[ CAS No. 16619-14-0 ] {[proInfo.proName]}

Name: 16619-14-0|2-Phenyl-2,3-dihydroquinolin-4(1H)-one|97%
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SKU: A208103
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Quality Control of [ 16619-14-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 16619-14-0 ]

SDS Specification

Alternatived Products of [ 16619-14-0 ]

Product Details of [ 16619-14-0 ]

CAS No. :	16619-14-0	MDL No. :	MFCD00098918
Formula :	C₁₅H₁₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PUCZUBFZQVSURB-UHFFFAOYSA-N
M.W :	223.27	Pubchem ID :	10889522
Synonyms :

Calculated chemistry of [ 16619-14-0 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.13
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	71.25
TPSA :	29.1 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.25
Log Po/w (XLOGP3) :	2.92
Log Po/w (WLOGP) :	2.53
Log Po/w (MLOGP) :	2.47
Log Po/w (SILICOS-IT) :	3.25
Consensus Log Po/w :	2.68

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.52
Solubility :	0.0674 mg/ml ; 0.000302 mol/l
Class :	Soluble
Log S (Ali) :	-3.19
Solubility :	0.143 mg/ml ; 0.000642 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.46
Solubility :	0.000772 mg/ml ; 0.00000346 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.31

Safety of [ 16619-14-0 ]

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 [ 16619-14-0 ]

* 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 [ 16619-14-0 ]

[ 16619-14-0 ] Synthesis Path-Downstream 1~84

1
[ 16619-14-0 ]
[ 110-46-3 ]
1-nitroso-2-phenyl-2,3-dihydro-1H-quinolin-4-one [ No CAS ]

Reference： [1]Chemische Berichte,1938,vol. 71,p. 1899

2
[ 78396-00-6 ]
[ 141-52-6 ]
[ 16619-14-0 ]

Reference： [1]Chemische Berichte,1938,vol. 71,p. 1899

3
[ 16619-14-0 ]
[ 108-24-7 ]
[ 60355-89-7 ]
[ 60355-81-9 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761
[2]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761

4
[ 16619-14-0 ]
[ 79-19-6 ]
[ 143237-75-6 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1209 - 1210

5
[ 16619-14-0 ]
[ 93-95-8 ]
[ 113544-25-5 ]
[ 113544-25-5 ]

Reference： [1]Synthetic Communications,1987,vol. 17,p. 1235 - 1246

6
[ 16619-14-0 ]
[ 14802-18-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With iodine; In dimethyl sulfoxide; at 80℃; for 12h;	General procedure: A mixture of 2 (1 mmol) and iodine (1.5 mmol) inDMSO was warmed at 80°C in an oil bath for 12 hours. On completion of the reaction, the reaction mixture was poured onto saturated solution of sodium thiosulfate. The precipitated solid was collected and the desired product was purified by column chromatography using silica gel (60x120 mesh) with increasing percentage of ethyl acetate in hexaneas eluting solvent. The physical data of compounds are provided below.

Reference： [1]Synthetic Communications,1993,vol. 23,p. 277 - 283
[2]Synthetic Communications,1993,vol. 23,p. 277 - 283
[3]Synthetic Communications,1994,vol. 24,p. 2167 - 2172
[4]Letters in drug design and discovery,2013,vol. 10,p. 327 - 334
[5]Archiv der Pharmazie,2013,vol. 346,p. 7 - 16
[6]Synthetic Communications,1994,vol. 24,p. 2167 - 2172

7
[ 16619-14-0 ]
[ 107468-41-7 ]
5-Phenyl-5,6-dihydro-4H-1,2,3,3a,6-pentaaza-benzo[e]azulene [ No CAS ]

Reference： [1]Synthetic Communications,1993,vol. 23,p. 895 - 902
[2]Journal of Chemical Research, Miniprint,1994,p. 367 - 382
[3]Synthetic Communications,1993,vol. 23,p. 895 - 902

8
[ 78396-00-6 ]
[ 16619-14-0 ]
[ 107468-41-7 ]
5-Phenyl-5,6-dihydro-4H-1,2,3,3a,6-pentaaza-benzo[e]azulene [ No CAS ]

Reference： [1]Synthetic Communications,1993,vol. 23,p. 895 - 902

9
[ 78396-00-6 ]
[ 16619-14-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With zirconyl(IV) nitrate hydrate; In ethanol; water; at 50℃; for 3h;Green chemistry;Catalytic behavior;	General procedure: A mixture of the appropriate 2-aminochalcone (1 mmol), EtOH(2 mL), H2O (2 mL), and ZrO(NO3)2·nH2O (46 mg, 20 molpercent) washeated with stirring at 50 °C while the progress of the reactionwas monitored by TLC. The reaction was then quenched withH2O (5 mL), and the mixture was extracted with Et2O (3 × 10mL). The combined organic extracts were washed with brine (5mL) then dried (Na2SO4), filtered, and concentrated underreduced pressure. The crude product was purified by columnchromatography [silica gel, hexane?EtOAc (10:1)]. 2-Phenyl-2,3-dihydroquinolin-4(1H)-one (Table 2, Entry1)5b,6b,11Off-white solid; yield: 218 mg (98percent); mp 153?155 °C. IR (KBr):3060, 3028, 1638, 1572, 1494, 1358, 1324, 1295, 1157, 1095,974, 861 cm?1. 1H NMR (600 MHz, CDCl3): delta = 7.83 (dd, J = 8.5,1.2 Hz, 1 H), 7.42 (d, J = 7.4 Hz, 2 H), 7.40?7.36 (m, 2 H), 7.35?7.33 (m, 2 H), 6.76 (t, J = 7.4 Hz, 1 H), 6.68 (d, J = 8.5 Hz, 1 H),4.70 (dd, J = 13.5, 3.6 Hz, 1 H), 4.65 (s, 1 H, NH), 2.82 (dd, J =16.3, 14.4 Hz, 1 H), 2.70 (dd, J = 15.6, 3.6 Hz, 1 H). 13C NMR (150MHz, CDCl3): delta = 192.9, 152.4, 136.1, 128.6, 128.3, 127.4, 126.5,119.2, 117.2, 116.7, 59.1, 45.7. MS (EI): m/z = 223.10 [M+].

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 13 - 15
[2]Synlett,2018,vol. 29,p. 235 - 237
[3]RSC Advances,2015,vol. 5,p. 85128 - 85138
[4]Canadian Journal of Chemistry,2006,vol. 84,p. 1079 - 1083
[5]Journal of Chemical Research,2009,p. 170 - 173
[6]ChemCatChem,2016,vol. 8,p. 1335 - 1345
[7]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 2111 - 2122
[8]Tetrahedron Letters,2006,vol. 47,p. 2725 - 2729
[9]Angewandte Chemie - International Edition,2013,vol. 52,p. 13280 - 13283
Angew. Chem.,2013,vol. 125,p. 13522 - 13525,4
[10]Asian Journal of Chemistry,2010,vol. 22,p. 6031 - 6034
[11]Synthesis,2004,p. 63 - 68
[12]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 613 - 619
[13]Synlett,1997,vol. 1997,p. 857 - 858
[14]Synthetic Communications,1989,vol. 19,p. 3159 - 3168
[15]Synlett,2006,p. 2791 - 2794
[16]Journal of Medicinal Chemistry,1998,vol. 41,p. 1155 - 1162
[17]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761
[18]Synthetic Communications,1987,vol. 17,p. 1235 - 1246
[19]Tetrahedron Letters,1993,vol. 34,p. 1625 - 1628
[20]Journal of Chemical Research, Miniprint,1994,p. 367 - 382
[21]South African Journal of Chemistry,1994,vol. 47,p. 21 - 25
[22]Canadian Journal of Chemistry,1990,vol. 68,p. 1780 - 1785
[23]Tetrahedron,1997,vol. 53,p. 13397 - 13418
[24]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761

10
[ 131423-38-6 ]
[ 16619-14-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With hydrogenchloride; In water; for 12h;Reflux;	General procedure: A mixture of 1 (1 mmol) and 5percent HCl (10 ml) was refluxed for 12 hours. The reaction mixture was kept at room temperature and then basified with NH4OH. The precipitated solid was filtered sand recrystallized from ethanol. The physical data for the characterstic compound is shown below
4.75 g	With hydrogenchloride; In ethanol; water; for 8h;Reflux;	7.9 g (0.03 mol) of (E)-N-[2-(3-phenylacryloyl)phenyl]acetamide (C1) was dissolved in 80 ml of ethanol. Add 40 ml of 5percent hydrochloric acid and reflux for 8 h. The reaction solution was poured into 200 ml of ice water, and the pH was adjusted to 9 with aqueous ammonia to precipitate a large amount of white solid. Filtering, ethanol recrystallization, 2-phenyl-2,3-dihydro-4(1H)-quinolinone (D1) is obtained as a white solid. The yield is 4.75g, the yield is 71.1percent

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761
[2]Letters in drug design and discovery,2013,vol. 10,p. 327 - 334
[3]Patent: CN108558756,2018,A .Location in patent: Paragraph 0071; 0072; 0073

11
[ 53744-32-4 ]
[ 16619-14-0 ]
[ 14802-18-7 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1994,p. 1741 - 1742

12
[ 16619-14-0 ]
[ 107468-41-7 ]

Reference： [1]Journal of Chemical Research, Miniprint,1995,p. 2319 - 2336

13
4-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-2H-quinoline-1-carboxylic acid benzyl ester [ No CAS ]
[ 16619-14-0 ]

Reference： [1]Synlett,1997,vol. 1997,p. 313 - 315

14
[ 188988-04-7 ]
[ 16619-14-0 ]

Reference： [1]Synlett,1997,vol. 1997,p. 313 - 315

15
[ 188987-98-6 ]
[ 16619-14-0 ]

Reference： [1]Synlett,1997,vol. 1997,p. 313 - 315

16
[ 16619-14-0 ]
[ 149-73-5 ]
[ 22680-62-2 ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 9113 - 9116

17
[ 67-56-1 ]
[ 16619-14-0 ]
[ 22680-62-2 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 7903 - 7906
[2]Journal of Chemical Research - Part S,1999,p. 706 - 707

Yield	Reaction Conditions	Operation in experiment
84%	With C26H18N2O12Ti; In methanol; at 20℃; for 26h;	General procedure: 1.2 mmol of 2-aminoacetophenone and 1.0 mmol of aromatic aldehyde were added to 2 mL of methanol. The reaction was carried out for 26 hours at room temperature, and the results are shown in Table 1.

19
2'-amino-trans-chalcone [ No CAS ]
[ 16619-14-0 ]

Reference： [1]Chemische Berichte,1938,vol. 71,p. 1899

20
2'-nitro-trans-chalcone [ No CAS ]
[ 16619-14-0 ]

Reference： [1]Journal of the Chemical Society,1957,p. 1015

21
[ 551-93-9 ]
[ 100-52-7 ]
[ 16619-14-0 ]
[ 78396-00-6 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 3396 - 3397

22
[ 16619-14-0 ]
[ 119-26-6 ]
N-(2,4-dinitro-phenyl)-N'-(2-phenyl-2,3-dihydro-1H-quinolin-4-ylidene)-hydrazine [ No CAS ]

Reference： [1]Journal of Chemical Research - Part S,2004,p. 218 - 219

23
[ 16619-14-0 ]
[ 64-17-5 ]
[ 22680-63-3 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 7903 - 7906

24
[ 16619-14-0 ]
[ 1144-20-3 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 7903 - 7906

25
[ 16619-14-0 ]
[ 108-24-7 ]
[ 60355-81-9 ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 943 - 950
[2]Journal of the American Chemical Society,2009,vol. 131,p. 18250 - 18251

26
[ 16619-14-0 ]
[ 918165-52-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium tetrahydroborate; In methanol; at 0 - 5℃; for 3h;	To a suspension of 2-phenyl-l,2,3,4-tetrahydiO-4-quinolones (223mg, 1 mmol) in dry methanol (10 mL) is added NaBH4 (4 mmol) and the reaction mixture stirred at 0-50C under nitrogen atmosphere for 3 hr. The reaction mixture is concentrated under reduced pressure and 2M aqueous hydrochloric acid (~2mL) is added to adjust the pH 6. This solution is extracted into diethyl ether (20 mL), washed with water (2 x 15 mL), dried over NaSO4 and concentrated under reduced pressure to give required product. Yield 210 mg (93percent); IR (KBR) 3304, 1453, 1209 cm"1; MS m/z 226.1 (M+H)+.

Reference： [1]Patent: WO2009/87684,2009,A2 .Location in patent: Page/Page column 21
[2]Synlett,2006,p. 2791 - 2794

27
[ 16619-14-0 ]
[ 918165-54-5 ]

Reference： [1]Synlett,2006,p. 2791 - 2794

28
[ 16619-14-0 ]
C₁₆H₁₆ClN [ No CAS ]

Reference： [1]Synlett,2006,p. 2791 - 2794

29
[ 16619-14-0 ]
C₂₅H₁₉NO₃ [ No CAS ]

Reference： [1]Synlett,2006,p. 2791 - 2794

30
[ 551-93-9 ]
[ 16619-14-0 ]

Reference： [1]Synlett,2006,p. 2791 - 2794
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 1155 - 1162
[3]South African Journal of Chemistry,1994,vol. 47,p. 21 - 25
[4]Journal of Chemical Research, Miniprint,1994,p. 367 - 382
[5]Synthetic Communications,1987,vol. 17,p. 1235 - 1246
[6]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761
[7]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761
[8]Archiv der Pharmazie,2013,vol. 346,p. 7 - 16
[9]Letters in drug design and discovery,2013,vol. 10,p. 327 - 334
[10]Organic Letters,2015,vol. 17,p. 3202 - 3205
[11]Patent: CN108558756,2018,A

31
[ 100-52-7 ]
Fmoc-L-tert-leucine on Wang resin [ No CAS ]
[ 16619-14-0 ]

Reference： [1]Synlett,2006,p. 2791 - 2794

32
[ 16619-14-0 ]
trans-methyl N-acetyl-2-phenyl-2,3-dihydroindol-3-carboxylate [ No CAS ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 943 - 950

33
[ 16619-14-0 ]
[ 22680-62-2 ]

Reference： [1]Synthetic Communications,2006,vol. 36,p. 943 - 950

34
[ 16619-14-0 ]
2-(2,4-dinitrophenyl)-5-formyl-4,5-dihydro-4-phenyl-2H-pyrazolo[4,3-c]quinoline [ No CAS ]

Reference： [1]Journal of Chemical Research - Part S,2004,p. 218 - 219

35
[ 4187-87-5 ]
[ 16619-14-0 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 13397 - 13418
[2]Tetrahedron Letters,1993,vol. 34,p. 1625 - 1628

36
[ 143321-89-5 ]
[ 16619-14-0 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 13397 - 13418
[2]Tetrahedron Letters,1993,vol. 34,p. 1625 - 1628

37
[ 155694-57-8 ]
[ 16619-14-0 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 13397 - 13418
[2]Tetrahedron Letters,1993,vol. 34,p. 1625 - 1628

38
[ 148564-90-3 ]
[ 16619-14-0 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 13397 - 13418
[2]Tetrahedron Letters,1993,vol. 34,p. 1625 - 1628

39
[ 100-52-7 ]
C-phenyl-C-<2-methoxy-naphthyl-⁽¹⁾>-methylamine [ No CAS ]
[ 16619-14-0 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1155 - 1162
[2]South African Journal of Chemistry,1994,vol. 47,p. 21 - 25

40
[ 172538-83-9 ]
[ 16619-14-0 ]

Reference： [1]Synlett,1997,vol. 1997,p. 313 - 315
[2]Synlett,1997,vol. 1997,p. 313 - 315

41
Trifluoro-methanesulfonate1-benzyloxycarbonyl-4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-quinolinium; [ No CAS ]
[ 16619-14-0 ]

Reference： [1]Synlett,1997,vol. 1997,p. 313 - 315

42
Trifluoro-methanesulfonate1-benzyloxycarbonyl-4-triisopropylsilanyloxy-quinolinium; [ No CAS ]
[ 16619-14-0 ]

Reference： [1]Synlett,1997,vol. 1997,p. 313 - 315

43
[ 100-52-7 ]
sodium cyanate [ No CAS ]
[ 16619-14-0 ]

Reference： [1]Journal of Chemical Research, Miniprint,1994,p. 367 - 382

44
[ 16619-14-0 ]
[ 113567-28-5 ]

Reference： [1]Synthetic Communications,1987,vol. 17,p. 1235 - 1246

45
[ 16619-14-0 ]
[ 113567-29-6 ]

Reference： [1]Synthetic Communications,1987,vol. 17,p. 1235 - 1246

46
[ 100-52-7 ]
oxygen [ No CAS ]
[ 16619-14-0 ]

Reference： [1]Synthetic Communications,1987,vol. 17,p. 1235 - 1246

47
[ 16619-14-0 ]
[ 143237-76-7 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 1209 - 1210

48
[ 124856-96-8 ]
[ 16619-14-0 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761

49
[ 100-52-7 ]
[ 16619-14-0 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761
[2]Journal of Organic Chemistry,1990,vol. 55,p. 1757 - 1761
[3]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 613 - 619
[4]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 613 - 619
[5]Organic Letters,2015,vol. 17,p. 3202 - 3205

50
[ 78396-00-6 ]
[ 16619-14-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 1-butyl-3-methylimidazolium Tetrafluoroborate; at 150℃; for 2.5h;	In a typical reaction 2'-aminochalcone21 (1a) (100 mg, 0.448 mmol) and [bmim]BF4 (1 g) were placed in a 25 mL round-bottomed flask fitted with a condenser and a magnetic stir bar. A homogeneous solution was obtained on heating at 150 °C which was stirred at this temperature for 2.5 h. The crude product was isolated by repeated extraction with diethyl ether (7 .x. 10 mL) followed by evaporation. Filtration of the residue through a silica plug using CH2Cl2 as the eluent gave 2-phenyl-2,3-dihydroquinolin-4(1H)-one (2a).

Reference： [1]Synthetic Communications,2010,vol. 40,p. 476 - 481
[2]Synthetic Communications,2013,vol. 43,p. 1023 - 1029
[3]Comptes Rendus Chimie,2011,vol. 14,p. 1059 - 1064
[4]Synthetic Communications,2010,vol. 40,p. 1391 - 1398
[5]Tetrahedron Letters,2008,vol. 49,p. 6974 - 6976
[6]Organic Letters,2015,vol. 17,p. 3202 - 3205
[7]Journal of Heterocyclic Chemistry,2009,vol. 46,p. 791 - 795
[8]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 1356 - 1360
[9]Tetrahedron Letters,2012,vol. 53,p. 4059 - 4061

51
[ 16619-14-0 ]
[ 1133158-36-7 ]

Reference： [1]Synthetic Communications,2009,vol. 39,p. 596 - 603

52
[ 872-85-5 ]
[ 16619-14-0 ]
[ 1171953-00-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium hydroxide; In ethanol; water; at 20℃; for 24h;	An aqueous sodium hydroxide solution (6N, 2 mL) is added to a solution of 2- phenyl - 2, 3 - dihydroquinolin-4(lH)-one (223 mg, lmmol) in ethanol (5mL). Pyridine -4- carboxaldehyde (126 mg, 1.2 mmol) is then added to the reaction mixture, which is stirred at room temperature for 24 hours. Subsequently, it is evaporated under reduced pressure. The residue is dissolved into chloroform and the organic layer washed with water, dried over Na2SO4 and evaporated to dryness. Crude product further purified by column chromatography on silica gel using ethyl acetate: acetone (97:03 v/v) as eluent. Yield 130 mg (42percent); mp 222-224°C; IR (KBR) 3435, 1627 cm"1; 13C NMR (DMSO-d6) delta 30.84 (CH2), 116.04 (C-8), 118.40 (C-6), 123.16 (C-3), 123.39 (C-2" and C-6"), 123.76 (C-4'), 125.09 (C-4a), 128.61 (C-2' and C-6'), 128.66 (C-3' and C-5'), 129.67 (C-5), 131.73 (C-7), 134.58 (C-I'), 139.65 (C-2), 149.16 (C-3" and C-5"), 149.64 (C-I"), 150.49 (C-8a), 176.21 (C=O).

Reference： [1]Patent: WO2009/87684,2009,A2 .Location in patent: Page/Page column 29

53
[ 16619-14-0 ]
[ 3066-75-9 ]
C₁₈H₁₇NO [ No CAS ]
[ 1203590-92-4 ]
[ 113567-28-5 ]
[ 113567-29-6 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 18250 - 18251

54
[ 551-93-9 ]
[ 100-52-7 ]
[ 16619-14-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With C22H48N4O12S4(4+)*4HO4S(1-); In ethanol; water; at 20℃; for 2.1h;Irradiation; Reflux;	1 mmol of benzaldehyde,1 mmol of o-aminoacetophenone and 0.10 mmol of high acidity ionic liquid were separately added to a 50 ml single-necked flask with a condenser tube containing 8 ml of a 94% aqueous ethanol solution and stirred at room temperature.Heating and refluxing, ultrasonic irradiation under the reaction 2.1h, TLC (thin plate chromatography) detection, the raw material disappeared, the end of the reaction to room temperature precipitation of a large number of solid, Into the ice water bath to continue to cool out the solid, the amount of solid is no longer increased when the crushing of the solid, standing, suction, Washed with ethanol (3 ml x 3) and dried in vacuo at 75 C to give 2-phenyl-2,3-dihydro-4 (1H) -quinolinone, The purity was 99.1% and the yield was 92%. The filtrate is directly added with benzaldehyde and o-aminoacetophenone reuse.
88%	With silver trifluoromethanesulfonate; In methanol; for 12h;Reflux; Inert atmosphere;	General procedure: AgOTf (26 mg, 10 mol%) was added to a solution of an o-aminoacetophenone (1.0 mmol) and an aryl aldehyde (1.2 mmol) in MeOH (5mL) at r.t. The reaction mixture was stirred under reflux for 12-24 h. After the reaction was complete, as indicated by TLC, the excess solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexanes-EtOAc, 20:1) to yield the desired product.
	With L-proline; In methanol; for 48h;	General procedure: To a solution of L-Proline (0.44 mmol) in methanol (5 mL) was added 2-aminoacetophenone (1.4 mmol) and aldehyde (1.4 mmol) and the mixture was stirred for 48 h. The mixture was treated with 5 mL of saturated ammonium chloride solution and extracted with dichloromethane (3 x 10 mL). The combined organic layer was dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by column chromatography.

Reference： [1]Patent: CN107162970,2017,A .Location in patent: Paragraph 0041; 0042; 0043
[2]Synthesis,2015,vol. 47,p. 3881 - 3890
[3]Applied Organometallic Chemistry,2019,vol. 33
[4]Synthetic Communications,2010,vol. 40,p. 1391 - 1398
[5]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 645 - 648
[6]Tetrahedron Letters,2012,vol. 53,p. 4059 - 4061
[7]Tetrahedron Letters,2016,vol. 57,p. 5442 - 5445

55
C₁₅H₁₂NOPolSe [ No CAS ]
[ 16619-14-0 ]

Reference： [1]Synlett,2011,p. 707 - 711

56
[ 577-59-3 ]
[ 16619-14-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 613 - 619
[2]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 613 - 619
[3]MedChemComm,2017,vol. 8,p. 1618 - 1630
[4]Patent: CN108558756,2018,A

57
[ 53744-32-4 ]
[ 16619-14-0 ]

Reference： [1]ChemCatChem,2016,vol. 8,p. 1335 - 1345
[2]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 613 - 619
[3]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 613 - 619
[4]ChemCatChem,2016,vol. 8,p. 1335 - 1345

58
[ 16619-14-0 ]
[ 1332337-51-5 ]