Structure of 122-72-5
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CAS No. : | 122-72-5 |
Formula : | C11H14O2 |
M.W : | 178.23 |
SMILES Code : | CC(OCCCC1=CC=CC=C1)=O |
MDL No. : | MFCD00026216 |
InChI Key : | JRJGKUTZNBZHNK-UHFFFAOYSA-N |
Pubchem ID : | 31226 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.36 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 51.92 |
TPSA ? Topological Polar Surface Area: Calculated from | 26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 2.5 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 2.53 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 2.18 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 2.58 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 2.75 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 2.51 |
Log S (ESOL):? ESOL: Topological method implemented from | -2.55 |
Solubility | 0.502 mg/ml ; 0.00282 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -2.73 |
Solubility | 0.333 mg/ml ; 0.00187 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -3.69 |
Solubility | 0.0367 mg/ml ; 0.000206 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 | -5.59 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) | 1.21 |
* 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 dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | Acetyl chloride (13.66 g) was added into a solution of 3 -phenyl- 1-propanol (15.8 g), Et3N (32.3 mL) and DMAP (1.417 g) in dichloromethane (DCM) (250 mL) at 0 C dropwise. The resultant mixture was stirred at the same temperature. After 1 hour, the mixture was allowed to warm to room temperature and stirred overnight. The mixture was washed with 1 M HC1 and brine. The organic phase was then dried over anhydrous Na2SC>4. After filtration, the filtrate was concentrated in vacuo to afford 3-phenylpropyl acetate (11.8 g) as a yellow oil. -NuMuRho (400 MHz, CDC13) delta ppm 1.93-2.01 (m, 2H), 2.06 (s, 3H), 2.69 (t, J= 7.2 Hz, 2H), 4.09 (t, J= 6.4 Hz, 2H), 7.18-7.22 (m, 3H), 7.26-7.31 (m, 2H); MS(ES+) m/z 179 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
>= 99% | With C40H56N2RuSi4; hydrogen; In toluene; at 25℃; under 7600.51 Torr; for 6h;Schlenk technique; Autoclave; | A magnetic stirrer was placed in a 20 mE Schlenk tube and the tube was dried by heating under a reduced pressure of 5 Pa, after which the tube interior was purged with argon. Ruthenium Complex C (7.7 mg, 0.010 mmol) was added as the catalyst to this Schlenk tube and dissolved in toluene (2 mE). To this solution was added cinnamyl acetate (176 mg, 1 .0 mmol). The resulting solution was transferred to an autoclave and the interior of the autoclave was purged with hydrogen. Next, the solution was stirred for 6 hours at roomtemperature under a hydrogen atmosphere at a pressure of 10 atmospheres. Anisole was added as an internal reference, the ?H-NMR spectrum was measured, and the structure and yield of the product were determined. The structure of the resulting compound was confirmed from the ?H and ?3C- NMR spectra. These results are shown as Entry 10 in Table6.?H-NMR (400 MHz, CDC13) &1.96 (m, 2H,PhCH2CH2CH2-), 2.06 (s, 3H, Me), 2.70 (m, 2H, 2H,PhCH2CH2CH2-), 4.09 (t, 2H, J6.8 Hz,PhCH2CH2CH2-), 7.17-7.23 (m, 3H, Ph), 7.27-7.32 (m,2H, Ph).?3C-NMR (100 MHz, CDC13) &21.1, 30.3, 32.3, 64.0,126.2, 128.5, 128.6, 141.3, 171.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminum (III) chloride; In dichloromethane; at 0℃; for 8h;Inert atmosphere; | Acetyl chloride (2.64 g) was added into a mixture of aluminium chloride (3.74 g) and<strong>[122-72-5]3-phenylpropyl acetate</strong> (5 g) in dichloromethane (DCM) (50 mL) at 0 C dropwise under N2. Then more aluminium chloride (3.74 g) was added. The resultant mixture was stirred at 0 C for 8 hours. The reaction mixture was poured into cold 2 M HC1 slowly, and then diluted with water. The obtained mixture was extracted with DCM for 3 times. The combined organic layers were dried over anhydrous Na2SC>4. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (EtOAc : PE = 0-15 %) to afford 3-(4- acetylphenyl)propyl acetate (5.7 g) as a yellow oil. LH-NMR (400 MHz, CDC13) delta ppm 1.95-2.05 (m, 2H), 2.06 (s, 3H), 2.59 (s, 3H), 2.76 (t, J= 8.0 Hz, 2H), 4.09 (t, J= 6.4 Hz, 2H), 7.28 (d, J= 8.4 Hz, 2H), 7.90 (d, J= 8.0 Hz, 2H); MS(ES+) m/z 221 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With 2-N,N-dimethylaminopyridinium saccharinate; In neat (no solvent); at 25℃; for 6h; | General procedure: The alcohol (2mmol) and the anhydride (2.2mmol) were mixed in a 10mL test tube and 1mol% of salt A (0.02mmol) was added. The tube was then capped (or under N2 purge) and the reaction mixture was stirred at room temperature (except for 1-methylcyclopentanol at 60C). After a couple of hours the acid effluent was evaporated in vacuum. The residue was then allowed to cool to room temperature and the salt was precipitated by adding 2mL hexane (or toluene). After filtration, salt was recovered, and then evaporating solvent from the filtrate afforded the crude ester product. The recovered salt was charged with the substrates, and the reaction mixture was then proceeded to the next run. The products were quantified with GC analysis by comparison to NMP as an internal standard. The products from the 1st run were further purified by column chromatography, and the isolated yields were compared with the GC/MS yields. They were all in good agreement. |
93% | With rice husk ash/TiO2 nanocomposite; In neat (no solvent); at 20℃; for 0.233333h;Green chemistry; | General procedure: 1 mmol of the substrate (alcohol, phenol or amine) wasadded to a mixture of RHA/TiO2(30%) (20 mg) and aceticanhydride (1.5 mmol per OH/NH2 group) and the resulting mixture was stirred at room temperature. After completionof the reaction (mentioned by TLC), dichloromethane(20 mL) was added and the catalyst was separated byfiltration. The organic phase was washed with 10% aqueoussolution of sodium bicarbonate (2 20 mL) and dried overNa2SO4. The solvent was removed under reduced pressureto afford the desired product in good to high yields. Thespectral (IR, 1H and 13C NMR) data of new compounds arepresented below: |
92% | With iron(III) p-toluenesulfonate hexahydrate; In neat (no solvent); at 0℃; for 1h; | General procedure: A homogenous mixture of cinnamyl alcohol (0.998 g, 7.44 mmol) and acetic anhydride (0.987 g, 0.91 mL, 9.67 mmol) was stirred as Fe(OTs)3·6H2O (0.101 g, 0.1487 mmol, 2.0 mol %) was added. The progress of the reaction was followed by GC. After 15 min, aqueous 10% Na2CO3 (10 mL) was added and the mixture was stirred for 10 min. The reaction mixture was extracted with ethyl acetate (2 × 20 mL). The combined organic layers were washed with saturated aqueous NaCl (15 mL), dried (Na2SO4), and concentrated on a rotary evaporator to yield 1.248 g (95%) of a clear, slightly yellow liquid that was identified as cinnamyl acetate and was determined to be >98% pure by 1H & 13C NMR spectroscopy, and 96% pure by GC. |
89% | With 20CuO-ZnO nanocatalyst; In dichloromethane; at 20℃; for 0.333333h;Green chemistry; | General procedure: A heterogenous mixture of alcohol (1 mmol), acetic anhydride (1.2 mmol) and the 20CuO-ZnO nanocatalyst (0.05g) in CH2Cl2 (10 mL) was stirred at room temperature. Upon completion of the reaction, as determined by TLC, the mixture was filtered to recover the catalyst. The catalyst was washedwith CH2Cl2 (5 mL) and then dried at X C for Y h before beingused in consecutive runs. The combined organic layers were washed sequentially with 5% (w/v) NaHCO3 solution and water and then dried over MgSO4. The solvent was then removed in vacuo to give the crude product as a residue, which was purified by column chromatography over silica gel to afford the pure desired products in high yield. |
86% | In neat (no solvent); at 75℃; for 0.5h; | General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC-MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10% solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC-MS, FT-IR, and 1H-NMR spectral data by comparing thesespectra with those of standard samples or literature data. |
69% | With triethylammonium acetate; at 20℃; for 3h; | General procedure: To a stirred solution of 2-naphthol (0.2 mmol) in TEAA(2 ml), was added acetic anhydride (0.22 mmol). The solutionwas stirred for 3 hours at room temperature. After consumptionof starting material (TLC monitoring, ethyl acetate/hexane, 2:8), the product formed was diluted with 1 mlH2O and extracted with 3 x 2 ml ether. The combined organiclayer was separated, dried (Na2SO4), and evaporatedunder reduced pressure to afford the desired product. 1H and13C NMR spectra were in full accordance with the structureproposed. The water in the aqueous layer was distilled under reduced pressure leaving behind the TEAA which was furtherrecycled. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With zinc(II) oxide; for 3h;Reflux; | General procedure: To a mixture of acetic acid (5 mL) and alcohol (1 mmol), ZnO nanopowder (0.05 mmol) was added. The mixture was stirred vigorously under reflux conditions for 3 hr. The reaction was monitored by TLC (CCl4: EtOAc, 4:1). Then, the reaction mixture was washed with an aqueous solution of sodium bicarbonate (20%) and filtered. The filtrate was extracted with ether (3 × 50 mL), washed with H2O (3× 10 mL) and dried over anhydrous magnesium sulfate. Evaporation of solvent under reduced pressure gave the desired acetate in specified yield (Table I). All the acetates were known and characterized according to their IR, 13C and 1H NMR spectra. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | General procedure: The alcohol (0.5 mmol) and KOtBu (1.0 mmol) were taken in a two-neck round bottomed flask and then purged with nitrogen gas. Then 2 mL of dimethylsulphoxide (DMSO) was added to it and the reaction mixture was stirred at room temperature for 10 min. Then 1.0 mL of EtOAc was added to it and the stirring was contunued for an additional 10 minutes. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate (3 x 20 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, evaporated under reduced pressure. Then the crude product was purified by column chromatography using silica gel (60-120 mesh) and hexane/EtOAc as eluent. | |
With Novozyme-435; at 20℃; for 24h;Sealed tube; Enzymatic reaction; | General procedure: The experiments were performed with 100 mg of substrate, 5 mg of Novozyme-435 and 5 mL of ethyl acetate (Tables 2 and 3). The suspension containing a mixture of the lipase and the corresponding substrate in ethyl acetate was stirred with a magnetic stirring bar in a test tube sealed with a cap at room temperature, being monitored by TLC. After reaction completion, the stirring was stopped and the solution filtered through a cotton plug. The solvents were evaporated under vacuum and the residue analyzed by 1H and 13C NMR spectra (provided in the supplemental information) to confirm the structure and determine the percentage of conversion of the primary alcohols into their corresponding acetylated forms |
Tags: 122-72-5 synthesis path| 122-72-5 SDS| 122-72-5 COA| 122-72-5 purity| 122-72-5 application| 122-72-5 NMR| 122-72-5 COA| 122-72-5 structure
A533701 [151-05-3]
2-Methyl-1-phenylpropan-2-yl acetate
Similarity: 0.84
A533701 [151-05-3]
2-Methyl-1-phenylpropan-2-yl acetate
Similarity: 0.84
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Total Compounds: mg
The concentration of the dissolution solution you need to prepare is mg/mL