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Chemical Structure| 694-85-9 Chemical Structure| 694-85-9

Structure of 1-Methyl-2-pyridone
CAS No.: 694-85-9

Chemical Structure| 694-85-9

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Product Details of [ 694-85-9 ]

CAS No. :694-85-9
Formula : C6H7NO
M.W : 109.13
SMILES Code : CN1C=CC=CC1=O
MDL No. :MFCD00006520
InChI Key :DVVGIUUJYPYENY-UHFFFAOYSA-N
Pubchem ID :12755

Safety of [ 694-85-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 694-85-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 31.96
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

22.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.56
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.23
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.39
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.59
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.96
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.65

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.93
Solubility 12.9 mg/ml ; 0.118 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

0.23
Solubility 183.0 mg/ml ; 1.68 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.43
Solubility 4.06 mg/ml ; 0.0372 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.13 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.15

Application In Synthesis of [ 694-85-9 ]

* 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.

  • Downstream synthetic route of [ 694-85-9 ]

[ 694-85-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 694-85-9 ]
  • [ 93222-42-5 ]
  • [ 121463-31-8 ]
  • 2
  • [ 694-85-9 ]
  • [ 32896-90-5 ]
  • [ 14150-94-8 ]
  • 3
  • [ 694-85-9 ]
  • [ 14150-94-8 ]
YieldReaction ConditionsOperation in experiment
30% With sulfuric acid; nitric acid; at 100℃; To a stirred mixture of 1-METHYL-LH-PYRIDIN-2-ONE (33.47 g, 0.306 mol) and concentrated H2S04 (300 ML) at 100 C was added concentrated HNO3 (120 mL) in portions. The reaction mixture was heated at this temperature overnight, and then poured into ice (1400 mL). The precipitate was filtered off and washed with water to give the title compound (Yield: 18.66 g, 30%). LH NMR (400 MHZ, CDCl3) : 8 9.05 (d, 1H), 8.90 (d, 1H), 3.80 (s, 3H).
28% With sulfuric acid; nitric acid; 1-Methyl-3,5-dinitro-2-pyridone 1-Methyl-2-pyridone (25.0 g, 0.229 mol) was added to sulfuric acid (500 mL) at 0 C. After stirring for 5 min., nitric acid (200 mL) was added dropwise at 0 C. After addition, the reaction temperature was slowly raised to 100 C., and then maintained for 5 h. The reaction mixture was poured into ice, basified with potassium carbonate to pH 8 and extracted with CH2Cl2 (100 mL*3). The combined organic layers were dried over Na2SO4 and concentrated to yield 1-methyl-3,5-dinitro-2-pyridone (12.5 g, 28%), which was used without further purification.
28% With sulfuric acid; nitric acid; at 0 - 100℃; for 5h; 1-Methyl-2-pyridone (25.0 g, 0.229 mol) was added to sulfuric acid (500 mL) at 0 C. After stirring for 5 min., nitric acid (200 mL) was added dropwise at 0 C. After addition, the reaction temperature was slowly raised to 100 C., and then maintained for 5 h. The reaction mixture was poured into ice, basified with potassium carbonate to pH 8 and extracted with CH2Cl2 (100 mL*3). The combined organic layers were dried over Na2SO4 and concentrated to yield 1-methyl-3,5-dinitro-2-pyridone (12.5 g, 28%), which was used without further purification.
22% With sulfuric acid; nitric acid; at 100℃; for 4h; Step 1: To a solution of N-methylpyridinone (A) (3 g, 27.49 mmol) in H2SO4 (100 mL) was slowly added HNO3 (60 %) (0.3 mL, 137.45 mmol) at room temperature. The reaction mixture was heated to 100 C for 4 h. TLC showed complete consumption of starting material. The reaction mixture was cooled to room temperature and neutralized with NaHCO3. The mixture was extracted with ethyl acetate and washed with water and brine. The extract was dried over MgSO4 and concentrated under reduced pressure to give 1-methyl-3,5-dinitropyridin-2(1H)-one (B) (1.19 g, 22 %)
22% With sulfuric acid; nitric acid; at 20 - 100℃; To a solution of N-methylpyridinone (A) (3 g, 27.49 mmol) in H2SO4 (100 mL) was slowly added HNO3 (60%) (0.3 mL, 137.45 mmol) at room temperature. The reaction mixture was heated to 100 C. for 4 h. TLC showed complete consumption of starting material. The reaction mixture was cooled to room temperature and neutralized with NaHCO3. The mixture was extracted with ethyl acetate and washed with water and brine. The extract was dried over MgSO4 and concentrated under reduced pressure to give 1-methyl-3,5-dinitropyridin-2(1H)-one (B) (1.19 g, 22%)
With sulfuric acid; nitric acid; at 5 - 150℃; for 16h; l-Methyl-lH-pyridin-2-one (6.67 g, 61.2 mmol) was added drop wise to H2SO4 (30 mL) keeping the temperature between 0-5 0C. HNO3 (19.3 g, 612 mmol) was added drop wise to above maintaining the temperature below 5 0C. After all HNO3 was added, the temperature was raised slowly to 150 0C and the reaction was ran for 16 h. The mixture was cooled to RT and poured into ice. The resultant yellow precipitate was filtered and dried under reduced pressure, affording l-methyl-3,5-dinitro-lH-pyridin-2-one as yellow solid.

  • 4
  • [ 694-85-9 ]
  • [ 1095-03-0 ]
  • [ 13180-21-7 ]
  • 5
  • [ 694-85-9 ]
  • [ 802919-90-0 ]
  • 3-(difluoro(phenylsulfonyl)methyl)-1-methylpyridin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With tris[2-phenylpyridinato-C2,N]iridium(III); sodium thiosulfate; In acetonitrile; at 20℃; for 6h;Irradiation; Inert atmosphere; General procedure: The reaction of 1a with 2ais representative (Table 1, entry 1). Ir(ppy)3 (3.3 mg, 0.0050 mmol) was placed in a Schlenk tube.Nitrogen gas displacement was done by using the standard Schlenk technique, and N-methyl-2-pyridone(1a, 136.4 mg, 1.25 mmol) and ethyl bromodifluoroacetate (2a, 50.7 mg, 0.25 mmol) were added usingsyringe followed by addition of MeCN (3 mL). The mixture was stirred for 6 h under blue light LEDirradiation (12 DC/3 W). Water (20 mL) was added, and extraction was done with EtOAc (15 mL x 3).The combined organic phase was dried over sodium sulfate and then concentrated in vacuo. Purificationvia column chromatography (Wakosil C-200, hexane/EtOAc = 20/1 to EtOAc/CH2Cl2/Et3N = 1/1/0.05)provided pure ethyl 2,2-difluoro-2-(1-methyl-2-oxo-1,2-dihydropyridin-3-yl)acetate (3aa, 42.7 mg, 0.19mmol, 74% yield).
  • 6
  • [ 694-85-9 ]
  • [ 73183-34-3 ]
  • [ 1002309-52-5 ]
  • 7
  • [ 694-85-9 ]
  • [ 73183-34-3 ]
  • [ 1002309-52-5 ]
  • C18H29B2NO5 [ No CAS ]
  • 8
  • [ 694-85-9 ]
  • [ 14135-38-7 ]
  • 5-((2-fluorophenyl)thio)-1-methylpyridin-2(1H)-one [ No CAS ]
 

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