Structure of 52273-77-5
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CAS No. : | 52273-77-5 |
Formula : | C8H11NO |
M.W : | 137.18 |
SMILES Code : | NC1=CC=CC(CCO)=C1 |
MDL No. : | MFCD02683213 |
Boiling Point : | No data available |
InChI Key : | FNUKLSVGSFFSLI-UHFFFAOYSA-N |
Pubchem ID : | 14938987 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 41.78 |
TPSA ? Topological Polar Surface Area: Calculated from |
46.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.34 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.61 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.81 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.21 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.28 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.05 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.39 |
Solubility | 5.63 mg/ml ; 0.041 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.16 |
Solubility | 9.59 mg/ml ; 0.0699 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.24 |
Solubility | 0.784 mg/ml ; 0.00571 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.7 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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 10 % Pd/C; In tetrahydrofuran;Cooling with ice; Inert atmosphere; | In tetrahydrofuran (2 mL) solution of 2-(3-nitrophenyl) ethanol (200 mg, 1.20 mmol), 10% palladium carbon (M) Dry (20 mg) was added under ice-cooling and argon gas atmosphere. Hydrogen gas replaced, after degassing the inside of a reaction container under decompression. Reaction mixture was violently stirred for 90 minutes under a room temperature and hydrogen gas atmosphere (balloon). After washing the insoluble matter by filtration and THF and being crowded, concentration hardening by drying was doubled and carried out, and the filtrate and the washing liquid obtained the compound (an opalescence solid, 165 mg, and 1.20 mmol, quantitive) of the mark. |
99% | With hydrogen;palladium 10% on activated carbon; In methanol; under 2327.23 Torr; | Step A: 2-(3-Aminophenyl)ethanol Into a pressure bottle were added <strong>[52022-77-2]2-(3-nitrophenyl)ethanol</strong> (3.0 g, 18 mmol) and methanol (100 mL) and 10% palladium on carbon (0.1 g, 0.08 mmol). The reaction mixture was hydrogenated at 45 psi overnight. The resultant mixture was filtered and concentrated to provide the desired product (2.44 g, 99%) as a white solid. LCMS for C8H12NO (M+H)+: m/z=138.1. |
98% | With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 1.5h; | (28A) 2-(3-Aminophenyl)ethanol 3-Nitrophenethyl alcohol (5.80 g, 34.7 mmol) was dissolved in ethanol (80 mL), and 10% palladium on carbon (0.90 g) was added thereto, and then, the resulting mixture was stirred under a hydrogen atmosphere at room temperature for 1.5 hours. The reaction solution was filtered through a Celite filter, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate = 80:20 to 40:60 (v/v)), whereby the target compound was obtained as a light yellow solid (4.65 g, yield: 98%). 1H NMR(CDCl3, 400MHz): delta2.77(2H, t, J=6.5Hz), 3.45-3.78(2H, brs), 3.82(2H, t, J=6.5Hz), 6.53-6.58(2H, m), 6.62(1H, d, J=7.4Hz), 7.06-7.13(1H, m). |
95% | With hydrogen;palladium 10% on activated carbon; In ethanol; for 18h; | A mixture of nitro phenethyl alcohol (8.Og, 0.047mol) and 10% Pd/C (0.6g) in ethanol (100ml) was stirred under a hydrogen atmosphere (balloon pressure) for 18 h. The reaction mixture was filtered through a pad of celite and the Pd/C catalyst removed. The filtrate was concentrated under reduced pressure to yield a light brown solid 6.1 g (95% yield). LCMS purity 98%, m/z 138 [M+H]+. |
93% | With hydrogen;5%-palladium/activated carbon; In ethyl acetate; at 20℃; | 3-Nitrophenethyl alcohol (4.8g, 28. 7mmol) was dissolved in 117ml ethyl acetate. A small amount of 5% palladium on activated carbon was added. The reaction was stirred overnight at room temperature under hydrogen atmosphere. According to thin layer chromatography all the starting material was consumed. The mixture was filtered through CELITE and the solvent was evaporated to give 3.7g (93% yield) of the desired product. 1HNMR (400MHZ, CDC13) : 2.76 (t, 2H), 3.81 (t, 2H), 6.52-6. 57 (M, 2H), 6.62 (d, 1H), 7.06- 7.11 (M, 1H) |
89% | With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; | Into a 250-mi. round-bottom flask, was placed a solution of <strong>[52022-77-2]2-(3-nitrophenyl)ethan-1-ol</strong>g, 6.58 mmol, 1.00 equiv) in ethanol (100 mL). 10% Palladium on carbon (500 mg) wasadded to the reaction mixture. The resulting solution was stirred overnight at room temperature under hydrogen atmosphere. The solids were filtered out. The filtrate was concentrated under vacuum to yield 800 mg (89%) of 2-(3-aminophenyl)ethan-1-ol as a brown oil. |
89% | With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; | Into a 250-mL round-bottom flask, was placed a solution of 2-(3-nitrophenyl)ethan-l-ol (1.1 g, 6.58 mmol, 1.00 equiv) in ethanol (100 mL). 10% Palladium on carbon (500 mg) was added to the reaction mixture. The resulting solution was stirred overnight at room temperature under hydrogen atmosphere. The solids were filtered out. The filtrate was concentrated under vacuum to yield 800 mg (89%) of 2-(3-aminophenyl)ethan-l-ol as a brown oil. |
54% | With palladium 10% on activated carbon; ammonium formate; In methanol; at 20℃; for 1h; | Example 129 2, 4-DIMETHYL-N- (4- ((1 R, 2S)-2- [4- (2-METHYL-5-QUINOLINYL)-1- PIPERAZINYL] CYCLOPROPYL} PHENYL)-1, 3-THIAZOLE-5-CARBOXAMIDE DIHYDROCHLORIDE and 2, 4-DIMETHYL-N-(4-{(1 R, 2S)-2- [4- (2-METHYL-5-QUINOLINYL)-1- PIPERAZINYL] CYCLOPROPYL} PHENYL)-1, 3-THIAZOLE-5-CARBOXAMIDE DIHYDROCHLORIDE (E129) 2- (3-Aminophenyl) ethanol; 2- (3-Nitrophenyl) ethanol (836mg, 5. 00mmol) and Pd (10% on charcoal, 200mg) were suspended in dry methanol (10 mL). After the addition of ammonium formate (1.450g, 23MMOL) a slightly exothermic and effervescent reaction was observed. After stirring for 1h at room temperature the mixture was filtered over celite. The filtrate was evaporated and the residue dissolved in ethyl acetate. After washing with saturated aqueous sodium hydrogencarboante solution, water and brine the organic layer was dried (magnesium sulfate) and the solvent removed under reduced pressure affording the title compound in 54% yield (373mg) as a white solid. MS; (ES) m/z: 138 [MH+]. CGHNNO requires 137. 1H-NMR (300 MHz, d6-DMSO) B (ppm): 6.80 (t, 1H), 6.25-6. 35 (m, 3H), 4.85 (s, 2H), 4.50 (t, 1 H), 3.45 (dt, 2H), 2.45 (t, 2H). |
With tin(ll) chloride; In ethanol; | 2- (3-NITROPHENYL) ETHAN-L-OL (1.0 Eq, 1.200 mmol, 0.200 g) was reduced on SNC12. 2H20 (6.0 Eq, 7.200 mmol, 1.625 g) and EtOH (20 mL). The solvent was removed and the product was purified by flash chromatography on silica gel: DICHLOROMETHANE/MEOH (95/5). 2- (3-AMINOPHENYL) ETHAN-L-OL (1.0 Eq, 0. 437MMOL, 0.060 g) was mixed with 2-chloroethyl isocyanate (1.2 Eq, 0.524 mmol, 0.055 g), in dichloromethane (15 mL) as described in Example 31. The solvent was removed and the product was purified by flash chromatography on silica gel: ETHER/HEXANE (90/10). Yield = 20% H NMR (Acetone-d6) 8 : 8.08 (brs, NH, 1H), 7.33 (m, Ar, 2H), 7.13 (m, Ar, 1H), 6.82 (d, Ar, 1H, J = 7.44), 6.15 (brs, NH, 1H), 3.69 (m, 4H), 3.53 (m, 2H), 2.93 (s, OH, 1H), 2.74 (t, 2H, J = 7.02). 13C NMR (Acetone-d6) B : 177.3, 155.9, 140.9, 129.2, 123.1, 119.5, 116.7, 63.7, 44. 8, 42.4, 40.3. | |
With tin(ll) chloride; In ethanol; water; | 2- (3-NITROPHENYL) ETHAN-L-OL (1.0 Eq, 1.200 mmol, 0.200 g) was reduced on SNCL2. 2H20 (6.0 Eq, 7.200 mmol, 1.625 g) and EtOH (20 mL). The solvent was removed and the product was purified by flash chromatography on silica gel: dichloromethane/MeOH (95/5). 2- (3-AMINOPHENYL) ETHAN-L-OL (1.0 Eq, 0.437mmol, 0.060 g) was mixed with 2-chloroethyl isocyanate (1.2 Eq, 0.524 mmol, 0.055 g), in dichloromethane (15 mL) as described in Example 31. The solvent was removed and the product was purified by flash chromatography on silica gel: Ether/Hexane (90/10). Yield = 20% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); for 14h; | N- [3- (2-HYDROXYETHYL) PHENYL]-2, 4-DIMETHYL-1, 3-THIAZOLE-5-CARBOXAMIDE; 2- (3-Aminophenyl) ethanol (1.202 g, 8.76 MMOL) was added to a solution of 2, 4-dimethyl- 1, 3-thiazole-5-carboxylic acid (1.652 g, 10.51 MMOL), 1- (3-DIMETHYLAMINOPROPYL)-3- ethylcarbodiimide hydrochloride (2.015 g, 10.51 MMOL) and 1-hydroxybenzotriazole (1.420 g, 10.51 MMOL) in dry DMF (20 mL). The mixture was stirred for 14h then the DMF was removed under reduced pressure and the residue was partitioned between DCM and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel, eluting with ethyl acetate-cyclohexane (1: 1 to 1: 0) affording the title compound in 73% yield (1.772 g). MS; (ES) m/z: 277 [MH+]. C14H16N202S requires 276. 1H-NMR (300 MHz, D6-DMSO) S (ppm): 9.95 (s, 1H), 7.40-7. 50 (m, 2H), 7.19 (t, 1H), 6.92 (d, 1 H), 4.60 (t, 1 H), 5.57 (dd, 2H), 2.66 (t, 2H), 2.61 (s, 3H), 2.49 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In ethanol; water; | a 3-Aminophenethyl alcohol To a solution of <strong>[52022-77-2]3-nitrophenethyl alcohol</strong> (5.13 g, 30.7 mmol), in ethanol (100 ml), was added a slurry of 10% Pd--C (0.5 g), in water (4 ml), and the mixture hydrogenated in a Parr flask, at 45 psi for 0.75 h. The catalyst was removed by filtration and the solvent evaporated to give 3-aminophenethyl alcohol (4.2 g, 100%), mp 61-64 C., delta (360 MHz, CDCl3) 2.77 (2H, t, J=6.7 Hz, CH2), 3.80 (2H, t, J=6.7 Hz, CH2), 6.55-6.63 (3H, m, Ar--H), 7.08 (1H, dd, J=7.6 and 8.06 Hz, Ar--H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; | 0.75 g of 5% palladinized charcoal is added to a solution of 15 g of <strong>[52022-77-2]2-(3-nitrophenyl)ethanol</strong> in 250 cm3 of ethanol. The suspension is stirred for 2 hours at a temperature in the vicinity of 25 C. under a hydrogen atmosphere (130 kPa). The catalyst is separated by filtration and the filtrate is concentrated to dryness under reduced pressure at 45 C. 12 g of 2-(3-aminophenyl)ethanol thus obtained in the form of an orange oil, used as it is in subsequent syntheses. |
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