[ CAS No. 1873-59-2 ] {[proInfo.proName]}

Name: 1873-59-2|4-Hydroxy-3-methylquinolin-2(1H)-one|97%
Brand: Ambeed
SKU: A105077
Price: 40.0 USD
Availability: InStock
Rating: 99 (26 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 1873-59-2

Structure of 1873-59-2 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 1873-59-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1873-59-2 ]

SDS Specification

Alternatived Products of [ 1873-59-2 ]

Product Details of [ 1873-59-2 ]

CAS No. :	1873-59-2	MDL No. :	MFCD00100774
Formula :	C₁₀H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UQAOPJGHDFCPDK-UHFFFAOYSA-N
M.W :	175.18	Pubchem ID :	54678416
Synonyms :

Calculated chemistry of [ 1873-59-2 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.1
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	51.56
TPSA :	53.09 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.58
Log Po/w (XLOGP3) :	1.07
Log Po/w (WLOGP) :	1.54
Log Po/w (MLOGP) :	1.34
Log Po/w (SILICOS-IT) :	2.55
Consensus Log Po/w :	1.62

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.17
Solubility :	1.19 mg/ml ; 0.00677 mol/l
Class :	Soluble
Log S (Ali) :	-1.78
Solubility :	2.93 mg/ml ; 0.0167 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.42
Solubility :	0.0671 mg/ml ; 0.000383 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.54

Safety of [ 1873-59-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1873-59-2 ]

* 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.

Upstream synthesis route of [ 1873-59-2 ]
Downstream synthetic route of [ 1873-59-2 ]

[ 1873-59-2 ] Synthesis Path-Upstream 1~10

1
[ 62-53-3 ]
[ 609-08-5 ]
[ 1873-59-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	at 220 - 270℃;	General procedure: A mixture of the appropriate aniline (100mmol) and substituted diethyl malonate (102mmol) was heated in a flask equipped with distillation head on a metal bath at 220–230°C for 1h and then at 260–270°C until the distillation of ethanol stopped (3–6h). With the exception of preparation of 1f, l, m, the hot liquid reaction mixture was carefully poured into stirred toluene (50mL), cooled down to room temperature and the precipitate was collected by filtration. In the case of 1f, l, m, the hot reaction mixture solidified and it was cooled down to room temperature. The above precipitate or solidified material was mixed with aqueous sodium hydroxide solution (0.5M, 250mL) and toluene (50mL). The substance that remained undissolved (in the preparation of 1c and 1m) was removed by filtration, purified by recrystallization and identified as propanediamide derivatives (1c′ and 1m′, respectively). The layers of the filtrate were separated and the aqueous layer was washed with toluene (2×40mL). The water layer was treated with decolorizing charcoal, filtered and then acidified with 10percent HCl to Congo red. The precipitated hydroxyquinolone 1 was collected by filtration, washed with water, and if necessary, purified by recrystallization.

Reference： [1] Tetrahedron, 2013, vol. 69, # 51, p. 10826 - 10835
[2] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 491 - 500

2
[ 15601-92-0 ]
[ 1873-59-2 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 9, p. 2124 - 2127

3
[ 1399323-75-1 ]
[ 1873-59-2 ]
[ 1399324-65-2 ]

Reference： [1] Helvetica Chimica Acta, 2012, vol. 95, # 8, p. 1352 - 1372

4
[ 524-14-1 ]
[ 1873-59-2 ]

Reference： [1] Organic Letters, 2006, vol. 8, # 26, p. 6063 - 6065

5
[ 55567-59-4 ]
[ 1873-59-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 3041 - 3047

6
[ 862255-44-5 ]
[ 1873-59-2 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1991, vol. 27, # 11, p. 1237 - 1238[2] Khimiya Geterotsiklicheskikh Soedinenii, 1991, # 11, p. 1533 - 1534

7
[ 87-25-2 ]
[ 1873-59-2 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1991, vol. 27, # 11, p. 1237 - 1238[2] Khimiya Geterotsiklicheskikh Soedinenii, 1991, # 11, p. 1533 - 1534

8
[ 529-89-5 ]
[ 1873-59-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 3041 - 3047

9
[ 609-08-5 ]
[ 87-25-2 ]
[ 1873-59-2 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1994, vol. 30, # 5, p. 591 - 595[2] Khimiya Geterotsiklicheskikh Soedinenii, 1994, # 5, p. 673 - 678

10
[ 1264-45-5 ]
[ 1873-59-2 ]

Reference： [1] Organic Letters, 2006, vol. 8, # 26, p. 6063 - 6065

[ 1873-59-2 ] Synthesis Path-Downstream 1~54

2
[ 108-05-4 ]
[ 1873-59-2 ]
[ 76679-25-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 3150 - 3152

3
[ 1873-59-2 ]
[ 144603-20-3 ]

Reference： [1]Monatshefte fur Chemie,1992,vol. 123,p. 617 - 636
[2]Molecules,2018,vol. 23

4
[ 1873-59-2 ]
3-Hydroxy-3-methyl-1,2,3,4-tetrahydrochinolin-2,4-dion [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With peracetic acid; sodium hydroxide; In water; acetic acid; for 0.5h;	General procedure: To a solution of the appropriate 4-hydroxyquinolin-2(1H)-one (1, 20mmol) in aqueous sodium hydroxide solution (0.5M, 20mL), peroxyacetic acid (32-36wt.% in dilute acetic acid, 20mL, 100mmol) was added dropwise under stirring during 30min. The precipitate was collected by filtration and washed with small portions of 5% aqueous potassium carbonate solution until the filter cake is free of potentially unreacted starting material 1 (until the filtrate is not clear solution upon acidificationwith conc. hydrochloric acid). Then the solid was washed with water (3×30mL), air dried and recrystallized from the appropriate solvent. Analytical and spectral data of 3-hydroxyquinoline-2,4(1H,3H)-diones 2 are given below.

Reference： [1]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 1535 - 1540
[2]Tetrahedron,2013,vol. 69,p. 10826 - 10835
[3]Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie,1982,vol. 37,p. 1196 - 1200

5
[ 1873-59-2 ]
3-methyl-3-nitroquinoline-2,4-(1H,3H)-dione [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 1535 - 1540

6
[ 55567-59-4 ]
[ 1873-59-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3041 - 3047

7
[ 862255-44-5 ]
[ 1873-59-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1991,vol. 27,p. 1237 - 1238
Khimiya Geterotsiklicheskikh Soedinenii,1991,p. 1533 - 1534

8
[ 1873-59-2 ]
[ 107-13-1 ]
[ 76679-24-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 3150 - 3152

9
[ 1873-59-2 ]
[ 115-11-7 ]
[ 76679-22-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 3150 - 3152

10
[ 609-08-5 ]
[ 87-25-2 ]
[ 1873-59-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1994,vol. 30,p. 591 - 595
Khimiya Geterotsiklicheskikh Soedinenii,1994,p. 673 - 678

11
[ 1873-59-2 ]
3-Bromo-3-methyl-1H-quinoline-2,4-dione [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1995,vol. 31,p. 176 - 179
Khimiya Geterotsiklicheskikh Soedinenii,1995,p. 204 - 207

13
[ 1873-59-2 ]
[ 541-47-9 ]
[ 523-64-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2003,vol. 42,p. 187 - 188

14
[ 530-48-3 ]
[ 1873-59-2 ]
4,4a,6,10b-tetrahydro-10b-hydroxy-3,3-diphenyl-4a-methyl-1,2-dioxino[4,3-c]quinolin-5(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With manganese(III) triacetate dihydrate; In acetic acid; at 23℃; for 15.0h;	General procedure: 4.3 Mn(III)-catalyzed aerobic oxidation of a mixture of alkenes 2 and 4-hydroxyquinolin-2(1H)-ones To a mixture of 1,1-diphenylethene 1 (Ar1=Ar2=Ph) (179.0 mg; 1 mmol) and quinolinone 2 (R=Me) (362.7 mg; 2.1 mmol) in glacial acetic acid (25 mL), Mn(OAc)3·2H2O (131.9 mg; 0.53 mmol) was added. The mixture was stirred at 23 C in air for 4 h, and then the reaction was quenched by adding water (40 mL) to the reaction mixture. The aqueous solution was extracted five times with CH2Cl2 (10 mL*5) and the combined extracts were washed twice with water, a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was separated by silica gel flash column chromatography eluting with CH2Cl2/hexane (7:3 v/v), giving bis(hydroperoxide) 3a (210.1 mg; 71% yield based on the alkene 1 used) 4.3.19 4,4a,6,10b-Tetrahydro-10b-hydroxy-3,3-diphenyl-4a-methyl-1,2-dioxino[4,3-c]quinolin-5(3H)-one (7a: R=Me, Ar=Ph) Colorless microcrystals (from CH2Cl2/hexane), mp 195 C (decomp.). IR (KBr): nu 3382-2929 (OH and NH), 1678 (C=O) cm-1. 1H NMR (300 MHz, CDCl3): delta 10.1 (1H, s, NH), 7.73-7.70 (1H, m, arom H), 7.57 (1H, br s, arom H), 7.46-7.43 (3H, m, arom H), 7.34-7.01 (8H, m, arom H), 6.77-6.75 (1H, m, arom H), 3.47 (1H, br s, OH), 3.34 (1H, br, HCH), 2.75 (1H, d, J=13.5 Hz, HCH), 1.10 (3H, s, Me) ppm. 13C NMR (75 MHz, CDCl3): delta 171.2 (C=O), 144.8, 142.0 (2C, arom C), 136.7 (2C, arom C), 130.4 (arom C), 128.0 (4C, arom CH), 127.2 (2C, arom CH), 127.1 (arom C), 127.0 (2C, arom CH), 126.3 (arom CH), 125.4 (2C, arom CH), 122.0 (arom CH), 99.0 (C-10b), 84.4 (C-3), 44.0 (C-4a), 30.3 (CH2), 22.3 (Me) ppm. Anal. Calcd for C24H21NO4: C, 74.40; H, 5.46; N, 3.62. Found: C, 74.20; H, 5.41; N, 3.59.

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 703 - 706
[2]Tetrahedron,2014,vol. 70,p. 1437 - 1450

15
[ 1873-59-2 ]
[ 2919-20-2 ]
4,4a,6,10b-tetrahydro-10b-hydroxy-3,3-bis(4-methylphenyl)-4a-methyl-1,2-dioxino[4,3-c]quinolin-5(3H)-one [ No CAS ]
3-[2-hydroperoxy-2,2-bis(4-methylphenylethyl)]-3-methylquinoline-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%; 58%	With manganese(III) triacetate dihydrate; In acetic acid; at 23℃; for 15.0h;	General procedure: 4.3 Mn(III)-catalyzed aerobic oxidation of a mixture of alkenes 2 and 4-hydroxyquinolin-2(1H)-ones To a mixture of 1,1-diphenylethene 1 (Ar1=Ar2=Ph) (179.0 mg; 1 mmol) and quinolinone 2 (R=Me) (362.7 mg; 2.1 mmol) in glacial acetic acid (25 mL), Mn(OAc)3·2H2O (131.9 mg; 0.53 mmol) was added. The mixture was stirred at 23 C in air for 4 h, and then the reaction was quenched by adding water (40 mL) to the reaction mixture. The aqueous solution was extracted five times with CH2Cl2 (10 mL*5) and the combined extracts were washed twice with water, a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was separated by silica gel flash column chromatography eluting with CH2Cl2/hexane (7:3 v/v), giving bis(hydroperoxide) 3a (210.1 mg; 71% yield based on the alkene 1 used)

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 703 - 706
[2]Tetrahedron,2014,vol. 70,p. 1437 - 1450

16
[ 1873-59-2 ]
[ 2642-81-1 ]
3,3-bis(4-chlorophenyl)-4,4a,6,10b-tetrahydro-10b-hydroxy-4a-methyl-1,2-dioxino[4,3-c]quinolin-5(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With manganese(III) triacetate dihydrate; In acetic acid; at 23℃; for 18.0h;	General procedure: 4.3 Mn(III)-catalyzed aerobic oxidation of a mixture of alkenes 2 and 4-hydroxyquinolin-2(1H)-ones To a mixture of 1,1-diphenylethene 1 (Ar1=Ar2=Ph) (179.0 mg; 1 mmol) and quinolinone 2 (R=Me) (362.7 mg; 2.1 mmol) in glacial acetic acid (25 mL), Mn(OAc)3·2H2O (131.9 mg; 0.53 mmol) was added. The mixture was stirred at 23 C in air for 4 h, and then the reaction was quenched by adding water (40 mL) to the reaction mixture. The aqueous solution was extracted five times with CH2Cl2 (10 mL*5) and the combined extracts were washed twice with water, a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was separated by silica gel flash column chromatography eluting with CH2Cl2/hexane (7:3 v/v), giving bis(hydroperoxide) 3a (210.1 mg; 71% yield based on the alkene 1 used) 4.3.23 3,3-Bis(4-chlorophenyl)-4,4a,6,10b-tetrahydro-10b-hydroxy-4a-methyl-1,2-dioxino[4,3-c]quinolin-5(3H)-one (7e: R=Me, Ar=4-Cl-C6H4) Pale yellow microcrystals (from MeOH), mp 155-157 C. IR (KBr): nu 3400-3060 (OH), 3300-2900 (NH), 1678 (C=O) cm-1. 1H NMR (300 MHz, CDCl3): delta 10.0 (1H, s, NH), 7.85-7.76 (1H, m, arom H), 7.49-6.89 (10H, m, arom H), 6.79-6.77 (1H, m, arom H), 5.45 (1H, s, OH), 3.54 (1H, d, J=13.1 Hz, HCH), 2.78 (1H, d, J=13.1 Hz, HCH), 1.15 (3H, s, Me) ppm. 13C NMR (75 MHz, CDCl3): delta 170.2 (C=O), 141.6 (arom C), 139.0 (2C, arom C), 135.6 (arom C), 130.5 (2C, arom C), 129.3 (2C, arom CH), 128.0 (C-5), 126.9 (2C, arom CH), 126.2 (2C, arom CH), 126.1 (arom CH), 125.8 (2C, arom CH), 122.3 (arom CH), 114.8 (arom CH), 98.0 (C-10b), 83.1 (C-3), 52.6 (C-4a), 43.0 (CH2), 21.4 (Me) ppm. FAB HRMS (acetone/NBA): calcd for C24H20Cl2NO4 456.0769 (M+H); found 456.0779.

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 703 - 706
[2]Tetrahedron,2014,vol. 70,p. 1437 - 1450

17
[ 530-48-3 ]
[ 1873-59-2 ]
3-methyl-3-(2,2-diphenylethenyl)quinoline-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With manganese(III) triacetate dihydrate; In acetic acid; for 30.0h;Reflux;	General procedure: 4.5 Mn(III)-mediated oxidation of alkenes in the presence of 4-hydroxyquinolin-2(1H)-ones and the related substrates at reflux temperature (0042) A mixture of 1,1-diphenylethene 1 (Ar=Ph) (181.3mg; 1mmol), 4-hydroxy-2-quinolinone 2 (R=Me, X=H) (351.4mg; 2mmol), and Mn(OAc)3·2H2O (814.4mg; 3mmol) in glacial acetic acid (25mL) was heated under reflux until the brown color of Mn(III) disappeared (normally for 3min). The solvent was removed in vacuo and water (25mL) was added to the reaction mixture. The aqueous solution was then extracted three times with dichloromethane (20mL). The combined extracts were washed with a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate, and then concentrated to dryness. The residue was separated on silica gel TLC developed with 5% methanol/dichloromethane, giving the products 9a (310.6mg; 87%) and 10a (23.6mg; 7%) (Table 3, entry 2). Molar ratio and reaction times of other oxidation are shown in Tables 3-5. The products were further purified by recrystallization from an appropriate solvent for the analytical sample, and their physical data are given below.

Reference： [1]Heterocyclic Communications,2004,vol. 10,p. 135 - 138
[2]Tetrahedron,2014,vol. 70,p. 1437 - 1450

18
[ 530-48-3 ]
[ 1873-59-2 ]
3,3a,5,9b-tetrahydro-9b-hydroxy-3a-methyl-2,2-diphenylfuro[3,2-c]quinolin-4(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With copper diacetate; manganese(III) triacetate dihydrate; In acetic acid; at 23℃; for 3.5h;	General procedure: 4.5 Mn(III)-mediated oxidation of alkenes in the presence of 4-hydroxyquinolin-2(1H)-ones and the related substrates at reflux temperature (0042) A mixture of 1,1-diphenylethene 1 (Ar=Ph) (181.3mg; 1mmol), 4-hydroxy-2-quinolinone 2 (R=Me, X=H) (351.4mg; 2mmol), and Mn(OAc)3·2H2O (814.4mg; 3mmol) in glacial acetic acid (25mL) was heated under reflux until the brown color of Mn(III) disappeared (normally for 3min). The solvent was removed in vacuo and water (25mL) was added to the reaction mixture. The aqueous solution was then extracted three times with dichloromethane (20mL). The combined extracts were washed with a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate, and then concentrated to dryness. The residue was separated on silica gel TLC developed with 5% methanol/dichloromethane, giving the products 9a (310.6mg; 87%) and 10a (23.6mg; 7%) (Table 3, entry 2). Molar ratio and reaction times of other oxidation are shown in Tables 3-5. The products were further purified by recrystallization from an appropriate solvent for the analytical sample, and their physical data are given below.

Reference： [1]Heterocyclic Communications,2004,vol. 10,p. 135 - 138
[2]Tetrahedron,2014,vol. 70,p. 1437 - 1450

19
[ 1873-59-2 ]
[ 2919-20-2 ]
3-[2,2-bis(4-methylphenyl)ethenyl]-3-methylquinoline-2,4(1H,3H)-dione [ No CAS ]

Reference： [1]Heterocyclic Communications,2004,vol. 10,p. 135 - 138

20
[ 1873-59-2 ]
[ 2642-81-1 ]
3-[2,2-bis(4-chlorophenyl)ethenyl]-3-methylquinoline-2,4(1H,3H)-dione [ No CAS ]
2,2-bis(4-chlorophenyl)-3,3a,5,9b-tetrahydro-9b-hydroxy-3a-methylfuro[3,2-c]quinolin-4(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%; 35%	With manganese(III) triacetate dihydrate; In acetic acid; for 2.0h;Reflux;	General procedure: 4.5 Mn(III)-mediated oxidation of alkenes in the presence of 4-hydroxyquinolin-2(1H)-ones and the related substrates at reflux temperature (0042) A mixture of 1,1-diphenylethene 1 (Ar=Ph) (181.3mg; 1mmol), 4-hydroxy-2-quinolinone 2 (R=Me, X=H) (351.4mg; 2mmol), and Mn(OAc)3·2H2O (814.4mg; 3mmol) in glacial acetic acid (25mL) was heated under reflux until the brown color of Mn(III) disappeared (normally for 3min). The solvent was removed in vacuo and water (25mL) was added to the reaction mixture. The aqueous solution was then extracted three times with dichloromethane (20mL). The combined extracts were washed with a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate, and then concentrated to dryness. The residue was separated on silica gel TLC developed with 5% methanol/dichloromethane, giving the products 9a (310.6mg; 87%) and 10a (23.6mg; 7%) (Table 3, entry 2). Molar ratio and reaction times of other oxidation are shown in Tables 3-5. The products were further purified by recrystallization from an appropriate solvent for the analytical sample, and their physical data are given below.

Reference： [1]Heterocyclic Communications,2004,vol. 10,p. 135 - 138
[2]Tetrahedron,2014,vol. 70,p. 1437 - 1450

21
anthraniloyl-S-CoA thioester [ No CAS ]
[ 524-14-1 ]
[ 1873-59-2 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 6063 - 6065

22
anthraniloyl-S-CoA thioester [ No CAS ]
[ 1264-45-5 ]
[ 1873-59-2 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 6063 - 6065

23
[ 1873-59-2 ]
[ 76679-27-1 ]

Reference： [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 3150 - 3152

24
[ 1873-59-2 ]
[ 76679-26-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 3150 - 3152

25
[ 87-25-2 ]
[ 1873-59-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1991,vol. 27,p. 1237 - 1238
Khimiya Geterotsiklicheskikh Soedinenii,1991,p. 1533 - 1534

26
[ 529-89-5 ]
[ 1873-59-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3041 - 3047

27
[ 15601-92-0 ]
[ 1873-59-2 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2124 - 2127

28
[ 1399323-75-1 ]
[ 1873-59-2 ]
[ 1399324-65-2 ]

Reference： [1]Helvetica Chimica Acta,2012,vol. 95,p. 1352 - 1372

29
[ 1873-59-2 ]
[ 505-14-6 ]
[ 1399323-75-1 ]

Reference： [1]Helvetica Chimica Acta,2012,vol. 95,p. 1352 - 1372

30
[ 1873-59-2 ]
[ 1430330-16-7 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2124 - 2127

31
[ 1873-59-2 ]
[ 1430330-14-5 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2124 - 2127

32
[ 1873-59-2 ]
(E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-3-methylquinolin-4(1H)-one [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2124 - 2127

33
[ 1873-59-2 ]
C₂₂H₂₆N₂OS [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2124 - 2127

34
[ 1873-59-2 ]
[ 1430330-15-6 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2124 - 2127

35
[ 1873-59-2 ]
[ 18162-48-6 ]
[ 1430330-13-4 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2124 - 2127

36
[ 530-48-3 ]
[ 1873-59-2 ]
3-methyl-3-(2,2-diphenylethenyl)quinoline-2,4(1H,3H)-dione [ No CAS ]
3,3a,5,9b-tetrahydro-9b-hydroxy-3a-methyl-2,2-diphenylfuro[3,2-c]quinolin-4(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%; 48%	With manganese(III) triacetate dihydrate; In acetic acid; for 2.5h;Reflux;	General procedure: 4.5 Mn(III)-mediated oxidation of alkenes in the presence of 4-hydroxyquinolin-2(1H)-ones and the related substrates at reflux temperature (0042) A mixture of 1,1-diphenylethene 1 (Ar=Ph) (181.3mg; 1mmol), 4-hydroxy-2-quinolinone 2 (R=Me, X=H) (351.4mg; 2mmol), and Mn(OAc)3·2H2O (814.4mg; 3mmol) in glacial acetic acid (25mL) was heated under reflux until the brown color of Mn(III) disappeared (normally for 3min). The solvent was removed in vacuo and water (25mL) was added to the reaction mixture. The aqueous solution was then extracted three times with dichloromethane (20mL). The combined extracts were washed with a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate, and then concentrated to dryness. The residue was separated on silica gel TLC developed with 5% methanol/dichloromethane, giving the products 9a (310.6mg; 87%) and 10a (23.6mg; 7%) (Table 3, entry 2). Molar ratio and reaction times of other oxidation are shown in Tables 3-5. The products were further purified by recrystallization from an appropriate solvent for the analytical sample, and their physical data are given below.

Reference： [1]Tetrahedron,2014,vol. 70,p. 1437 - 1450

37
[ 62-53-3 ]
[ 609-08-5 ]
[ 1873-59-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	at 220 - 270℃;	General procedure: A mixture of the appropriate aniline (100mmol) and substituted diethyl malonate (102mmol) was heated in a flask equipped with distillation head on a metal bath at 220-230C for 1h and then at 260-270C until the distillation of ethanol stopped (3-6h). With the exception of preparation of 1f, l, m, the hot liquid reaction mixture was carefully poured into stirred toluene (50mL), cooled down to room temperature and the precipitate was collected by filtration. In the case of 1f, l, m, the hot reaction mixture solidified and it was cooled down to room temperature. The above precipitate or solidified material was mixed with aqueous sodium hydroxide solution (0.5M, 250mL) and toluene (50mL). The substance that remained undissolved (in the preparation of 1c and 1m) was removed by filtration, purified by recrystallization and identified as propanediamide derivatives (1c? and 1m?, respectively). The layers of the filtrate were separated and the aqueous layer was washed with toluene (2×40mL). The water layer was treated with decolorizing charcoal, filtered and then acidified with 10% HCl to Congo red. The precipitated hydroxyquinolone 1 was collected by filtration, washed with water, and if necessary, purified by recrystallization.
	at 220 - 270℃;	General procedure: Compounds 1-24, 26e-32 and 36-38 were synthesized by a modified literature procedure [13]. A mixture of the appropriate aniline (100 mmol) and substituted diethyl malonate (102-105 mmol) was heated on a metal bath at 220-230 C for 1 hand then at 260-270 C for 3-6 h (the reaction was complete when the distillation of evolving ethanol stopped). After cooling, the solid product was crushed, dissolved in aqueous sodium hydroxide solution (0.5 M, 250 mL) and after filtration the filtrate was washed three times with toluene (40 mL). The aqueous layer was filtered and the product was precipitated from alkaline water layer with concentrated hydrochloric acid. The resulting pure 4-hydroxyquinolin-2(1H)-one product was collected by filtration and washed with water. For the analytical purposes and biological screenings, the crude products were recrystallized from the solvent indicated below.

Reference： [1]Tetrahedron,2013,vol. 69,p. 10826 - 10835
[2]European Journal of Medicinal Chemistry,2017,vol. 138,p. 491 - 500

38
[ 1873-59-2 ]
[ 14469-11-5 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 10826 - 10835

39
[ 1873-59-2 ]
[ 108-24-7 ]
3-methyl-2-oxo-1,2-dihydroquinolin-4-yl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridine; at 20℃;	General procedure: Acetic anhydride (30 mL, 0.31 mol) was added dropwise to a solution of an appropriate 4-hydroxyquinolin-2(1H)-one (15.0 mmol) in pyridine (45 mL, 0.55 mol) within 10 min. The reaction mixture was stirred at room temperature until TLC indicated complete consumption of the starting material (30-120 min). The resulting suspension was evaporated in vacuo to dryness. The residue was triturated with water (50 mL), and the resulting precipitate was collected by filtration. The filter cake was washed with water until the filtrate was neutral and crystallized from a suitable solvent affording pure product (40-50).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 138,p. 491 - 500

40
[ 1873-59-2 ]
3-methyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-1-(prop-2-yn-1-yl)quinoline-2,4(1H,3H)-dione [ No CAS ]

Reference： [1]Molecules,2018,vol. 23
[2]Molecules,2018,vol. 23

41
[ 1873-59-2 ]
(1-(3-methyl-2,4-dioxo-1-(prop-2-yn-1-yl)-1,2,3,4-tetrahydroquinolin-3-yl)-1H-1,2,3-triazol-4-yl)methyl acetate [ No CAS ]