Structure of 4-(1-Phenylethyl)resorcinol
CAS No.: 85-27-8
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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. : | 85-27-8 |
Formula : | C14H14O2 |
M.W : | 214.26 |
SMILES Code : | OC1=CC=C(C(C2=CC=CC=C2)C)C(O)=C1 |
MDL No. : | MFCD21648466 |
InChI Key : | PQSXNIMHIHYFEE-UHFFFAOYSA-N |
Pubchem ID : | 11171903 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 64.75 |
TPSA ? Topological Polar Surface Area: Calculated from |
40.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.11 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.46 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.25 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.95 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.08 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.97 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.77 |
Solubility | 0.0363 mg/ml ; 0.000169 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.99 |
Solubility | 0.0219 mg/ml ; 0.000102 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.21 |
Solubility | 0.0133 mg/ml ; 0.0000621 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
-5.15 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 |
0.0 |
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) |
2.16 |
* 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 |
---|---|---|
88% | In toluene; at 95℃;Sealed tube; Inert atmosphere; Large scale; | (1) Add 50 L of toluene to the reaction vessel, start stirring, and add 39.6 kg (360 mol) of resorcinol (mw: 110.11).0.45 kg of catalyst solid acid H2SO4-SiO2 (by mass ratio H2SO4: SiO2 = 1:1),After sealing, the vacuum was evacuated and replaced with nitrogen three times. Under a nitrogen atmosphere, the reactor was heated to 95 C.After the temperature was stable, 15 kg (144 mol) of styrene (mw: 104.15) was slowly dropped.Control the feeding time 1.5-2 hours, keep the reaction for 3 hours,The reaction was completely detected by liquid phase, and the yield was 89%, and the reaction was stopped. (2) adding 10 liters of toluene to the reaction solution,Recovery of solid acid H2SO4-SiO2 catalyst by hot filtration,The filtrate was slowly cooled to 0 C under stirring, and solid resorcinol was precipitated, filtered, and solid resorcinol was washed with 12 liters (6 liters of X 2 times) of toluene for recovery.The filtrate was concentrated until a solid precipitated, and 10 liters of a mixed solvent (by volume ratio, n-hexane: toluene = 1:1) was heated to 75 C to dissolve sufficiently.After cooling to -5 C under stirring, crystals were precipitated, and the mixture was kept for 2 hours until the crystals were completely precipitated, followed by pressure filtration, and the obtained solid was washed twice with 20 liters of a mixed solvent (by volume ratio, n-hexane: toluene = 1:1).The resulting solid was dried under vacuum at 50 C.It has a white crystal of 24.2 kg and a liquid phase detection content of 98.4%.The product yield is 88%, and the product has a melting point of 76-78 C. |
83% | With H2SO4-SiO2; In toluene; at 95℃; for 2.0h;Inert atmosphere; | The preparation method is as follows: 1) under the protection of nitrogen, the 231g (2.1mol) resorcinol, 4.62g solid acid H 2 SO 4-SiO 2 and 220 ml toluene added into the reactor, heating to 95 C, keeping temperature 95 C, adding dropwisely to the reactor 104g (1mol) styrene, styrene of the control of acceleration, applied to the drop 1 drops-hour period, then the 95 C continue to reaction 1 hour, to obtain a reaction liquid. 2) filtering the reaction liquid, and removing the solid acid H 2 SO 4-SiO 2, by adding the filtrate extraction aqueous solution of sodium bicarbonate 150ml0.5%, takes organically phase, then using deionized extraction secondary (2 × 150 ml), takes organically , the toluene turns on lathe does , by adding 250 ml hexane and toluene mixed solution (1:5v/v), recrystallization, separating white crystalline 177.6g, the yield is 83%. |
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