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CAS No. : | 18684-63-4 | MDL No. : | MFCD00218769 |
Formula : | C8H14O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BDNQWBJLWGNPAL-UHFFFAOYSA-N |
M.W : | 126.20 | Pubchem ID : | 140410 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 37.5 |
TPSA : | 20.23 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) : | -5.66 cm/s |
Log Po/w (iLOGP) : | 1.96 |
Log Po/w (XLOGP3) : | 1.99 |
Log Po/w (WLOGP) : | 1.56 |
Log Po/w (MLOGP) : | 1.83 |
Log Po/w (SILICOS-IT) : | 1.68 |
Consensus Log Po/w : | 1.8 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.88 |
Solubility : | 1.68 mg/ml ; 0.0133 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.04 |
Solubility : | 1.15 mg/ml ; 0.0091 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -0.79 |
Solubility : | 20.5 mg/ml ; 0.163 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.09 |
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 |
---|---|---|
87% | With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In 1,1-dichloroethane; for 1.0h;Reflux; | Preparation of bicyclo[2.2.2]octan-2-one (7) A mixture of bicyclo[2.2.2]octan-2-ol 6 (0.710 g, 5.72 mmol) and 1-hydroxy-1,2-benziodoxol-3H-one-1-oxide (2.40 g, 8.59 mmol) in dichloroethane (20 mL) was refluxed for 1 h, filtered through a pad of celite, washed with dichloromethane and concentrated to provide 7 (0.62 g, 87%) as a white solid. 1H NMR (400 MHz, CDCl3): delta 1.62 (2H, m), 1.70 (2H, m), 1.82 (4H, m), 2.15 (1H, m), 2.25 (3H, m) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | [2.2.2]oct-2-ene. Hydroboration of the bicyclic octene with borane-methyl sulfide (BMS) gave the bicyclic alcohol 11 in 70% yield. | |
70% | Bicyclo[2.2.2]octan-2-ol (11). Hydroboration of commercially available bicyclo[2.2.2]oct-2-ene was accomplished by reacting 1 equivalent of the octene with 0.37 equivalent of borane-methyl sulfide complex and 1.1 equivalent of hydrogen peroxide in anhydrous ethyl ether. The pure alcohol, as white crystals, was recovered in 70% yield after vacuum sublimation. mp 215 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.32 g (32%) | With triphenylphosphine; In tetrahydrofuran; | 3-(bicyclo-[2.2.2]oct-2-yloxy)-4-Methoxybenzaldehyde Bicyclo[2.2.2]-2-octanol (5.00 g, 40 mmol), isovanillin (6.09 g, 40 mmol) and triphenylphosphine (13.1 g, 50 mmol) are dissolved in dry tetrahydrofuran. To this reaction mixture is added dropwise diethylazodicarboxylate (8.71 g, 50 mmol). The reaction is stirred for 1 hour at room temperature and is refluxed for 80 hours. The reaction mixture was cooled and concentrated in vacuo and the residue is mashed 3*150 ml of ether to remove the desired material from the triphenylphosphine oxide. The combined ethereal layers are washed with 2*100 ml H2 O, 2*100 ml 2N NaOH solution, 2*100 ml H2 O and 2*100 ml brine. The organics are dried, filtered and concentrated in vacuo. The compound is purified by flash silica gel (32-80 mesh) chromatography with 20% ethyl acetate/hexane. The appropriate fractions are concentrated in vacuo to yield 3.32 g (32%) of product as a viscous oil. 1 H NMR (250 MHz, CDCl3): delta 7.4 (dd, 1H, J=8.5 Hz, J=1.5 Hz), 7.35 (d, 1H, J=1.5 Hz), 6.95 (d, 1H, J=8.5 Hz), 4.52 (m, 1H), 3.91 (s, 3H), 2.2-1.3 (m, 12H). 13 C NMR (63 MHz, CDCl3): delta 190.9, 155.7, 147.9, 129.97, 126.2, 112.6, 110.9, 77.5, 56.1, 34.74, 28.18, 25.25, 24.55, 23.29, 22.78, 19.09 (16 lines). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19.27 g (83%) | With sodium hydroxide; In tetrahydrofuran; | PREPARATION F Bicyclo[2.2.2]octan-2-ol Bicyclo[2.2.2]-2-octene (20 g, 185 mmol) is dissolved in 100 ml of dry tetrahydrofuran and cooled to 0 C. To this is added borane-tetrahydrofuran complex (200 mmol) dropwise as a 1M solution in tetrahydrofuran. The reaction is warmed slowly to room temperature where it is stirred for 1 hour. The reaction is quenched slowly with 50 ml of 2N NaOH solution and 10 ml of 30% H2 O2 and is warmed to 50 C. for 1 hour. The solution is diluted with 500 ml ethyl ether. The aqueous layer is saturated with NaCl and extracted with 100 ml ether. The organics are washed with 1*100 ml saturated sodium bisulfite solution, 1*100 ml water and 1*100 brine. The ethereal layer is dried with anhydrous Na2 SO4, filtered and concentrated in vacuo to yield 19.27 g (83%) of the bicyclooctanol as a white solid. MP: 210-212 C. 1 H NMR (90 MH2, CDCl3): delta 3.93 (m, 1H), 2.5 (bs, 1H), 2.3-1.0 (m, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With hydrogen;5%-palladium/activated carbon; In methanol; at 20.0℃; under 1551.49 Torr; for 1.0h; | Preparation of bicyclo[2.2.2]octan-2-ol (6) A mixture of bicyclo[2.2.2]oct-5-en-2-one 5 (0.820 g, 6.56 mmol) and Pd/C (5%, 0.30 g) in MeOH (100 mL) was hydrogenated under 30 psi at room temperature for 1 h. The mixture was filtered through a pad of celite and concentrated to provide 6 (0.71 g, 86%) as a colorless oil. 1H NMR (400 MHz, CDCl3): delta 1.61 (2H, m), 1.71 (2H, m), 1.82 (4H, m), 2.15 (1H, m), 2.25 (3H, m), 3.49 (1H, d, J=4.8 Hz) |
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