[ CAS No. 53400-41-2 ] {[proInfo.proName]}

Name: 53400-41-2|7,8-Dihydroquinolin-5(6H)-one|97%
Brand: Ambeed
SKU: A156644
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Quality Control of [ 53400-41-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 53400-41-2 ]

Product Details of [ 53400-41-2 ]

CAS No. :	53400-41-2	MDL No. :	MFCD03839916
Formula :	C₉H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YHHBKPWMEXGLKE-UHFFFAOYSA-N
M.W :	147.17	Pubchem ID :	3016811
Synonyms :

Calculated chemistry of [ 53400-41-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.09
TPSA :	29.96 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.56
Log Po/w (XLOGP3) :	0.99
Log Po/w (WLOGP) :	1.6
Log Po/w (MLOGP) :	0.78
Log Po/w (SILICOS-IT) :	2.53
Consensus Log Po/w :	1.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.78
Solubility :	2.44 mg/ml ; 0.0166 mol/l
Class :	Very soluble
Log S (Ali) :	-1.21
Solubility :	9.12 mg/ml ; 0.062 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.0
Solubility :	0.147 mg/ml ; 0.000998 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.81

Safety of [ 53400-41-2 ]

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

Application In Synthesis of [ 53400-41-2 ]

* 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 [ 53400-41-2 ]
Downstream synthetic route of [ 53400-41-2 ]

[ 53400-41-2 ] Synthesis Path-Upstream 1~12

1
[ 10500-57-9 ]
[ 53400-41-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tert.-butylhydroperoxide; manganese(II) triflate In water at 20℃; for 24 h;	0.883 mg of Mn (OTf) 2 (0.5 molpercent), 67 mg of 5,6,7,8-tetrahydroquinoline, 0.35 g of a 65percent aqueous TBHP solution, 2.5 ml of water, was added in turn to a 25 mL round bottom flask, in the air at room temperature for 24 hours, the reaction solution was extracted with 3 x 5 mL of ethyl acetate, the ethyl acetate layer was collected, dried over anhydrous sodium sulfate, filtered, evaporation of ethyl acetate, petroleum ether and ethyl acetate (5: 1, v / v) as the eluent, the product 5,6,7,8-tetrahydroquinolin-5-one (56.6 mg) was isolated by silica gel column chromatography, light yellow liquid, yield 77percent.

Reference： [1] Patent: CN105669548, 2016, A, . Location in patent: Paragraph 0029; 0030

2
[ 122-31-6 ]
[ 5220-49-5 ]
[ 53400-41-2 ]

Yield	Reaction Conditions	Operation in experiment
7%	for 16 h; Heating / reflux	A mixture of 3-aminocyclohex-2-enone (100 mmol), 1 ,1 , 3,3- tetraethoxypropane (1 10 mmol), and 4-methylbenzenesulfonic acid (2.91 mmol) is diluted with λ/,λ/-dimethylformamide (40 ml_) and the reaction mixture is heated at reflux for 16 h. The reaction mixture is allowed to cool to rt, neutralized with sodium bicarbonate, diluted with water (400 ml_), and is extracted with ethyl acetate (3 x 100 ml_). The combined organic layers are dried (sodium sulfate) and concentrated. The residue is purified by chromatography (10/1 petroleum ether/ethyl acetate) to provide 5,6,7,8-tetrahydroquinolin-5-one in 7percent yield as a colorless oil.

Reference： [1] Synthetic Communications, 1998, vol. 28, # 7, p. 1197 - 1200
[2] Tetrahedron, 2003, vol. 59, # 43, p. 8589 - 8595
[3] Patent: WO2009/55437, 2009, A2, . Location in patent: Page/Page column 60; 61
[4] Patent: WO2006/60344, 2006, A2, . Location in patent: Page/Page column 22

3
[ 122-31-6 ]
[ 504-02-9 ]
[ 53400-41-2 ]

Reference： [1] Synthetic Communications, 1998, vol. 28, # 7, p. 1197 - 1200
[2] Patent: EP1726590, 2006, A1, . Location in patent: Page/Page column 35

4
[ 504-02-9 ]
[ 107-02-8 ]
[ 53400-41-2 ]

Reference： [1] Patent: EP2937348, 2015, A1, . Location in patent: Paragraph 0016; 0017; 0018

5
[ 624-67-9 ]
[ 53400-41-2 ]

Reference： [1] Journal of the American Chemical Society, 2000, vol. 122, # 3, p. 437 - 443

6
[ 87549-96-0 ]
[ 21917-88-4 ]
[ 53400-41-2 ]

Reference： [1] Organic Letters, 2018,

7
[ 624-67-9 ]
[ 5220-49-5 ]
[ 53400-41-2 ]

Reference： [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2736 - 2746
[2] Journal of Organic Chemistry, 1985, vol. 50, # 20, p. 3938 - 3940
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 213 - 220
[4] Journal of Medicinal Chemistry, 1998, vol. 41, # 12, p. 2146 - 2163

8
[ 52035-11-7 ]
[ 107-02-8 ]
[ 53400-41-2 ]

Reference： [1] Tetrahedron, 1995, vol. 51, # 4, p. 1265 - 1276

9
[ 5220-49-5 ]
[ 53400-41-2 ]

Reference： [1] Patent: US4762843, 1988, A,

10
[ 504-02-9 ]
[ 156-87-6 ]
[ 53400-41-2 ]

Reference： [1] Synthetic Communications, 2010, vol. 40, # 11, p. 1708 - 1716

11
[ 5220-49-5 ]
[ 927-63-9 ]
[ 53400-41-2 ]
[ 56798-21-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2000, vol. 37, # 1, p. 41 - 46

12
[ 504-02-9 ]
[ 53400-41-2 ]

Reference： [1] Synthetic Communications, 1998, vol. 28, # 7, p. 1197 - 1200

[ 53400-41-2 ] Synthesis Path-Downstream 1~88

1
[ 3638-64-0 ]
[ 53400-41-2 ]
[ 84133-37-9 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 6603 - 6609
[2]Journal of Organic Chemistry,1983,vol. 48,p. 492 - 494

2
[ 53400-41-2 ]
[ 70-23-5 ]
1-(2-Ethoxycarbonyl-2-oxo-ethyl)-5-oxo-5,6,7,8-tetrahydro-quinolinium; bromide [ No CAS ]

Reference： [1]Heterocycles,1990,vol. 31,p. 563 - 568

3
[ 53400-41-2 ]
[ 2537-48-6 ]
[ 85774-75-0 ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 297 - 302

4
[ 53400-41-2 ]
[ 2537-48-6 ]
[ 85774-77-2 ]
[ 85774-75-0 ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 297 - 302

5
[ 53400-41-2 ]
[ 917-54-4 ]
[ 97112-08-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 213 - 220

6
[ 53400-41-2 ]
[ 151-50-8 ]
[ 66892-50-0 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 230 - 243

7
[ 53400-41-2 ]
[ 194151-99-0 ]

Yield	Reaction Conditions	Operation in experiment
90.9%	With sodium tetrahydroborate; In ethanol; at 25℃; for 16h;	7,8-dihydro-quinoline -5 (6H) - one (2.2g, 14.9mmol) was dissolved in ethanol (20 mL) was added NaBH4 (1.2g, 31.7mmol), 25 reaction was stirred for 16 hours. The reaction mixture was washed with water (30mL) was quenched by adding ethyl acetate (20mL × 3) organic phases spin dry to give the title compound as a white solid (2g, 90.9% yield).
	With sodium tetrahydroborate; In methanol; ethyl acetate;	Step 1. A stirred solution of (5,6,7,8)-tetrahydroquinoline-5-one (500 mg, 3.4 mmol) in MeOH (17 mL) was cooled to 0 C. under Argon and treated with NaBH4 (128.7 mg, 3.4 mmol). The reaction was stirred over 16 h and allowed to warm to ambient temperature. The solvent was removed under reduced pressure and the crude oil was chromatographed on a silica gel column packed in 95:5 EtOAc:hexanes and eluted with same. The appropriate fractions were combined and the solvent was removed under reduced pressure to give the 5-hydroxy-(5,6,7,8)-tetrahydroquinoline.

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 3938 - 3940
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 2146 - 2163
[3]Archiv der Pharmazie,1999,vol. 332,p. 358 - 362
[4]Patent: CN105884752,2016,A .Location in patent: Paragraph 0285; 0286; 0287
[5]Patent: US5726172,1998,A

8
[ 53400-41-2 ]
[ 1006-51-5 ]

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 3938 - 3940

9
[ 53400-41-2 ]
[ 90725-51-2 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2736 - 2746

10
[ 624-67-9 ]
[ 5220-49-5 ]
[ 53400-41-2 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2736 - 2746
[2]Journal of Organic Chemistry,1985,vol. 50,p. 3938 - 3940
[3]Journal of the Chemical Society. Perkin transactions I,1985,p. 213 - 220
[4]Journal of Medicinal Chemistry,1998,vol. 41,p. 2146 - 2163

11
[ 53400-41-2 ]
[ 19501-58-7 ]
[ 880553-71-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3233 - 3237

12
[ 53400-41-2 ]
[ 39232-91-2 ]
[ 880553-77-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3233 - 3237

13
[ 53400-41-2 ]
ethyl 5-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-7-carboxylate [ No CAS ]

Reference： [1]Synthesis,2005,p. 1593 - 1600

14
[ 53400-41-2 ]
6-hydroxymethyl-5-oxo-5,6,7,8-tetrahydro-quinoline-6-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Synthesis,2005,p. 1593 - 1600

15
[ 53400-41-2 ]
[ 864499-19-4 ]

Reference： [1]Synthesis,2005,p. 1593 - 1600

16
[ 53400-41-2 ]
[ 84133-39-1 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 6603 - 6609
[2]Journal of Organic Chemistry,1983,vol. 48,p. 492 - 494

17
[ 53400-41-2 ]
[ 344335-31-5 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 6603 - 6609

18
[ 53400-41-2 ]
5-hydroxy-5,6,7,8-tetrahydroquinoline-6-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 8589 - 8595

19
[ 53400-41-2 ]
5-hydroxy-5,6,7,8-tetrahydroquinoline-6-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 8589 - 8595

20
[ 53400-41-2 ]
[ 635291-61-1 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 8589 - 8595
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 7440 - 7443
Angew. Chem.,2017,vol. 129,p. 7548 - 7551,4

21
[ 53400-41-2 ]
[ 635291-63-3 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 8589 - 8595

22
[ 53400-41-2 ]
[ 635291-62-2 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 8589 - 8595

23
[ 504-02-9 ]
aqueous hydrocyanic acid [ No CAS ]
[ 53400-41-2 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 8589 - 8595
[2]Tetrahedron Letters,2002,vol. 43,p. 7929 - 7932

24
[ 53400-41-2 ]
[ 375386-68-8 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 6593 - 6594

25
[ 53400-41-2 ]
(4aRS,12bRS,14aRS)-3,4,4a,6,7,12,12b,13,14,14a-decahydroindolo[2',3':3,4]pyrido[1,2-a]pyrido[1,2-a]quinolin-2-ylmethanol [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 6593 - 6594

26
[ 53400-41-2 ]
(4aS,11bS,13aS)-3,4,4a,5,6,11,11b,12,13,13a-Decahydro-4b,11-diaza-indeno[2,1-a]phenanthrene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 6593 - 6594

27
[ 53400-41-2 ]
[ 375386-69-9 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 6593 - 6594

28
[ 53400-41-2 ]
(4aS,11bS,13aR)-1-Hydroxy-1,2,3,4,4a,5,6,11,11b,12,13,13a-dodecahydro-4b,11-diaza-indeno[2,1-a]phenanthrene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 6593 - 6594

29
[ 53400-41-2 ]
(4aS,11bS,13aR)-1-Methanesulfonyloxy-1,2,3,4,4a,5,6,11,11b,12,13,13a-dodecahydro-4b,11-diaza-indeno[2,1-a]phenanthrene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 6593 - 6594

30
[ 53400-41-2 ]
1-[2-(1H-indol-3-yl)-ethyl]-6-methoxycarbonyl-5-oxo-5,6,7,8-tetrahydro-quinolinium; bromide [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 6593 - 6594

31
[ 53400-41-2 ]
5-imidazol-1-ylmethyl-5,6,7,8-tetrahydro-quinoline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1841 - 1851

32
[ 53400-41-2 ]
5-[(imidazol-1-yl)methyl]-5,6,7,8-tetrahydroquinolin-5-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1841 - 1851

33
[ 53400-41-2 ]
5-(1-imidazolylcarbonyloxy)-5,6,7,8-tetrahydroquinoline [ No CAS ]

Reference： [1]Archiv der Pharmazie,1999,vol. 332,p. 358 - 362

34
[ 53400-41-2 ]
[ 219821-48-4 ]