Structure of 4-Fluorobenzyl alcohol
CAS No.: 459-56-3
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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. : | 459-56-3 |
Formula : | C7H7FO |
M.W : | 126.13 |
SMILES Code : | OCC1=CC=C(F)C=C1 |
MDL No. : | MFCD00004651 |
InChI Key : | GEZMEIHVFSWOCA-UHFFFAOYSA-N |
Pubchem ID : | 68022 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 32.53 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.76 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.36 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.59 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.97 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.12 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.76 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.91 |
Solubility | 1.57 mg/ml ; 0.0124 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.39 |
Solubility | 5.17 mg/ml ; 0.041 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.46 |
Solubility | 0.433 mg/ml ; 0.00344 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 |
-6.1 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) |
1.0 |
* 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 |
---|---|---|
72%Chromat. | General procedure: Various N,N-dimethyl benzamides were obtained followinga simple procedure which involves charging the reactionmixture containing benzyl alcohols (1mmol), catalyst(20wt%) and DMF (5mL) into a two necked 50mL roundbottom flask (RBF) and stirred for 10min at RT and then70% aqueous TBHP (5mmol) was introduced dropwiseto the mixture under continuous stirring at RT. The RBFwas fitted with a water condenser and heated for 24h at100C. After 24h, the reaction mixture was cooled to RTand catalyst was then separated by filtration. The reactionmixture was diluted with 100mL of DW and extractedusing ethyl acetate (2 × 60mL). The combined organiclayer was dried using Na2SO4and concentrated underrotatory evaporator. The crude products were purified bychromatography using silica gel, hexane and ethyl acetate.Similarly a range of N,N-substituted benzamides werealso obtained by taking the stoichiometric amount of variousN-substituted formamides in 5mL of toluene keepingother parameters constant. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 80℃; for 3h; | General procedure: 2-Chloro-4-(trifluoromethyl)-benzonitrile(1.00 mmol) was dissolved in appropriate alcohol, and DBU(2.00 mmol) was added. The mixture was stirred for 3 h at 80 C.The reaction was quenched with water and extracted with EtOActwice. The combined organic extracts were dried over MgSO4,filtered, and concentrated in vacuo. The residue was purified byflash column chromatography on silica gel using EtOAc/hexane(1:4) eluant condition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 4-Fluorobenzyl bromide; at 130℃; for 12h;Green chemistry; | <strong>[4214-79-3]2-hydroxy-5-chloropyridine</strong> (0.259 g, 2 mmol), 4-fluorobenzyl alcohol (2.4 mmol,1.2 equiv.) And 4-fluorobenzyl bromide (0.0498 ml, 20 molpercent)were added successively to a tubular reactorSealed in air, and thenheated to 130 ° C for 12 hunder solvent-free conditions.After the TLC monitoring reaction was complete, the product was purified by column chromatography and the yield was 93percent |
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