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Chemical Structure| 1198-97-6 Chemical Structure| 1198-97-6

Structure of 4-Phenyl-2-pyrrolidinone
CAS No.: 1198-97-6

Chemical Structure| 1198-97-6

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Product Details of [ 1198-97-6 ]

CAS No. :1198-97-6
Formula : C10H11NO
M.W : 161.20
SMILES Code : C2=C(C1CC(=O)NC1)C=CC=C2
MDL No. :MFCD01687226
InChI Key :HOJZEMQCQRPLQQ-UHFFFAOYSA-N
Pubchem ID :121397

Safety of [ 1198-97-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 1198-97-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.3
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 50.63
TPSA ?

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

29.1 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.63
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

1.0
Log Po/w (WLOGP)?

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

0.91
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.

1.49
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

2.2
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.45

Water Solubility

Log S (ESOL):?

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

-1.77
Solubility 2.72 mg/ml ; 0.0168 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.

-1.2
Solubility 10.2 mg/ml ; 0.0631 mol/l
Class?

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

Very 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

-3.21
Solubility 0.101 mg/ml ; 0.000624 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

Yes
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.

-6.57 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)

1.55

Application In Synthesis of [ 1198-97-6 ]

* 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 [ 1198-97-6 ]

[ 1198-97-6 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 77519-55-2 ]
  • [ 1198-97-6 ]
YieldReaction ConditionsOperation in experiment
100% In toluene; for 5h;Reflux; General procedure: A suspension of carboxylic acid in toluene was heated to reflux for 5 h. After cooling to roomtemperature, the solvent was evaporated and the pure product was obtained. 1H- and 13C-NMR datafor the compounds ()-2a-c [42], are identical with those described in the literature.
  • 3
  • [ 1078-21-3 ]
  • [ 1198-97-6 ]
  • 4
  • [ 1198-97-6 ]
  • [ 1078-21-3 ]
  • 7
  • [ 1198-97-6 ]
  • [ 368-39-8 ]
  • [ 22349-33-3 ]
  • 8
  • [ 1198-97-6 ]
  • [ 42340-98-7 ]
  • [ 916345-91-0 ]
  • 9
  • [ 1198-97-6 ]
  • [ 96-34-4 ]
  • [ 68497-63-2 ]
YieldReaction ConditionsOperation in experiment
84% the effect of different organic solvents on the reaction yield:9.6 g (0.06 mol) of 4-phenyl-2-pyrrolidone was dissolved in 100 mL of an organic solvent, and the organic solventIn the case of Table 1, the temperature was lowered to the inner temperature of -10 C, and 13.5 g (0.12 mol) of potassium t-butoxide was added in portions, to continue stirring 2h, cooling to the internal temperature -10 ,A solution of 13.0 g (0.12 mol) of methyl chloroacetate was added dropwise and the reaction was continued at -10 to 0 C2h, the reaction was completed, 160 mL of ethyl acetate, 65 mL of saturated ammonium chloride / 65 mL of water were added, stirred and the layers were stirred,2 ethyl acetate extraction 2 times, the organic layer, saturated ammonium chloride 40mL × 2 washed 2 times, 40mL washed 1, 8g anhydrous magnesium sulfate dryDried for 30 min, filtered to give a pale yellow oil, 4-phenyl-2-pyrrolidone-1-acetate,
In tetrahydrofuran; water; mineral oil; (a) Methyl 2-oxo-4-phenylpyrrolidineacetate A total of 8.4 g. of 57% sodium hydride dispersion in mineral oil is washed successively with 200 ml. portions of toluene to remove the mineral oil. The residual sodium hydride is suspended in 600 ml. of tetrahydrofuran and the suspension is treated portionwise, with stirring, with 32.8 g. of <strong>[1198-97-6]4-phenyl-2-pyrrolidinone</strong> (C.A. 53:4253 g.). Upon completion of the addition, the stirred mixture is heated in the range of 35-65 C. from one to three hours (monitoring hydrogen evolution), followed by the dropwise addition of 21.8 g. of methyl chloroacetate. After stirring for about 16 hours at 55-65 C. to insure completeness of reaction, the mixture is cooled and evaporated at reduced pressure. The residue is mixed with 200 ml. of water and extracted twice with 200 ml. portions of ether. The combined ether extract is dried, evaporated and fractionated at reduced pressure. Methyl 2-oxo-4-phenyl-1-pyrrolidineacetate is obtained as an oil, b.p. 158-159 C./0.15 mm.
  • 12
  • [ 1198-97-6 ]
  • [ 106-96-7 ]
  • [ 137518-26-4 ]
  • 15
  • [ 34687-03-1 ]
  • [ 1198-97-6 ]
YieldReaction ConditionsOperation in experiment
l-fer£-Butoxvcarbonvl-3-phenvl-pvrrolidine; A solution of 4-nitro-3"phenyl-butyric acid methyl ester (4.02 g, 18 mmol) and Raney-Nickel (6 ml, slurry in water) in methanol (30 ml) was stirred under hydrogen atmosphere for 3 hours. After filtration using celite and removal of the solvent under reduced pressure, residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine, and then dried over sodium sulfate. The solvents were removed under reduced pressure, and the residue was dissolved in toluene (50 ml) and the resulting solution was refluxed for 6 hours. Removal of the204 <n="206"/>solvent afforded crude 4-phenyl-pyrrolidin-2-one. A solution of crude 4-phenyl-pyrrolidin-2-one in tetrahydrofuran (20 ml) was added to a solution of lithium aluminum hydride (1.34 g, 35.3 mmol) and the mixture was refluxed for 6 hours. After quenching the reaction with 20% aqueous sodium hydroxide, a solution of drtert-butyl dicarbonate (4.14 g, 19 mmol) was added and the mixture was stirred for 3 hours. Aqueous citric acid and aqueous potassium hydrogen sulfate was added to acidify the solution, and the solution was extracted with toluene. The organic layer was washed with water, aqueous sodium bicarbonate, brine, and dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified with silica gel column chromatography (eluent. hexane/ethyl acetate = 9/1) to afford l-zter£-butoxycarbonyl;3-phenyl-pyrrolidine (1.84 g, 42%).
  • 16
  • [ 41441-40-1 ]
  • [ 1198-97-6 ]
YieldReaction ConditionsOperation in experiment
82% With sodium tetrahydroborate; nickel(II) chloride hexahydrate; In ethanol; at 0℃; for 2h; General procedure: Nitroesters 5a-b (1.0 mmol) and NiCl2*6H2O (10.0 mmol) dissolved in 5 mL of ethanol were added into a round bottom flask. The mixture was submitted to magnetic stirring in an ice bath, followed by the addition of NaBH4 (10.0 mmol), and then it was stirred for 2 h at 0 C. Afterwards, 20 mL of NH4Cl was added into the flask and extracted with CHCl3 (3 × 20.0 mL). The organic phases were combined, dried with MgSO4 anhydrous, filtered through Celite and evaporated under vacuum.
  • 17
  • ethyl 4-amino-3-phenylbutanoate hydrochloride [ No CAS ]
  • [ 1198-97-6 ]
  • 19
  • [ 1198-97-6 ]
  • [ 7425-45-8 ]
  • 2-(2-Oxo-4-phenyl-pyrrolidin-1-yl)-butyric acid ethyl ester [ No CAS ]
  • 20
  • [ 1198-97-6 ]
  • [ 105-39-5 ]
  • [ 70291-40-6 ]
  • 1-[(2-oxo-4-phenylpyrrolidin-1-yl)acetyl]-4-phenyl-2-pyrrolidone [ No CAS ]
  • 21
  • [ 1198-97-6 ]
  • [ 535-13-7 ]
  • 2-(2-Oxo-4-phenyl-pyrrolidin-1-yl)-propionic acid ethyl ester [ No CAS ]
  • 24
  • (+-)-3-cyano-3-phenyl-propionic acid ethyl ester [ No CAS ]
  • [ 1198-97-6 ]
  • 25
  • [ 1198-97-6 ]
  • [ 109-70-6 ]
  • 1-(3-chloropropyl)-4-phenyl-2-pyrrolidinone [ No CAS ]
  • 26
  • [ 1198-97-6 ]
  • [ 144-62-7 ]
  • [ 100-35-6 ]
  • 1-(2-diethylaminoethyl)-4-phenyl-2-pyrrolidinone oxalate [ No CAS ]
  • 27
  • [ 3240-94-6 ]
  • [ 1198-97-6 ]
  • [ 144-62-7 ]
  • 1-(2-morpholinoethyl)-4-phenyl-2-pyrrolidinone oxalate [ No CAS ]
  • 28
  • [ 1198-97-6 ]
  • [ 144-62-7 ]
  • [ 109-54-6 ]
  • 1-(3-dimethylaminopropyl)-4-phenyl-2-pyrrolidinone oxalate [ No CAS ]
  • 29
  • [ 1198-97-6 ]
  • [ 22349-30-0 ]
  • 30
  • [ 1198-97-6 ]
  • [ 71657-88-0 ]
  • [ 62624-45-7 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide; carbon dioxide; In methanol;Supercritical conditions; Resolution of racemate; 4-Phenyl-pyiTolidin-2-one (commercial) was separated by SFC (Chiralpak AD column; eluting with C02/MeOH (0.2% NH4OH) =75/25)) to afford the title compound as the second eluting isomer.
  • 31
  • 4-nitro-3-phenylbutanoic acid polyglyceryl ester [ No CAS ]
  • [ 1198-97-6 ]
  • 32
  • [ 866789-27-7 ]
  • [ 1198-97-6 ]
  • 34
  • [ 1198-97-6 ]
  • 4,7-diphenyl-7,8-dihydro-6<i>H</i>-pyrrolo[1,2-<i>a</i>]pyrimidin-2-ylideneamine [ No CAS ]
  • 35
  • [ 1198-97-6 ]
  • 2,7-diphenyl-7,8-dihydro-6<i>H</i>-pyrrolo[1,2-<i>a</i>]pyrimidin-4-ylideneamine [ No CAS ]
 

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