Structure of 2628-16-2
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 2628-16-2 |
Formula : | C10H10O2 |
M.W : | 162.19 |
SMILES Code : | C=CC1=CC=C(OC(C)=O)C=C1 |
MDL No. : | MFCD00075734 |
InChI Key : | JAMNSIXSLVPNLC-UHFFFAOYSA-N |
Pubchem ID : | 75821 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.1 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 48.03 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 ?2 |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.26 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.52 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.15 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.47 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.5 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.38 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.61 |
Solubility | 0.403 mg/ml ; 0.00248 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.72 |
Solubility | 0.31 mg/ml ; 0.00191 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.91 |
Solubility | 0.2 mg/ml ; 0.00123 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 |
-5.5 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 |
1.0 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 |
---|---|---|
With acetic anhydride; In palladium-carbon; | EXAMPLE 1 This example illustrates the preparation of 4-acetoxystyrene oxide from 4-acetoxystyrene under the invention, the latter compound having been prepared from 4-hydroxyacetophenone (4-HAP) as an intermediate. A solution of 136.2g (1.0 mol) of 4-hydroxyacetophenone and 400 ml of acetic anhydride was heated at reflux for 3 h under a nitrogen atmosphere. The acetic acid and acetic anhydride was distilled overhead in vacuo (30-41C, 2.6 mm Hg). The remaining oil was then distilled in vacuo (132-134C, 2.0 mm Hg) to yield 169.7g (95.2%) of white crystals identified as 4 -acetoxyacetophenone. 4-Acetoxyacetophenone (100.0 g, 0.56 mol) was hydrogenated in a Fluidtron Reactor with 5% Pd/C (3.94 g) at 100 psig. The hydrogenation was carried out at 60C for 5.25 hours. The reactor was depressurized and the catalyst removed via filtration to afford 1-(4--acetoxyphenyl)ethanol as an oil (93.6 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethylmorpholine;; thionyl chloride;palladium diacetate; In ethyl acetate; N,N-dimethyl-formamide; toluene; | (E)-3,4',5-Triacetoxystilbene 3,5-Diacetoxybenzoic acid (8.022 g, 33.706 mmol) suspended in a mixture of toluene (130 mL), DMF (500 μL) and thionyl chloride (16.00 mL, 220.6 mmol) was heated at 100 C. for three hours under an argon gas atmosphere. The solvents were removed by vacuum distillation and the residue re-suspended in toluene (85 mL) and sonicated under vacuum to remove dissolved gases. 4-Acetoxystyrene (5.74 mL, 37.5 mmol), N-ethylmorpholine (4.31 mL, 33.9 mmol) and palladium diacetate (35 mg, 0.16 mmol, 0.46 mole %) were added and the reaction heated to reflux for 2 hours. Further palladium diacetate (116 mg, 0.52 mmol, 1.54 mole %) was added and the reaction left to reflux overnight. On return to room temperature, ethyl acetate (500 mL) was added, the solution was washed with 0.1 M HCl (2*300 mL) and water (300 mL) and then dried and evaporated to return a brown solid. Purification with column chromatography (isocratically eluted with 2:1 Et2O/hexane) gave 7.888 g of a white solid, shown by 1H NMR to be predominantly the desired adduct. Further chromatography (gradient eluted starting with 4:1 hexane/EtOAc and finishing with 2:1 hexane/EtOAc) returned pure (E)-3,4',5-triacetoxystilbene (6.071 g, 51%) as a white solid. Rf 0.29 (2:1 hexane/EtOAc); mp 112.5-113.0 C. (lit mp 116 C.); (δC (CDCl3) 2.27 (s, 9H, 3*OAc), 6.80 (pseudo t, 1H, J 2.1, 4'-H), 6.93 (d, 1H, J 16.3, Htrans), 7.03 (d, 1H, J 16.3, Htrans), 7.04-7.09 (m, 4H, 3-H, 5-H, 2'-H, 6'-H) and 7.44-7.47 (m, 2H, 2-H, 6-H); δC(CDCl3) 20.07, 113.39, 115.88, 120.88, 126.19, 126.64, 128.64, 133.45, 138.53, 149.46, 150.34, 167.91 and 168.30; m/z (ESI) 377 (MNa+, 100%), 378 (21). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrabutylammomium bromide; potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 80℃; for 5h;Inert atmosphere; Sealed tube; | General procedure: To a solution of tetrabutylammonium bromide (1.100 g, 3.33 mmol), potassium acetate (0.586 g, 3.57 mmol), and palladium acetate (0.025 g, 0.11 mmol) in DMF (20 mL) were added substituted iodobenzene (2.21 mmol) and 4-acetyloxystyrene (2.44 mmol). The reaction mixture was recharged with Argon and stirred at 80C for 5 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:3) to afford the intermediate substituted (E)-4-styrylphenyl acetate. To a solution of triethylamine (2.0 mL) in MeOH (5 mL) was added substituted (E)-4-styrylphenyl acetate (1.36 mmol). The reaction mixture was stirred at reflux temperaturefor 3 h. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane/methanol, 10:0.3) to afford pure product. |