Structure of 446292-04-2
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CAS No. : | 446292-04-2 |
Formula : | C10H10N2O4 |
M.W : | 222.20 |
SMILES Code : | [O-][N+](=O)C1=CC=C(C=C1)N1CCOCC1=O |
MDL No. : | MFCD08236741 |
InChI Key : | OWMGEFWSGOTGAU-UHFFFAOYSA-N |
Pubchem ID : | 11447375 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 61.19 |
TPSA ? Topological Polar Surface Area: Calculated from |
75.36 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.62 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.77 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.58 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.66 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.59 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.61 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.85 |
Solubility | 3.15 mg/ml ; 0.0142 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.93 |
Solubility | 2.59 mg/ml ; 0.0117 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.86 |
Solubility | 3.07 mg/ml ; 0.0138 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 |
No |
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 |
-7.11 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 |
0.0 |
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 |
2.0 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) |
1.91 |
* 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 nitric acid; acetic anhydride; at 0 - 25℃; for 5h; | A mixture of 177 g (1 mol) of <strong>[29518-11-4]4-phenyl-3-morpholinone</strong>,Acetic anhydride 1200ml added to the reactor,After cooling to a temperature of 0 C, 145 g (1.5 mol) of nitric acid was added dropwise and reacted at room temperature for 5 h. After recovering part of the solvent, the mixture was stirred with 3000 ml of water, filtered, washed with water and the methyl ethyl ketone was recrystallized and dried to give 190 g of pale yellow solid, 85%. |
83% | With sulfuric acid; nitric acid; at -10℃; for 1h; | Example 2: Preparation of 4-(4-nitrophenyl)morpholin-3-one (compound XI). To a solution of <strong>[29518-11-4]4-phenylmorpholin-3-one</strong> (19.9 g, 0.1 1 mol) in 95% H2S04 (46.6 ml_,) cooled to -10 C was carefully added dropwise during 45 min 65% HNO3 (8 ml_(). The reddish solution obtained was stirred at this temperature for 1 h and H20 (110 mL) was added. The mixture was neutralized with 35% NH4OH until pH=7. The resulting precipitate was filtered, washed with cold water and dried, affording 4-(4-nitrophenyl)morpholin-3-one (or compound XI) (20 g, 83%) as a brown solid.1H NMR (200 MHz, CDCI3) delta 8.27 (d, J = 9.4 Hz, 2 H), 7.62 (d, J = 9.4 Hz, 2 H), 4.38 (s, 2 H), 4.08 (t, J = 5.0 Hz, 2 H), 3.85 (t, J = 5.0 Hz, 2 H). |
83% | With sulfuric acid; nitric acid; at -10℃; for 1h; | To a solution of<strong>[29518-11-4]4-phenylmorpholin-3-one</strong> (19.9 g, 112.3 mol) in 98% H2SO4(46.6 ml) cooled to -10 C was carefully added dropwise during 45 min 65% HNO3(8 ml). The reddish solution obtained was stirred at this temperature for 1 hand H2O (110mL) was added. The mixture was neutralizedwith 35% NH4OH until pH=7. The resulting precipitate was filtered,washed with cold water and dried, affording the desired product (20 g, 83%yield) as a brown solid. 1H NMR (300 MHz, CDCI3) delta: 8.27(d, J = 9.4 Hz, 2 H), 7.62 (d, J = 9.4 Hz, 2 H), 4.38 (s, 2 H), 4.08(t, J = 5.0 Hz, 2 H), 3.85 (t, J = 5.0 Hz, 2 H). |
81% | With sulfuric acid; nitric acid; for 2h;Cooling with ice; | 0.177 g of <strong>[29518-11-4]4-phenyl-3-morpholinone</strong> was added to the round bottom flask.Add 98% concentrated sulfuric acid 2.8mL 50mmol,Stir and dissolve, then slowly add 65% concentrated nitric acid 0.1mL 14mol in an ice bath, continue to stir the reaction for 2h,4-(4-Aminophenyl)-3-morpholinone was obtained. After the reaction,Add 15 mL of water to the reaction vessel.And add a small amount of ammonia water to adjust the pH to neutral.Produce a large amount of precipitate, wash it by suction,After drying, it was recrystallized from acetone to give 4-(4-aminophenyl)-3-morpholinone.The yield is 81% |
69% | With sulfuric acid; nitric acid; In sulfolane; at -5 - 30℃; for 2h; | In a three-necked flask a compound obtain according to a.) (500 g, 2.824 mol ) was introduced at temperature 10 0C in4 portions into of concentrated sulphuric acid (IL) within 30minutes . The mixture was then heated to 30 0C for 30 min- utes. The solution is cooled to -5 0C and admixed within one hour with 65% nitric acid ( 205ml ,0.98 eq ) . The mixture was stirred at -5 0C for one hour. Then the mixture was put into ice-water (2.5kg), the precipitate was filtered and washed by water (0.5L*2). 1300 mL of water are metered into the filter at 10 0C, with 25% aqueous ammonia solution (20OmL) . The suspension is admixed with 7L of acetone and heated to 50 0C. Furtheron, the phases were be separated; 12L of acetone/water mixture were distilled of which the product precipitates out. The suspension was cooled to 10 0C and stirred for a further 30 minutes, and the product was isolated. The moist product wass washed with 40OmL of cold acetone and dried at 50 0C un- der reduced pressure to obtain a 432 g of the product (Yield 69 %) |
With sulfuric acid; nitric acid; at 0 - 5℃; for 2.5h; | 150 ml Cone. Sulfuric acid and 100 gm 4-phenyl morpholine-3-one of Formula (A) were added to RBF at 25C to 35C followed by cooling to 0C to 5C and stirring for 15 min. Further, 56.92 gm Nitric Acid (strength 70%) was added over a period of 90 min. and stirred for 60 min. at 0C to 5C. To another RBF 1.5 L process water was added at 25C to 35C and cooled to 0C to 5C. The reaction mass was added to RBF containing water at 0C to 5C and stirred for 60 min. The product was filtered and washed with 2 x 100 ml water to afford the title compound as 4-(4- Nitrophenyl)morpholin-3-one (B). | |
150 ml Conc. Sulfuric acid and 100 gm 4-phenyl morpholine-3-one of Formula (A) were added to RBF at 25 C. to 35 C. followed by cooling to 0 C. to 5 C. and stirring for 15 min. Further, 56.92 gm Nitric Acid (strength 70%) was added over a period of 90 min. and stirred for 60 min. at 0 C. to 5 C. To another RBF 1.5 L process water was added at 25 C. to 35 C. and cooled to 0 C. to 5 C. The reaction mass was added to RBF containing water at 0 C. to 5 C. and stirred for 60 min. The product was filtered and washed with 2*100 ml water to afford the title compound as 4-(4-Nitrophenyl)morpholin-3-one (B). | ||
With sulfuric acid; nitric acid; at 60℃; for 3h; | In a 250 mL round bottom flask, H2SO4 (0.03 mol) was taken and cooled to 0 C. To this HNO 3(0.03 mol) was added in a drop-wise manner [12]. To thisnitrating mixture INT-b (0.01 mole) was added portion wise.After completion of the addition, reaction mixture was stirredat 60 C for 3 h reaction mixture was cooled and quince in icewater, after the confirm on TLC that reaction was completed(Scheme-I). |
Tags: 446292-04-2 synthesis path| 446292-04-2 SDS| 446292-04-2 COA| 446292-04-2 purity| 446292-04-2 application| 446292-04-2 NMR| 446292-04-2 COA| 446292-04-2 structure
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