Structure of 770-71-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 770-71-8 |
Formula : | C11H18O |
M.W : | 166.26 |
SMILES Code : | OCC12CC3CC(C2)CC(C3)C1 |
MDL No. : | MFCD00074751 |
InChI Key : | MDVGOOIANLZFCP-UHFFFAOYSA-N |
Pubchem ID : | 64556 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 49.55 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.33 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.45 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.2 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.74 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.45 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.43 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.35 |
Solubility | 0.746 mg/ml ; 0.00448 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.52 |
Solubility | 0.504 mg/ml ; 0.00303 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.77 |
Solubility | 2.84 mg/ml ; 0.0171 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) |
No |
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 |
-5.57 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 |
2.0 |
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 |
0.0 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) |
3.79 |
* 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 |
---|---|---|
84% | With hydrogen bromide; zinc dibromide; In water; | 2. Preparation of 1-adamantyl methyl bromide To 39 g (0.17 moles) of zinc bromide, 29.8 g (0.17 mole) of hydrobromic acid were added. To the solution thus obtained, 11.5 g (0.069 mole) of 1-adamantyl methylalcohol which was prepared by the method shown in (1) was added and the mixture was refluxed for 11 hours. After the reaction mixture was brought to room temperature, 200 ml of water were added to this and extracted with two 300 ml portions of ether. After washing with 100 ml of water saturated with sodium bicarbonate and 100 ml of water, the resulting ether layer was dehydrated with anhydrous magnesium sulfate and was filtered. Ether was then distilled away. Residual solids were recrystallized from methanol or sublimed (1 mmHg, 75 C) to purify it, and 13 g of 1-adamantyl methyl bromide were obtained. Melting point of the product was 37-39 C and the yield was 84%. |
With bromine; triphenylphosphine; In N-methyl-acetamide; water; Petroleum ether; | Preparation of 1-Bromomethyladamantane, IV To 1-Hydroxymethyladamantane (366 gm.) and triphenylphosphine (598 gm.) in 1600 ml. dimethylformamide was added a solution of 366 gm. bromine in 800 ml. dimethylformamide over a 5 hour period. The mixture was left overnight at room temperature and then distilled (under aspirator) to remove solvent and product. The distillate was poured into 8 liters of water and filtered. The solid was dissolved in petroleum ether (30-60), washed with K2 CO3 solution, then with water, dried, and concentrated to dryness. The residue recrystallized from 2.5 liters methanol gave 426.6 gm., m.p. 43-4. (1st crop plus additional crops obtained on concentration of the mother liquors.) | |
With bromine; triphenylphosphine; In N-methyl-acetamide; water; Petroleum ether; | Preparation of 1-Bromomethyladamantane, IV To 1-Hydroxymethyladamantane (366 gm.) and triphenylphosphine (598 gm.) in 1600 ml. dimethylformamide was added a solution of 366 gm. bromine in 800 ml. dimethylformamide over a 5 hour period. The mixtue was left overnight at room temperature and then distilled (under aspirator) to remove solvent and product. The distillate was poured into 8 liters of water and filtered. The solid was dissolved in petroleum ether (30-60), washed with K2 CO3 solution, then with water, dried, and concentrated to dryness. The residue recrystallized from 2.5 liters methanol gave 426.6 gm., m.p. 43-4. (1st crop plus additional crops obtained on concentration of the mother liquors.) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With hydrogen bromide; In neat (no solvent);Reflux; | Adamantane-1-yl-methanol (2.9 g, 17.44 mmol, 1eq) and ZnBr2 (10.2 g, 45.34 mmol, 2.6 eq.) were suspended in 60 mL of HBr aq. in a Schlenk flask fitted with a reflux condenser and the suspension was refluxed at 125C overnight. The flask was cooled to room temperature and its contents collected with 100 mL of distilled water and extracted with EtOAc (2×100 mL). The organic layer was washed with water (2×100 mL) and brine (100 mL) and dried over anhydrous MgSO4 and evaporated to yield a brown coloured liquid which was purified by column chromatography using pure petroleum ether as the eluent (Rf=0.8) to give a yellow coloured oil. |
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