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CAS No. : | 6607-96-1 | MDL No. : | MFCD18433527 |
Formula : | C10H10N2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LWTSKMDGAXLZJJ-UHFFFAOYSA-N |
M.W : | 238.20 | Pubchem ID : | 19045257 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 61.79 |
TPSA : | 112.22 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) : | -6.79 cm/s |
Log Po/w (iLOGP) : | 0.61 |
Log Po/w (XLOGP3) : | 1.36 |
Log Po/w (WLOGP) : | 1.27 |
Log Po/w (MLOGP) : | -0.37 |
Log Po/w (SILICOS-IT) : | -0.8 |
Consensus Log Po/w : | 0.41 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.17 |
Solubility : | 1.61 mg/ml ; 0.00675 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.32 |
Solubility : | 0.114 mg/ml ; 0.00048 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.93 |
Solubility : | 2.77 mg/ml ; 0.0116 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.29 |
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 |
---|---|---|
66% | In methanol; | 7-Amino-3,4-dihydro-1'-hexyl-6-nitrospiro[(2H)-1-benzopyran-2,4'-piperidin]-4-one In the manner of Example 457, <strong>[6607-96-1]N-(4-acetyl-5-hydroxy-2-nitrophenyl)acetamide</strong> (1.07 g, 4.5 mmol), pyrrolidine (380 mul, 320 mg, 4.5 mmol) and 1-hexyl-4-piperidone (820 mg, 4.5 mmol) in methanol (15 ml) gave, after chromatography, the title compound as an orange gum (1.07 g, 66%) 1 H NMR (CDCl3): delta8.78 (1H, s), 6.4 (2H, br s), 6.28 (1H, s), 2.68 (2H, s), 2.63 (2H, m), 2.35 (4H, m), 2.00 (2H, m), 1.77 (2H, m), 1.50 (2H, m), 1.29 (6H, m), 0.88 (3H, t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | In methanol; | 7-Amino-3,4-dihydro-1'-heptyl-6-nitrospiro[(2H)-1-benzopyran-2,4'-piperidin]-4-one In the manner of Example 457, <strong>[6607-96-1]N-(4-acetyl-5-hydroxy-2-nitrophenyl)acetamide</strong> (1.07 g, 4.5 mmol), pyrrolidine (380 mul, 320 mg, 4.5 mmol) and 1-heptyl-4-piperidone (890 mg, 4.5 mmol) in methanol (15 ml) gave, after chromatography, the title compound as an orange gum (980 mg, 58%). 1 H NMR (CDCl3): delta 8.79 (1H, s), 6.4 (2H, br s), 6.28 (1H, s), 2.68 (2H, s), 2.65 (2H, s), 2.35 (4H, m), 2.01 (2H, m), 1.77 (2H, m), 1.50 (2H, m), 1.28 (8H, m), 0.88 (3H, t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; ethanol; | 7-Amino-3,4-dihydro-6-nitro-1'-[(2,3-dihydro-1H-indene)-2-yl]-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one dihydrochloride In the manner of Example 457, <strong>[6607-96-1]N-(4-acetyl-5-hydroxy-2-nitrophenyl)acetamide</strong> (1.07 g, 4.5 mmol) and 1-[(2,3-dihydro-1H-indene)-2-yl]-4-piperidinone (970 mg, 4.5 mmol) in methanol (15 ml) gave, after hydrolysis in refluxing ethanol (3 ml) and HCl-H2 O (6M, 1 ml), the dihydrochloride as a yellow solid, (0.87 g, 41%). 1 H-NMR (DMSO) delta:11.5-11.1 (1H, s), 8.47 (1H, s), 8.00 (2H, br s), 7.24 (4H, m), 6.53 (1H, s), 4.15 (1H, m), 3.47 (2H, m), 3.32 (6H, m), 2.84 (2H, s), and 2.28-2.04 (4H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; | (+-)-7-Amino-3,4-dihydro-6-nitro-1'-[(1,2,3,4-tetrahydronapthalene)-2-yl]-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one In the manner of Example 457, <strong>[6607-96-1]N-(4-acetyl-5-hydroxy-2-nitrophenyl)acetamide</strong> (1.07 g, 4.5 mmol) and (+-)-1-[(1,2,3,4-tetrahydronapthalene)-2-yl]-4-piperidinone (1.03 g, 4.5 mmol) in methanol (9 ml) gave, after acid hydrolysis in refluxing ethanol (20 ml) and HCl-H2 O (6M, 10 ml) and chromatography, the pyranone as an orange foam, (418 mg, 23%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; | 7-Amino-3,4-dihydro-6-nitro-1'-[(6,7,8,9-tetrahydro-5H-benzocycloheptene)-7-yl]-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one In the manner of Example 457, <strong>[6607-96-1]N-(4-acetyl-5-hydroxy-2-nitrophenyl)acetamide</strong> (785 mg, 3.3 mmol) and 1-[(6,7,8,9-tetrahydro-5H-benzocycloheptene)-7-yl]-4-piperidinone (802 mg, 3.3 mmol) in methanol (7 ml) gave, after acid hydrolysis in refluxing ethanol (20 ml) and HCl-H2 O (6M, 10 ml) and chromatography, the pyranone as an orange solid, (217 mg, 16%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitric acid; acetic anhydride; In dichloromethane; | N-(4-Acetyl-3-hydroxy-2-nitrophenyl)acetamide A mixture of N-(4-acetyl-3-hydroxyphenyl)acetamide (9.66 g, 50 mmol) and acetic anhydride (14.2 ml, 15.3 g, 150 mmol) in dichloromethane (150 ml) was cooled to 5 C. and nitric acid (90%, d 1.49, 4.70 ml, 7.00 g, 100 mmol) was added dropwise. The mixture was stirred at room temperature for 1 hour, poured into water (150 ml) and extracted with dichloromethane (3*150 ml). The combined organic fractions were dried (Na2 SO4) and evaporated under reduced pressure and the residue was purified by repeated flash column chromatography on silica gel, eluding with hexane/30% ethyl acetate then hexane/50% ethyl acetate. The first isomer to elute was <strong>[6607-96-1]N-(4-acetyl-5-hydroxy-2-nitrophenyl)acetamide</strong> as a yellow solid (3.87 g, 33%). 1 H NMR (CDCl3): delta12.83 (1H, s), 10.78 (1H, br s), 8.78 (1H, s), 8.43 (1H, s), 2.68 (3H, s), 2.32 (3H, s). |
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