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CAS No. : | 19819-98-8 | MDL No. : | MFCD00044241 |
Formula : | C9H12O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RUGISKODRCWQNE-UHFFFAOYSA-N |
M.W : | 136.19 | Pubchem ID : | 88267 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.34 |
TPSA : | 20.23 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) : | -5.81 cm/s |
Log Po/w (iLOGP) : | 1.91 |
Log Po/w (XLOGP3) : | 1.86 |
Log Po/w (WLOGP) : | 1.53 |
Log Po/w (MLOGP) : | 2.19 |
Log Po/w (SILICOS-IT) : | 2.48 |
Consensus Log Po/w : | 1.99 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.17 |
Solubility : | 0.925 mg/ml ; 0.00679 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.91 |
Solubility : | 1.69 mg/ml ; 0.0124 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.99 |
Solubility : | 0.14 mg/ml ; 0.00103 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-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 |
---|---|---|
75% | With lithium aluminium tetrahydride; In diethyl ether; for 3h;Reflux; | Preparation of 2-(o-tolyl)ethanol (S1) A solution of o-tolylacetic acid 23 (330 mg, 2.20 mmol) in dry ether (5 mL) was slowly added to a stirred mixture of LiAlH4 (180 mg, 4.7 mmol) in dry ether (5 mL) in a 100 mL round-bottom flask. Once gas evolution had subsided, the mixture was refluxed for 3 h. The mixture was quenched by careful addition of 0.2 mL of water, 0.2 mL of 15% NaOH aqueous solution, and 1.2 mL of water. The insoluble salts were removed by filtration, and the organic layer was washed with brine and dried over anhydrous MgSO4. The ether was removed on a rotary evaporator with an ambient temperature bath to leave 2-(o-tolyl) ethanol (S1) (Sakai, N., et al., Eur. J. Org. Chem. 2011, 3178-3183) as a light yellow liquid (219 mg, 1.61 mmol, 75%). 1H NMR (500 MHz, CDCl3) delta 7.22-7.10 (m, 4H), 3.85 (t, J=6.9 Hz, 2H, CH2OH), 2.90 (t, J=6.8 Hz, 2H, CH2Ar), 2.34 (s, 3H, CH3), and 1.42 (br s, 1H, OH). |
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 4.5h;Reflux; | General procedure: To a mixture of LiAlH4 (15 mmol) in anhydrous THF (25 mL) in an ice-bath was added dropwise a solution of phenylacetic acids (15 mmol) in THF (8 mL). This mixture was stirred at room temperature for 30 min, and then heated to reflux for 4 h. After it was cooled to room temperature, water (0.5 mL) was added, and then NaOH (15%, 0.5 mL) and water (1.5 mL) were added in sequence. After stirring for another 30 min, the mixture was filtered, dried over anhydrous Na2SO4 and concentrated to give crude products. Pure phenylethyl alcohols were obtained in 50-85% yield by column chromatography. Alternative method: To a solution of phenylacetic acids (15 mmol) in MeOH (30 mL) was added SOCl2 (30 mmol). This mixture was heated to reflux for 3 h before evaporation. The residue was dissolved in DCM (30 mL), washed with aqueous NaHCO3, water and brine, dried over anhydrous Na2SO4, and concentrated to give 100% yield of crude methyl phenylacetates which were used to next step without further purification. To a solution of the methyl phenylacetates in THF (30 mL) was added NaBH4 (60 mmol). When the mixture was heated to gently reflux, MeOH (1.0 mL) was added dropwise from a syringe over 5 min. After refluxing for another 6 h, the mixture was cooled to room temperature and poured into 30 mL ice water, and extracted with EtOAc (30 mL × 2). The combined organic phase was washed with brine, dried over anhydrous Na2SO4, and concentrated to give crude products. Pure phenylethyl alcohols were obtained in 70-85% yield by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dipyridine chromium trioxide; In dichloromethane; at 25℃; | The phenylacetaldehydes 6a-n were prepared by oxidation of the corresponding phenylethyl alcohols using dipyridine chromium (VI) oxide (Collin's reagent) in dry dichloromethane at 25 C. according to reported procedures. | |
With Dess-Martin periodane; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: The alcohol (1.0 eq) was added to a suspension of Dess-Martin periodinane (1.2 eq) in CH2Cl2(100 mM) under an argon atmosphere at room temperature. The mixture was allowed to stir for0.5 - 20 hours, while consumption of starting material was monitored by TLC. After the reactionwas complete, 1M Na2S2O3 (equal volume to CH2Cl2) was added. After stirring for 15 minutes,the phases were separated and the aqueous phase was extracted with CH2Cl2 twice. Thecombined organic layers were washed with 5% NaHCO3 and brine, and dried over Na2SO4. Thesolvent was evaporated under reduced pressure and the residue was purified by columnchromatography to afford analytically pure aldehydes.b) alcohol precursors for aldehydes 13, 14, 20 (solid alcohols)The alcohol (1.0 eq) was dissolved in CH2Cl2 (200 mM) and the solution was added to asuspension of Dess-Martin periodinane (1.2 eq) in CH2Cl2 (200 mM) under an argon atmosphereat room temperature. The mixture was allowed to stir for 0.5 - 20 hours (TLC monitoring). Then,Et2O (equal volume to CH2Cl2), 1M Na2S2O3 and saturated NaHCO3 (both equal volume toCH2Cl2) were added. After stirring for 15 minutes, the phases were separated and the aqueousphase was extracted with Et2O twice. The combined organic layers were washed with sat.NaHCO3 and brine, and dried over Na2SO4. The solvent was evaporated under reduced pressureand the residue was purified by column chromatography to afford analytically pure aldehydes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Example 305: 2-[1-(4-Chlorophenylsulfonyl)-3-(2-methylphenyl)propyl]-1,4-difluorobenzene In a similar manner to Example 304 except for the use of <strong>[19819-98-8]2-(2-methylphenyl)ethanol</strong> (89.0 mul, 0.661 mmol), the title compound (108 mg, 0.257 mmol, 78%) was obtained as colorless plate crystals.1H-NMR (400 MHz, CDCl3) delta: 2.18(3H,s), 2.29-2.39(1H,m), 2.46-2.62(2H,m), 2.67-2.75(1H,m), 4.53(1H,dd,J=11.1,2.6Hz), 6.86(1H,td,J=9.0,4.4Hz), 6.96-7.12(5H,m), 7.28(1H,ddd,J=8.7, 5.4,3.2Hz), 7.37(2H,d,J=8.6Hz), 7.51(2H,d,J=8.6Hz). IR (ATR) cm-1: 3091, 2946, 1583, 1573, 1496, 1425, 1392, 1311, 1276, 1213, 1151, 1143, 1083, 1010. mp: 105-106C. MS m/z: 421 (M++H).Anal. calcd for C22H19ClF2O2S: C, 62.78; H, 4.55; Cl, 8.42; F, 9.03; S, 7.62. Found: C, 62.48; H, 4.63; Cl, 8.52; F, 9.16; S, 7.75. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 18 - 25℃; | To a stirred solution of tert-butyl 4-([(5-chloro-2-hydroxybenzoyl)amino]methyl}benzoate (step 1 of the synthetic procedure of example 1-4, 0.21 g, 0.58 mmol), <strong>[19819-98-8]2-(2-methylphenyl)ethanol</strong> (0.16 g, 1.2 mmol) and triphenylphosphine (0.30 g, 1.2 mmol) in tetrahydrofuran (5 mL) was added di-tert-butyl azodicarboxylate (0.27 g, 1.2 mmol) at room temperature. After being stirred overnight, the reaction was quenched by the addition of sodium bicarbonate aqueous solution. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried (magnesium sulfate), and evaporated. The remaining residue was purified by flush column chromatography on silica gel eluding with hexane/ethyl acetate (5/1) to afford 0.21 g (76%) of the title compounds as a colorless oil: 1H-NMR (CDCl3) 8.20 (1H, d, J=2.8 Hz), 7.99 (1H, t, J=5.9 Hz), 7.91 (2H, d, J=8.2 Hz), 7.38 (1H, dd, J=8.7, 2.8 Hz), 7.25 (2H, d, J=8.2 Hz), 7.16-7.03 (4H, m), 6.93 (1H, d, J=8.7 Hz), 4.52 (2H, d, J=5.9 Hz), 4.34 (2H, t, J=6.8 Hz), 3.04 (2H, t, J=6.8 Hz), 2.25 (3H, s), 1.59 (9H, s); MS (ESI) m/z 480 (M+H)+. |
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; | To a stirred solution of tert-butyl 4-([(5-chloro-2- hydroxybenzoyl) amino]methyl}benzoate (step 1 of Example 1,0.21 g, 0.58 mmol), 2- (2-methylphenyl)ethanol g, 1.2 mmol) and triphenylphosphine (0.30 g, 1.2 mmol) in tetrahydrofuran (5 mL) was added di-tert-butyl azodicarboxylate (0.27 g, 1.2 mmol) at room temperature. After being stirred overnight, the reaction was quenched by the addition of sodium bicarbonate aqueous solution. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried (magnesium sulfate), and evaporated. The remaining residue was purified by flush column chromatography on silica gel-eluting with hexane/ethyl acetate (5/1) to afford 0.21 g (76%) of the title compounds as a colorless oil: ¹H-NMR (CDC13) No. 8.20 (1 H, d, J = 2.8 Hz), 7.99 (1 H, t, J = 5.9 Hz), 7.91 (2H, d, J = 8.2 Hz), 7.38 (1 H, dd, J = 8.7,2.8 Hz), 7.25 (2H, d, J = 8.2 Hz), 7.16-7.03 (4H, m), 6.93 (1 H, d, J = 8.7 Hz), 4.52 (2H, d, J = 5.9 Hz), 4.34 (2H, t, J = 6.8 Hz), 3.04 (2H, t, J = 6.8 Hz), 2.25 (3H, s), 1.59 (9H, s); MS (ESI) m/z 480 (M + H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; trifluoroacetic acid; In dichloromethane; toluene; | a 2-[2-(2-Methylphenyl)ethoxy]acetic acid The subtitle compound (8.91 g) was prepared according to the procedure in example 5 part a using <strong>[19819-98-8]2-(2-methylphenyl)ethanol</strong> (5.0 g), t-butylbromoacetate (5.47 ml), tetrabutylammoniumbromide (0.78 g), toluene (80 ml), 50% aqueous sodium hydroxide (40 ml), trifluoroacetic acid (20 ml) and dichloromethane (20 ml). 1 H nmr (360 MHz, CDC3); 2.34 (3H, s),2.97 (2H, t), 3.75 (2H, t), 4.13 (2H, S), 7.12-7.17 (4H, m) 8.14 (1H, brs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.76 g (43%) | In hexane; ethyl acetate; N,N-dimethyl-formamide; | EXAMPLE 5 2-Methylphenethyl sulfamate A mixture of 2.65 g (0.019 mole) of <strong>[19819-98-8]2-methylphenethyl alcohol</strong> in 10 ml DMF was added dropwise to a suspension of sodium hydride (1.1 g, 60% in oil; 0.08 mole) in 35 ml DMF at 0-5 C. The suspension was stirred for 20 min under argon after which sulfamoyl chloride (2.86 g, 0.02 mole) was added portion wise at 0-5 C. After stirring for 20 min the resultant suspension was poured into ice and extracted twice with Et2 O. The combined organic phases were washed with saturated brine, dried over potassium carbonate and concentrated in vacuo to a syrup which was purified by preparative HPLC with hexane/EtOAc (1:1, v/v) as the eluant to give 1.76 g (43%) of the title compound as a solid, mp 50-52 C. Elemental Analysis: Calculated for C9 H13 NO3 S: C, 50.22; H, 6.09; N, 6.51. Found: C, 50.40; H, 6.14; N, 6.43. |
Tags: 19819-98-8 synthesis path| 19819-98-8 SDS| 19819-98-8 COA| 19819-98-8 purity| 19819-98-8 application| 19819-98-8 NMR| 19819-98-8 COA| 19819-98-8 structure
[ 22436-06-2 ]
(S)-2-Methyl-3-phenylpropan-1-ol
Similarity: 0.92
[ 22436-06-2 ]
(S)-2-Methyl-3-phenylpropan-1-ol
Similarity: 0.92
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