Structure of 114686-85-0
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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. : | 114686-85-0 |
Formula : | C8H8Cl2O |
M.W : | 191.06 |
SMILES Code : | ClC1=C(Cl)C(CCO)=CC=C1 |
MDL No. : | MFCD04112742 |
InChI Key : | FJJDHDLMGJKZKV-UHFFFAOYSA-N |
Pubchem ID : | 2734759 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 47.4 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.04 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.17 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.53 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.27 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.81 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.29 |
Solubility | 0.0972 mg/ml ; 0.000509 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.27 |
Solubility | 0.104 mg/ml ; 0.000543 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.87 |
Solubility | 0.026 mg/ml ; 0.000136 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) |
Yes |
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 |
-5.21 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) |
1.42 |
* 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 |
---|---|---|
100% | a. 2-(2,3-Dichlorophenyl)ethyl methansulfonate Using the method of Example 1a, but substituting <strong>[114686-85-0]2,3-dichlorphenethyl alcohol</strong> for 3-methoxyphenethyl alcohol and reacting at 0 C. for 4 hr, the title product was obtained as a yellow oil in 100% yield. | |
100% | a. 2-(2,3-Dichlorophenyl)ethyl methansulfonate Using the method of Example 1a, but substituting <strong>[114686-85-0]2,3-dichlorphenethyl alcohol</strong> for 3-methoxyphenethyl alcohol and reacting at 0C for 4 hr, the title product was obtained as a yellow oil in 100% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; water; for 1h; | A mixture of <strong>[114686-85-0]2-(2,3-dichlorophenyl)ethanol</strong> (0.50 g), NaHCO3 (0.438 g) and Dess-Martin periodinane (1.22 g) in dichloromethane (10 mL) and water (46 mL) was stirred for 1 hour. The mixture was quenched with aqueous NaHCO3 and saturated aqueous Na2S2O3 and extracted with dichloromethane. The extract was dried (Na2SO4), filtered and concentrated. The concentrate was purified on silica gel with an Intelliflash-280 purification system with hexanes/ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | General procedure: The starting material, 2-(3,4-dimethoxyphenyl)-ethan-1-ol (521 mg, 2.86 mmol, 1.0 equiv) was dissolved in dichloromethane (20 mL) and imidazole (583 mg, 8.58 mmol, 3.0 equiv) was added. The mixture was stirred for 5 minutes. tert-Butyldimethylsilyl chloride (518 mg, 3.43 mmol, 1.2 equiv) was added and the reaction mixture was stirred at room temperature for 1 hr. Water (20 mL) and dichloromethane (20 mL) were added and the mixture was shaken in a separating funnel. The aqueous layer was separated and washed with dichloromethane (2 x 5 mL). The combined organic layers were washed with water (20 mL), brine (20 mL) and dried over MgSO4. Following filtration, the solvent was removed under reduced pressure. The crude material was purified by column chromatography on silica gel (eluting with a gradient from petroleum ether to 1:1 petroleum ether : ether) to afford 820mg of 1a (97%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With toluene-4-sulfonic acid; In methanol; dichloromethane; at 20 - 25℃; for 0.333333h;Flow reactor; | General procedure: The system (Figure 4) was primed with solvent (DCM and 0.3 M aqueous NaOH) prior to the introduction of the substrates. Substrates were present as 0.034 M solutions (20 mL) in glass vials. These were placed in a square 4 x 4 rack. Following initiation of the computer-vision system (and checking to make sure the aqueous-out tap was opening/closing properly), activation of the autosampler/liquid-handling schedule was initiated by pressing ?s? on the computer keyboard. The outlet of the flow stream for each product was then collected until the autosampler moved to the waste position between each run. 5 mL of substrate was taken up during each run, 4 mL of which entered the holding loop (the line between the autosampler and 3-way-valve 1 was 1 mL in volume). Outlet collection flasks were changed manually. The products were isolated by removing solvent under reduced pressure. |
A347966 [1875-87-2]
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