Structure of 98955-27-2
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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. : | 98955-27-2 |
Formula : | C9H18O2 |
M.W : | 158.24 |
SMILES Code : | OCC1CCC(COC)CC1 |
MDL No. : | MFCD22571682 |
InChI Key : | KSIFEWSPJQDERU-UHFFFAOYSA-N |
Pubchem ID : | 19938783 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H227-H315-H319-H335 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 45.51 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.37 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.11 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.43 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.22 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.69 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.56 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.32 |
Solubility | 7.53 mg/ml ; 0.0476 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.32 |
Solubility | 7.54 mg/ml ; 0.0477 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.44 |
Solubility | 5.81 mg/ml ; 0.0367 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 |
-6.48 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 |
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) |
2.47 |
* 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 |
---|---|---|
With NaH; In N,N-dimethyl-formamide; | 1,4-bis(Hydroxymethyl)cyclohexane (5 g, 0.0347 mol), cis/trans mixture 1:3, in anhydrous DMF (20 cm3) was added dropwise to NaH (1.6 g, 0.0366 mol, 55%) washed with hexane, under atmosphere of nitrogen. The mixture was stirred at room temperature for 1/2 h, then CH3 I (5 g, 0.0352 mol) dissolved in DMF (20 cm3) was added dropwise. After the addition was complete the solution was stirred at room temperature for 2 h; NH4 Cl solution was added then thoroughly extracted with ether, to which Na2 SO4 was added and dried under reduced pressure. Chromatography on silica gel eluding with hexane/ethyl acetate (55/45) gave 4-methoxymethyl-cyclohexylmethanol (1.8 g, 0.0113 mol) out of 4.1 g of residue. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus tribromide; | Such compound was dissolved in ether (10 cm3), cooled to -70 C. and was added dropwise with PBr3 (1.2 g, 0.0044 mol). After the addition was complete the solution was stirred to room temperature for 2 h, was extracted with ether and cautiously added with satured NaHCO3 solution. After the two layers were separated, the organic phase was added with Na2 SO4 and dried under reduced pressure. Chromatography on silica gel eluding with hexane gave 4-methoxymethyl cyclohexylmethyl bromide, cis trans mixture 1 3. Such product was employed in the example 8. 1 H-NMR (60 MHz, CCl4): delta0.6-2.2 (m), 10H; delta2.9-3.5 (m), 4H; delta3.25 (s), 3 H. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With CH3I; NaH; ammonium chloride; In N,N-dimethyl-formamide; | Under a nitrogen atmosphere, 1,4-bis(hydroxymethyl)cyclohexane (5 g, 0.0347 mol, 1:3 cis/trans mixture) in anhydrous DMF (20 ml) was added dropwise to NaH (1.6 g, 0.0366 mol, 55%) washed with hexane. The mixture was stirred at room temperature for 1/2 h, then CH3I (5 g, 0.0352 mol) dissolved in DMF (20 ml) was added dropwise. After the addition was complete the solution was stirred at room temperature for another 2 h; then NH4Cl solution was added, followed by a thorough extraction with ether. The ether extract was then dried over Na2SO4 under reduced pressure. Chromatography on silica gel, eluding with hexane/ethyl acetate (55/45), gave (4-methoxymethyl-cyclohexyl)methanol (1.8 g, 0.0113 mol) out of 4.1 g of residue. |
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