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CAS No. : | 10341-26-1 | MDL No. : | MFCD02683091 |
Formula : | C5H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OXDIYMHNQAWSCL-UHFFFAOYSA-N |
M.W : | 115.13 | Pubchem ID : | 7023020 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 32.04 |
TPSA : | 38.33 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.64 cm/s |
Log Po/w (iLOGP) : | 1.17 |
Log Po/w (XLOGP3) : | -0.9 |
Log Po/w (WLOGP) : | -0.86 |
Log Po/w (MLOGP) : | -0.78 |
Log Po/w (SILICOS-IT) : | 1.02 |
Consensus Log Po/w : | -0.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.01 |
Solubility : | 119.0 mg/ml ; 1.03 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.58 |
Solubility : | 436.0 mg/ml ; 3.78 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.89 |
Solubility : | 14.7 mg/ml ; 0.128 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.6 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | 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 |
---|---|---|
85% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; ethyl acetate at 70℃; Inert atmosphere | To a solution of ketoxime (0.01 mol) in THF (10 mL) was added T3P (15 mol percent, 50percent soln in EtOAc) and the resulting reaction mixture was stirred at reflux for 1-4 h under nitrogen atmosphere. When the reaction was completed as confirmed by TLC, the solvent was removed under vacuum and the residue was diluted with water (20 mL). The product was extracted with ethyl acetate (2 .x. 20 mL) and the combined organic phase was washed with saturated NaHCO3 solution (1 .x. 10 mL) and brine. The organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford the desired amides in good purity. |
40% | Stage #1: With benzenesulfonyl chloride In acetone at 0℃; Stage #2: With sodium hydroxide In acetone at 20℃; |
Step 2Dihydro-2H-pyran-4(3H)-one oxime [105] (1 g, 8.7 mmol) was dissolved in acetone (20 ml) in a dry two neck round bottom flask. The reaction mixture was cooled to 0 °C followed by addition of benzene sulfonyl chloride[ 106] (9.6 mmol) and stirred for 15 min; after which was added dropwise 2.5 N NaOH (384 mg, 9.6 mmol). The reaction mixture was stirred at RT overnight. TLC showed complete consumption of starting material. The excess of solvent was removed under reduced pressure on rotary evaporator to yield a white solid. The product was purified by column chromatography over 100-200 silica mesh using 5percent MeOH: DCM as eluent to gave 1,4- oxazepan-5-one [107] as a light yellow solid (0.4 g, 40percent).ESIMS: 1 16.2 (M+ + 1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.4% | With hydrogenchloride; sodium azide In water at 0 - 20℃; for 17 h; | 1) 1,4-Oxazepan-5-one Under cooling on ice, sodium azide (17.8 g) was added to a solution of tetrahydro-4H-pyran-4-one (9.80 g) in concentrated hydrochloric acid (50 mL) over 40 minutes, and the mixture was stirred for 30 minutes and then at room temperature for 16 hours. Under cooling on ice, sodium carbonate was added to the reaction mixture to make the pH condition to 8 to 9, and chloroform was added thereto for partitioning the mixture. The organic layer was washed with saturated brine and then dried over magnesium sulfate anhydrate. After a filtration step, the solvent was removed under reduced pressure, to thereby give [1,4]oxazepan-5-one as a solid product (5.34 g, 47.4percent). 1H-NMR (300MHz, CDCl3) δ:2.70-2.74 (2H, m), 3.32-3.37(2H,m), 3.75-3.83(4H,m), 6.31 (1H, br s). MS(FAB)m/z:116(M+H)+. |
34.8% | at 0 - 20℃; for 8 h; | Example 83. Synthesis of 2-(4-(3-(l,4-oxazepan-4-yl)-lH-pyrazol-l-yl)-5-oxo-6,7- ihydro-5H-pyrrolo[3,4-b]pyridin-2-yl)-3-fluorobenzonitrile, 1-83 Synthesis of compound 83.2. To a cooled mixture of 83.1 (10.0 g, 99 mmol, 1.0 eq) in concentrated HC1 (52 mL) at 0 °Cwas added sodium azide (11 g, 167 mmol, 1.69 eq) portion wise. Reaction mixture was stirred at room temperature for 8 h. Upon completion of the reaction, reaction mixture was transferred into water, basified to pH=9.0 by sodium carbonate and extracted with DCM. Combined organic layers were washed with brine solution, dried over sodium sulphate and concentrated under reduced pressure to obtained crude. 83.2 . (4.0 g, 34.8percent). MS(ES): m/z 116.3 [M+H]+. |
48% | With sodium carbonate In hydrogenchloride; water | Preparation 33 1,4-Oxazepane To a stirred solution of tetrahydro4H-pyran-4-one (4.19 mL) in conc. HCl (23 mL) cooled to 0° C. is added portion-wise sodium azide (4.42 mL). After addition was complete, the reaction is stirred at room temperature for 4 h. Solid sodium carbonate is added portion-wise until the solution was slightly alkaline (pH=9). Water is added during addition of sodium carbonate to dissolve the salt. The alkaline solution is diluted with CHCl3 (125 mL) and the phases are separated. The aqueous layer are extracted with CHCl3 (2*75 mL). The combined organic layers are dried (Na2SO4), filtered, and concentrated to afford 2.5 g (48percent) of 1,4-oxazepan-5-one as an orange-brown residue. 1H NMR (300 MHz, CDCl3) δ6.66, 3.80, 3.35, 2.72. |
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