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CAS No. : | 6995-79-5 | MDL No. : | MFCD00063612 |
Formula : | C6H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VKONPUDBRVKQLM-UHFFFAOYSA-N |
M.W : | 116.16 | Pubchem ID : | 11162 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 31.17 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.87 cm/s |
Log Po/w (iLOGP) : | 1.38 |
Log Po/w (XLOGP3) : | 0.19 |
Log Po/w (WLOGP) : | 0.28 |
Log Po/w (MLOGP) : | 0.21 |
Log Po/w (SILICOS-IT) : | 0.63 |
Consensus Log Po/w : | 0.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.68 |
Solubility : | 24.3 mg/ml ; 0.209 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.6 |
Solubility : | 29.3 mg/ml ; 0.252 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.12 |
Solubility : | 152.0 mg/ml ; 1.31 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.27 |
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 |
---|---|---|
80% | With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 3h; | To a solution of (1 r,4r)-cyclohexane-1 ,4-diol (3 g, 25.8 mmol) and (0875) imidazole(2.64 g, 38.7 mmol) in DMF (30 mL) was added TBS-CI (4.28 g, 28.4 mmol) The mixture was stirred at rt for 3 day. The mixture was diluted with water (150 mL), extracted with DCM three times. The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuum (high vacuum at 70C to remove most DMF ) to afford a light oil. The residue was loaded purified by CombiFlash, eluted with methanol in DCM (0-5%, 30 min). Collected the desired fraction and concentrated in vacuum to afford the title compound (6 g, 80%) as colorless syrup. 1 H NMR (400 MHz, DMSO-d6) delta 3.72 - 3.35 (m, 2H), 1 .80 - 1 .58 (m, 4H), 1 .37 - 1 .06 (m, 4H), 0.82 (s, 9H), 0.00 (s, 6H). |
65% | With 1H-imidazole; In N,N-dimethyl-formamide; at 0℃; for 1h; | EXAMPLE 94a Preparation of intermediate trans-4-(tert-buyl-dimethyl-silanyloxy)-cyclohexanol To a solution of <strong>[6995-79-5]trans-1,4-cyclohexanediol</strong> (3 g, 26 mmol) in anhydrous N,N-dimethylformamide (30 mL) at 0 C. was added imidazole (1.7 g, 26 mmol) and tert-butyldimethylchlorosilane (3.87 g, 26 mmol). The reaction mixture was then stirred at 0 C. for 1 h. The mixture was partitioned between ethyl acetate and water. Organic layer was separated, aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1;2) to give trans-4-(tert-buyl-dimethyl-silanyloxy)-cyclohexanol as a white solid (3.9 g, 65%). The starting material <strong>[6995-79-5]trans-1,4-cyclohexanediol</strong> was prepared by crystallization from 1:1 mixture of cis-/<strong>[6995-79-5]trans-1,4-cyclohexanediol</strong> according to procedures described by Doyle, M. P. et al in Org. Lett. 2005, Vol 7, No. 22, 5035-5038 supplimental materials without modification. |
41% | With 1H-imidazole; In dichloromethane; at 20℃; for 24h; | To a solution of (l,4-/rax)-cyclohexane-l,4-diol (70 g, 602.6 mmol) and imidazole (130 g, 1.910 mol) in dichloromethane (1.5 L) was added /er/-butyl-chloro-dimethyl- silane (100 g, 663.5 mmol) in one portion. The resultant reaction mixture was allowed to warm to room temperature and stir for 24 h, at which time TLC-analysis revealed mixture of starting material, desired product, and bis-addition product. The reaction mixture was poured into water (300 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (100 mL). The combined organic extracts were washed with water (100 mL) and brine (100 mL), dried (0779) (Na2S04), filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (800 g silica gel column, linear gradient of 0- 50percent ethyl acetate in heptane) to afford ( 1 ,4-/ra//.s)-4-[tert- butyl(dimethyl)silyl]oxycyclohexanol (58 g, 41percent) as a white solid. 1H NMR (400 MHz, DMSO-i) d 4.44 (d, J = 4.1 Hz, 1H), 3.69 - 3.50 (m, 1H), 3.48 - 3.35 (m, 1H), 1.84 - 1.60 (m, 4H), 1.37 - 1.09 (m, 4H), 0.84 (s, 9H), 0.02 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium hydride; In dimethyl sulfoxide; mineral oil; at 20℃; for 1h; | Trans-cyclohexane-l,4-diol (4.30 mmol) and sodium hydride (60percent suspension in oil, 2.15 mmol) are suspended in dry dimethylsulfoxide (4 mL) and a solution of 4-fluoro-2-trifluoromethyl-benzonitrile (2.15 mmol) in dry dimethylsulfoxide (4 mL) is added dropwise. The resulting mixture is stirred at room temperature. After 1 hour reaction time, the reaction is treated with water (10 mL), the precipitate formed is separated by filtration and the filtrate is extracted with dichloromethane (25 mL). The organic phase is washed with aqueous saturated ammonium chloride (5 mL), dried over magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The precipitate is triturated with diethylether (15 mL), filtered and the filtrate concentrated under reduced pressure. Both fractions of crude product are combined, dissolved in dichloromethane and purified by chromatography through a short pad of silica gel (dichloromethane and then diethylether as eluents) to afford the desired product (60percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With sodium hydride; In dimethyl sulfoxide; mineral oil; at 20 - 50℃; | 4-Fluoro-l-nitro-2-trifluoromethyl-benzene (11.5 mmol), trans- cyclohexane-l,4-diol (17.2 mmol), and sodium hydride (60percent in oil, 11.5 mmol) are suspended in dry dimethylsulfoxide (20 mL) and the resulting mixture is reacted under stirring for 3 hours at 500C. The reaction is allowed to reach room temperature and is then further reacted at this temperature overnight. The reaction is treated with water (20 mL), the precipitate formed is removed by filtration and the filtrate is extracted with dichloromethane (50 mL). The organic phase is washed with aqueous saturated ammonium chloride (10 mL), dried over magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The precipitate is triturated with diethylether (20 mL), filtered and the filtrate concentrated under reduced pressure. Both fractions of crude product are combined, dissolved in dichloromethane and filtered trough a short pad of silica gel to afford the desired product (36percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30.0% | To a solution of <strong>[6995-79-5]trans-1,4-cyclohexanediol</strong> (504.0 mg, 4.34 mmol) in anhydrous DMF (4 mL) was added NaH (139.0 mg, 3.47 mmol, 60percent in mineral oil) at 0° C. and then stirred at 0° C. for 1 h. The compound from step 1 (100.0 mg, 0.29 mmol) was added. The mixture was stirred at 0° C. for 0.5 h and then at r.t. 18 hrs. It was then quenched with MeOH (4 mL) and filtered. The filtrate was purified by prep-HPLC to give the title compound (37.0 mg, 30.0percent) as an off-white solid. 1H NMR (CDCl3, 40 MHz) delta 8.51 (d, J=7.6 Hz, 1H), 7.94 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H), 7.56 (t, J=6.8 Hz, 1H), 7.51 (t, J=6.8 Hz, 1H), 7.16 (d, J=7.6 Hz, 1H), 7.11 (d, J=8.8 Hz, 1H), 7.05 (s, 1H), 4.43-4.18 (m, 1H), 3.67 (s, 3H), 3.65-3.62 (m, 1H), 3.16 (q, J=7.6 Hz, 2H), 2.00-1.90 (m, 2H), 1.71-1.65 (m, 2H), 1.42-1.30 (m, 7H). LCMS (M+H)+=442.0 (M+1)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.8% | With potassium tert-butylate; In tetrahydrofuran; at 120℃; for 0.333333h;Microwave irradiation; | (lR,4R)-Cyclohexane-l,4-diol (0.105 g, 0.908 mmol) was taken into THF (5 mL) followed by the addition of potassium 2-methylpropan-2-olate in THF (0.91 mL, 0.91 mmol). The mixture was stirred for about 10 min, then (i?)-2-(2-fluoropyridin-4-yl)-8-phenyl-7,8-dihydro-6H-pyrrolo[2',r:2,3]imidazo[4,5- 6]pyridine (0.15 g, 0.454 mmol, Preparation 84) in THF (5 mL) was added and the mixture was heated at about 120 °C for about 20 min in a single mode microwave. The reaction was cooled to rt and water was added to quench the reaction. The mixture was extracted with EtOAc, dried over MgSO/i, concentrated under reduced pressure, and and purified by flash chromatography on silica gel (0-5percent MeOH/DCM) to give the title compound (0.021 g, 10.8 percent); LC/MS (Table 1, Method ab) Rt = 0.82 min; MS in ~ 427 (M+H)+. (TNF IC50 = A). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | A 5 mL microwave vial was charged with 60percent sodium hydride (70 mg, 1.750 mmol) and trans-1,4- cyclohexanediol (180 mg, 1.550 mmol), purged with nitrogen, added DMF (2 mL), and stirred the mixture for 10 min at ambient temperature. A solution of 7-(2-fluoropyridin-4-yl)-4-(2-methoxyphenyl)- 3,4-dihydro-2H-pyrano[2',3':4,5]imidazo[l,2-a]pyridine (151 mg, 0.402 mmol, Preparation 93) in DMF (2 mL) was added, and heated at 120 °C for 105 min. Quenched with water (50 mL), extracted twice with EtOAc, washed with 10 mL brine, and dried over NaaSOzi. Chromatographed on a Grace Reveleris 24g column, eluted with 0-100percent 3: 1 EtOAc:EtOH in 1 : 1 DCM:Heptane (30 mL/min), affording the title compound (83.4 mg, 44.0percent); lH NMR (400 MHz, DMSO- 6) delta 8.09 (dd, J = 5.4, 0.6 Hz, 1H), 7.93 (dd, J= 1.9, 1.0 Hz, 1H), 7.54 (dd, J= 9.3, 1.8 Hz, 1H), 7.50 (dd, J= 9.3, 1.0 Hz, 1H), 7.21 (ddd, J= 8.2, 7.4, 1.7 Hz, 1H), 7.09 - 7.02 (m, 2H), 6.90 (dd, J = 1.6, 0.8 Hz, 1H), 6.73 (td, J = 7.5, 1.1 Hz, 1H), 6.44 (dd, J = 7.6, 1.7 Hz, 1H), 4.95 - 4.85 (m, 1H), 4.82 (dd, J= 6.2, 3.5 Hz, 1H), 4.54 (d, J= 4.2 Hz, 1H), 4.25 (ddd, J = 11.2, 4.8, 3.2 Hz, 1H), 3.95 (td, J = 11.0, 2.1 Hz, 1H), 3.87 (s, 3H), 3.52 - 3.42 (m, 1H), 2.42 - 2.31 (m, 1H), 2.09 - 2.02 (m, 1H), 2.02 - 1.93 (m, 2H), 1.84 - 1.75 (m, 2H), 1.46 - 1.32 (m, 2H), 1.32 - 1.18 (m, 2H). MS (ESI+) m/z 472 (M+H). LC/MS (Table 1, ab) Rt = 0.86 min; MS m/z: 472 (M+H)+ (TNF ICso = A). |
Tags: 6995-79-5 synthesis path| 6995-79-5 SDS| 6995-79-5 COA| 6995-79-5 purity| 6995-79-5 application| 6995-79-5 NMR| 6995-79-5 COA| 6995-79-5 structure
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