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CAS No. : | 18437-67-7 | MDL No. : | MFCD07127701 |
Formula : | C12H17NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VZMVGGAQYQVROP-UHFFFAOYSA-N |
M.W : | 207.27 | Pubchem ID : | 4935444 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.42 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 61.65 |
TPSA : | 38.33 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.24 cm/s |
Log Po/w (iLOGP) : | 2.82 |
Log Po/w (XLOGP3) : | 3.27 |
Log Po/w (WLOGP) : | 3.15 |
Log Po/w (MLOGP) : | 2.65 |
Log Po/w (SILICOS-IT) : | 2.16 |
Consensus Log Po/w : | 2.81 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.22 |
Solubility : | 0.126 mg/ml ; 0.000607 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.75 |
Solubility : | 0.0369 mg/ml ; 0.000178 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.74 |
Solubility : | 0.0375 mg/ml ; 0.000181 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.98 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P270-P301+P312-P330 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
97% | In neat (no solvent); at 100℃; for 0.0833333h;Microwave irradiation; Green chemistry; | General procedure: Amine (1 mmol) and di-tert-butyl dicarbonate [(Boc)2O] (1.1 mmol) were placed in a microwave reaction vial. The LG microwave oven MG 555f was programmed to 300 W at 100 C. The reaction was monitored using TLC. After the reaction, ice water was added to the reaction mixture which resulted in the precipitation of the product. The solid product was merely filtered off and washed with excess cold water. The product was pure enough for all practical purposes. For characterization purpose, it was further purified by column chromatography (Neutral Alumina as adsorbent, solvent system: Hexane: Ethyl acetate (7.5:2.5)). |
91% | With nano-sphere silica sulfuric acid; In neat (no solvent); at 20℃; for 0.333333h;Large scale; | General procedure: An amine (5 mmol) was added to a magnetically stirred mixture of NS-SSA (5 mg) and di-tert-butyl dicarbonate (5.5 mmol, 1.19 g) at room temperature. After completion of the reaction (as monitored by TLC), the reaction mixture was diluted with EtOH (5 mL) and centrifuged for 3 minutes. Then, the clear liquid was separated, and the residue containing the catalyst was kept for recovery. EtOH was distillated off under vacuum to yield the highly pure N-Boc derivative. |
85% | With iron oxide; In ethanol; at 20℃; for 1.66667h;Green chemistry; | General procedure: A round-bottom flask (10 mL), which contains EtOH(5 mL), was charged with a solution of diboc (1-2 mmol),nano-Fe3O4 (3 mol%, 0.007 g) and the amine (1 mmol). The mixture was stirred at room temperature for the appropriate time (Table 3). After completion of the reaction, the catalyst was collected by a magnet and separated from the solution of product and the remaining starting materials.After drying and evaporation of the solvent, the resulting solid was recrystallized from n-hexane or ethyl acetate(5 mL) to give the pure product. The recovered catalyst was washed with EtOH, dried and reused for the next run. The catalyst was recovered and reused for six times without any significant changes in the yield and the reaction time. |
70% | For the N-boc protection of amines, to solution of diboc (1 mmol) in ethanol (5 ml) was added {K*18-crown-6]Br3}n (0.001 mmol). The solution was stirred at room temperature for 1 min. The amine (1 mmol) was then added and solution as stirred at room temperature for an appropriate time (table 1). After completion of the reaction, the solvent was removed by water bath distillation. To the residue was added ethyl acetate (5 ml) and the mixture was filtered (the catalyst is insoluble in n-hexane and ethyl acetate). The solid was washed with ethyl acetate ()10 ml*2) amd combined filtrates were reduced to dryness to yield the pure products. | |
In ethanol; at 20℃; | General procedure: Si: To a solution of anilines in ethanol was added (Boc)20 (1.1 equiv.) at room temperature. After the reaction was completed, the solution was concentrated under vacuum to afford the Boc-protected amines in high yield. The Bocprotected amines were used for next step without further purification. [Vilaivan, Tetrahedron Lett 47, 6739- 6742 (2006).] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(eta3-allyl-mu-chloropalladium(II)); sodium t-butanolate; In water; at 50℃; for 16h;Inert atmosphere; | General procedure: Amine (1.2 equiv) and 3-bromotoluene (1 equiv) were added to an aqueous solution of TPGS-750-M-2% (1 mL/mmol). The mixture was degassed by bubbling Argon in through (5 min). NaO-t-Bu (1.5 equiv), of [(allyl)PdCl]2 (1.1%) and cBridp (4.4%) were added together to the previous solution. The mixture was stirred (at 1200 rpm) at 50 C (2-24 h). Volatiles were evaporated and the crude residue was purified by chromatographic column on silica gel using ethyl acetate and cyclohexane as solvent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; In toluene; at 85℃; for 18h;Sealed tube; | General procedure: To a mixture of tert-butyloxycarbamates (8.0 mmol), K3PO4 (16 mmol), CuSO4*5H2O (0.8 mmol), and 1,10-phenanthroline (1.6 mmol) in a reaction vial was added a solution of bromoalkyne (8.8 mmol) in toluene (15 mL).The reaction mixture was capped and heatedin an oil bath at 85 C for 18 h while being monitored with TLC analysis. Upon completion, the reaction mixture was cooled to room temperature and diluted with EtOAc and filtered through Celite, and the filtrate was concentrated in vacuum. The crude products were purified by silica gel flash chromatography on a silica gel column with petroleum ether (PE) and ethylacetate (EA) as eluent to afford directing products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a solution of Boc-protected anilines Si (1.2 equiv.) in DMF was added NaH (3.0 equiv.) at 0 00, and the resulting mixture was allowed to warm up to room temperature for 30 mm. The mixture was cooled to 0 C again, then 2-chloromethyl-4-methoxy-3, 5-dimethylpyridine hydrochloride (1.0 equiv.) was added into the mixture slowly. The resulting mixture was allowed to warm up to room temperature for another 12 hours. After the reaction completed, EtOAc was added to dilute the reaction mixture, then the organic phase was washed with water, brine and dried over Na2SO4. After concentrated by rotatoryevaporation, the residue was purified by silica gelchromatography to afford the desired substrates la-w.; tert-Butyl ((4?-methoxy-3 , 5-dimethylpyridin-2-yl)methyl)(m-tolyl) carbainate (la)Colorless solid, mp = 73 C, ?H NMR (400 MHz, CDC13) 6 8,15(s, 1H), 7.10 (t, J = 7,7 Hz, 1H), 7.06 (s, 1H), 7.02 (d,J = 8.1 Hz, 1H), 6.91 (d, J = 7.5 Hz, 1H), 4.90 (s, 2H),3.72 (s, 3H), 2.27 (s, 3H), 2.21 (s, 6H), 1.39 (s, 9H); ?3CNMR (150 MHz, CDC13) 6 163.62, 155.18, 154.78, 148.91,142.70, 138.03, 128.05, 126.95, 126.29, 124.57, 123.68,123.50, 80.14, 59.83, 53.54, 28.25, 21.34, 13.19, 10.40;HRMS (ESI-TOF) m/z Calcd for C21H29N203 EM+H]: 357.2173,found: 357.2172. |
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