resultant solution was returned to room temperature and stirred for 60 minutes. After completion of reaction, the solvent was distilled off, and the residue was dissolved in chloroform. The resultant solution was washed with 0.5 mol/l sodium hydroxide and brine and dried with anhydrous sodium sulfate, and the solvent was distilledoff. The residuewas dissolved in chloroform (0.9 ml), and methanesulfonic acid (33 mul) and methanol (33 mul) were added under ice-cooling, followed by stirring at room temperature for 1.5 hours. After completion of reaction, the solvent was distilled off, and the residue was purified by silica gel column chromatography (chloroform/methanol/water = 7/3/0.5), to thereby obtain a methanesulfonate (24.4 mg) of the subject compound as a white solid. MS(FAB,Pos.):m/z=617[M+1]+1H-NMR(500MHz,DMSO-d6) : delta=1.13(3H,t,J=7.6Hz) ,1.52(3H,d,J=6.8Hz), 1.64-1.81(4H,m),2.35(9H,s),2.66(2H,q,J=7.6Hz),2.95-3.05(2H,m), 4.10 (2H,t,J=5.1Hz) ,4.30(2H,s) ,4.37(2H,brs) ,4.56-4.62(1H,m) ,5.7 2(1H,quint. ,J=6.8Hz) ,7.23-7.30(2H,m) ,7.36(1H,td,J=7.6,1.2Hz) ,7 .40 (1H,d,J=7.8Hz) ,7.45-7.65 (8H,m) ,7.83 (1H,d,J=8.3Hz) ,7.94 (1H,d ,J=7.8Hz) ,7.98(2H,d,J=8.1Hz) ,8.10(1H,d,J=8.3Hz) ,8.55(1H,d,J=7. 3Hz) ,8.64(2H,brs) ,8.73(1H,d,J=7.8Hz) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | 5-Bromo-<strong>[22927-13-5]2-ethyl-benzaldehyde</strong> (235)A stirred suspension of <strong>[22927-13-5]2-ethylbenzaldehyde</strong> (0.98 mL, 7.45 mmol) and AlCl3 (1.74 g, 13 mmol) in DCM (4.5 mL) at 0C is treated with a solution of Br2 (0.38 mL 7.45 mmol) in DCM (4.5 mL) dropwise over 6 h then stirred 16 h at RT. After this time, EPO <DP n="364"/>the reaction mixture is poured over ice-water (50 mL), the layers separated and the aqueous layer extracted with DCM (3 x 50 mL). The organic phases are combined and washed with 2M HCl (100 mL), aqueous NaHCO3 (100 mL) and brine (100 mL), dried over Na2SO4 then the solvents removed in vacuo. Purification by column chromatography (gradient elution - 100% heptane increasing to 10% EtOAc in heptane) gives the title compound. Yield: 925 mg (58%). LC/MS tr 1.55 min. MS(ES+) m/z mass ion not detected. | |
58% | With bromine;aluminum (III) chloride; In dichloromethane; at 0 - 20℃; for 22h; | 5-Bromo-2-ethyI-benzaldehyde (235)A stirred suspension of <strong>[22927-13-5]2-ethylbenzaldehyde</strong> (0.98 mL, 7.45 mmol) and AlCl3 (1.74 g, 13 mmol) in DCM (4.5 mL) at 0C was treated with a solution of Br2 (0.38 mL <n="255"/>7.45 mmol) in DCM (4.5 mL) dropwise over 6 h then stirred 16 h at RT. After this time, the reaction mixture was poured over ice-water (50 mL), the layers separated and the aqueous layer extracted with DCM (3 x 50 mL). The organic phases were combined and washed with 2M HCl (100 mL), aqueous NaHCO3 (100 mL) and brine (100 mL), dried over Na2SO4 then the solvents removed in vacuo. Purification by column chromatography (gradient elution - 100% heptane increasing to 10% EtOAc in heptane) gave the title compound. Yield: 925 mg (58%). LCyMS fr 1.55 min. MS(ES+) m/z mass ion not detected. |
58% | With aluminum (III) chloride; bromine; In dichloromethane; at 0 - 20℃; for 22h; | 5-Bromo-<strong>[22927-13-5]2-ethyl-benzaldehyde</strong> (235); A stirred suspension of <strong>[22927-13-5]2-ethylbenzaldehyde</strong> (0.98 mL, 7.45 mmol) and AlCl3 (1.74 g, 13 mmol) in DCM (4.5 mL) at 0C is treated with a solution OfBr2 (0.38 mL 7.45 mmol) in DCM (4.5 mL) dropwise over 6 h then stirred 16 h at RT. After this time, EPO <DP n="364"/>the reaction mixture is poured over ice-water (50 mL), the layers separated and the aqueous layer extracted with DCM (3 x 50 mL). The organic phases are combined and washed with 2M HCl (100 mL), aqueous NaHCO3 (100 mL) and brine (100 mL), dried over Na2SO4 then the solvents removed in vacuo. Purification by column chromatography (gradient elution - 100% heptane increasing to 10% EtOAc in heptane) gives the title compound. Yield: 925 mg (58%). LC/MS tr 1.55 min. MS(ES+) m/z mass ion not detected. |
58% | With aluminum (III) chloride; bromine; In dichloromethane; at 0 - 20℃; for 22h; | Synthesis of Compound 395; 5-Bromo-<strong>[22927-13-5]2-ethyl-benzaldehyde</strong> (235); A stirred suspension of <strong>[22927-13-5]2-ethylbenzaldehyde</strong> (0.98 mL, 7.45 mmol) and AlCl3 (1.74 g, 13 mmol) in DCM (4.5 mL) at 0C is treated with a solution Of Br2 (0.38 mL 7.45 mmol) in DCM (4.5 mL) dropwise over 6 h then stirred 16 h at RT. After this time, EPO <DP n="364"/>the reaction mixture is poured over ice-water (50 mL), the layers separated and the aqueous layer extracted with DCM (3 x 50 mL). The organic phases are combined and washed with 2M HCl (100 mL), aqueous NaHCO3 (100 mL) and brine (100 mL), dried over Na2SO4 then the solvents removed in vacuo. Purification by column chromatography (gradient elution - 100% heptane increasing to 10% EtOAc in heptane) gives the title compound. Yield: 925 mg (58%). LC/MS U 1 -55 min. MS(ES+) m/z mass ion not detected. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1-Ethyl-2-(2-nitroethyl)-benzene Dissolve 2-ethyl benzaldehyde (7 mL, 53.2 mmol), nitromethane (8.5 mL, 158 mmol), and ammonium acetate (1.6 g, 20.8 mmol) in acetic acid (40 mL) and heat to reflux under a nitrogen atmosphere for 17 hours. Cool to room temperature and concentrate. Dissolve in isopropyl alcohol (150 mL) and chloroform (750 mL) and add silica gel (108 g). To the resulting slurry, slowly add sodium borohydride (7.8 g, 206 mmol). Stir the mixture for 17 hours, filter, concentrate and purify (silica gel chromatography, eluding with 0:100 to 10:90 ethyl acetate:hexanes), to give the desired compound as an orange oil. 1H-NMR (400 MHz, CDCl3) delta 7.12-7.26 (m, 4H), 4.57 (t, J=8.0 Hz, 2H), 3.67 (t, J=8.0 Hz, 2H), 2.68 (q, J=8.0 Hz, 2H), 1.25 (t, J=7.2 Hz, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of 1-bromo-2-ethyl-benzene (5.00 g, 27.02 mmol), Mg (4.00 g, 0.16 mol) and a catalytic amount of 12 in THF was refluxed for 2 hours. After cooling the reaction mixture to 0 C., DMF (10.00 mL) was added and the mixture was stirred for 30 minutes. It was then quenched with 10% HCl and the resulting solution was extracted with Et2O (3×200 mL). The combined organic extracts were washed with H2O (2×200 mL), brine (1×200 mL), dried over MgSO4 and concentrated to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; In pyridine; for 3h;Heating / reflux; | To a solution of <strong>[22927-13-5]2-ethyl-benzaldehyde</strong> (18.40 g, 0.14 mol) and malonic acid (28.00 g, 0.27 mol) in pyridine was added 10.00 mL of piperidine and the resulting mixture was slowly refluxed for 3 hours. After cooling to room temperature, the reaction mixture was diluted with ice water, acidified to pH<1. The resulting solid was filtered, washed with water and dried under vacuum to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3-(2-Ethyl-phenyl)-acrylic acidxvii: To a solution of <strong>[22927-13-5]2-ethyl-benzaldehyde</strong> (18.40 g, 0.14 mol) and malonic acid (28.00 g, 0.27 mol) in pyridine was added 10.00 mL of piperidine and the resulting mixture was slowly refluxed for 3 hours. After cooling to room temperature, the reaction mixture was diluted with ice water, acidified to pH<1. The resulting solid was filtered, washed with water and dried under vacuum to give the title compound. |
Tags: 22927-13-5 synthesis path| 22927-13-5 SDS| 22927-13-5 COA| 22927-13-5 purity| 22927-13-5 application| 22927-13-5 NMR| 22927-13-5 COA| 22927-13-5 structure
[ 41828-13-1 ]
5,6,7,8-Tetrahydronaphthalene-1-carbaldehyde
Similarity: 0.93
[ 30084-91-4 ]
2,3-Dihydro-1H-indene-5-carbaldehyde
Similarity: 0.93
[ 41828-13-1 ]
5,6,7,8-Tetrahydronaphthalene-1-carbaldehyde
Similarity: 0.93
[ 30084-91-4 ]
2,3-Dihydro-1H-indene-5-carbaldehyde
Similarity: 0.93
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