16619-14-0|2-Phenyl-2,3-dihydroquinolin-4(1H)-one| Ambeed

CAS No. :	16619-14-0
Formula :	C₁₅H₁₃NO
M.W :	223.27
SMILES Code :	C1(=CC=CC=C1)C3CC(C2=CC=CC=C2N3)=O
MDL No. :	MFCD00098918
InChI Key :	PUCZUBFZQVSURB-UHFFFAOYSA-N
Pubchem ID :	10889522

Safety of [ 16619-14-0 ]

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

Computational Chemistry of [ 16619-14-0 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.1 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.25
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.92
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.53
Log P_o/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.	2.47
Log P_o/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	3.25
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.68

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.52
Solubility	0.0674 mg/ml ; 0.000302 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.19
Solubility	0.143 mg/ml ; 0.000642 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < 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	-5.46
Solubility	0.000772 mg/ml ; 0.00000346 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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	Yes
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	Yes
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.	-5.59 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	0.0
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)	2.31

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 1~54

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

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

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

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

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

References: [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 ]

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

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

References: [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.

References: [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 ]

References: [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 ]

References: [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+].

References: [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

References: [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 ]

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

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

References: [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 ]

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

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

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

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

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

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

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

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

References: [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 ]

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

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

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

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

References: [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 ]

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

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

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

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

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

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

References: [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)+.

References: [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 ]

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

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

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

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

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

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

References: [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 ]

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

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

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

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

References: [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 ]

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

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

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

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

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

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

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

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

References: [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 ]

References: [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 ]

References: [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 ]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

References: [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).

References: [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 ]

References: [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).

References: [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 ]

References: [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.

References: [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.

Historical Records

Technical Information

• Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 16619-14-0 ]

Aryls

A248683 [155370-03-9]

2-(4-Fluorophenyl)-2,3-dihydro-4(1H)-quinolinone

Similarity: 0.86

A127363 [1859-75-2]

1-(2-(Methylamino)phenyl)ethanone

Similarity: 0.82

A266487 [96293-17-3]

(S)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

Similarity: 0.80

A341976 [105024-93-9]

(R)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

Similarity: 0.80

Ketones

A193685 [1127-74-8]

1,2,3,4-Tetrahydrobenzo[b]azepin-5-one

Similarity: 0.89

A338333 [21737-58-6]

5H-Dibenzo[b,f]azepin-10(11H)-one

Similarity: 0.89

A248683 [155370-03-9]

2-(4-Fluorophenyl)-2,3-dihydro-4(1H)-quinolinone

Similarity: 0.86

A213639 [1143-50-6]

5H-Dibenzo[b,e]azepine-6,11-dione

Similarity: 0.83

A127363 [1859-75-2]

1-(2-(Methylamino)phenyl)ethanone

Similarity: 0.82

Related Parent Nucleus of
[ 16619-14-0 ]

Tetrahydroquinolines

A248683 [155370-03-9]

2-(4-Fluorophenyl)-2,3-dihydro-4(1H)-quinolinone

Similarity: 0.86

A115583 [4295-36-7]

2,3-Dihydroquinolin-4(1H)-one

Similarity: 0.80

A170468 [113961-88-9]

1-(1,2,3,4-Tetrahydroquinolin-6-yl)ethanone

Similarity: 0.80

A112726 [71412-22-1]

2,3-Dihydroquinolin-4(1H)-one hydrochloride

Similarity: 0.79

A132202 [52851-41-9]

Quinoline-2,4(1H,3H)-dione

Similarity: 0.76

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