Home Cart Sign in  
Chemical Structure| 53400-41-2 Chemical Structure| 53400-41-2

Structure of 53400-41-2

Chemical Structure| 53400-41-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

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

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 53400-41-2 ]

CAS No. :53400-41-2
Formula : C9H9NO
M.W : 147.17
SMILES Code : O=C1CCCC2=C1C=CC=N2
MDL No. :MFCD03839916
InChI Key :YHHBKPWMEXGLKE-UHFFFAOYSA-N
Pubchem ID :3016811

Safety of [ 53400-41-2 ]

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

Computational Chemistry of [ 53400-41-2 ] Show Less

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 ?

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

29.96 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.56
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

0.99
Log Po/w (WLOGP)?

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

1.6
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.

0.78
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

2.53
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.49

Water Solubility

Log S (ESOL):?

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

-1.78
Solubility 2.44 mg/ml ; 0.0166 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.

-1.21
Solubility 9.12 mg/ml ; 0.062 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

-3.0
Solubility 0.147 mg/ml ; 0.000998 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.

-6.49 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)

1.81

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.

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

[ 53400-41-2 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 53400-41-2 ]
  • [ 70-23-5 ]
  • 1-(2-Ethoxycarbonyl-2-oxo-ethyl)-5-oxo-5,6,7,8-tetrahydro-quinolinium; bromide [ No CAS ]
  • 3
  • [ 53400-41-2 ]
  • [ 2537-48-6 ]
  • [ 85774-75-0 ]
  • 4
  • [ 53400-41-2 ]
  • [ 2537-48-6 ]
  • [ 85774-77-2 ]
  • [ 85774-75-0 ]
  • 5
  • [ 53400-41-2 ]
  • [ 917-54-4 ]
  • [ 97112-08-8 ]
  • 6
  • [ 53400-41-2 ]
  • [ 151-50-8 ]
  • [ 66892-50-0 ]
  • 7
  • [ 53400-41-2 ]
  • [ 194151-99-0 ]
YieldReaction ConditionsOperation 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.
  • 8
  • [ 53400-41-2 ]
  • [ 1006-51-5 ]
  • 9
  • [ 53400-41-2 ]
  • [ 90725-51-2 ]
  • 11
  • [ 53400-41-2 ]
  • [ 591-51-5 ]
  • [ 60975-88-4 ]
  • 12
  • [ 53400-41-2 ]
  • [ 70-11-1 ]
  • [ 129574-56-7 ]
  • 13
  • [ 52035-11-7 ]
  • [ 107-02-8 ]
  • [ 53400-41-2 ]
  • 14
  • [ 53400-41-2 ]
  • [ 68-12-2 ]
  • 5-Bromo-7,8-dihydroquinoline-6-carbaldehyde [ No CAS ]
  • 16
  • [ 53400-41-2 ]
  • [ 26961-27-3 ]
  • 2-[7,8-Dihydro-6H-quinolin-(5E)-ylideneamino]-4,5-dimethoxy-benzonitrile [ No CAS ]
  • 17
  • [ 53400-41-2 ]
  • [ 26759-46-6 ]
  • 2-[7,8-Dihydro-6H-quinolin-(5E)-ylideneamino]-4,5-dimethoxy-benzoic acid methyl ester [ No CAS ]
  • 19
  • [ 53400-41-2 ]
  • [ 87-25-2 ]
  • 2-[7,8-Dihydro-6H-quinolin-(5E)-ylideneamino]-benzoic acid ethyl ester [ No CAS ]
  • 20
  • [ 53400-41-2 ]
  • [ 1885-29-6 ]
  • 2-[7,8-Dihydro-6H-quinolin-(5E)-ylideneamino]-benzonitrile [ No CAS ]
  • 21
  • [ 122-31-6 ]
  • [ 504-02-9 ]
  • [ 53400-41-2 ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; In xylene; at 160℃; for 18h; In a nitrogen atmosphere, 24 mL of malonaldehyde tetraethyl acetal and 7.71 g of ammonium acetate were added in that order to xylene (80 mL) solution of 11.2 g of 1,3-cyclohexadione, and a reflux condenser tube fitted with a Dean-Stark water separator was attached to the reactor, and this was stirred at 160C for 18 hours. The reaction liquid was cooled to room temperature, the solvent was evaporated off under reduced pressure, the residue was extracted with chloroform, and the chloroform layer was washed with saturated saline water and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (chloroform/methanol = 97/3) to obtain 2.21 g of the entitled compound.
  • 22
  • [ 122-31-6 ]
  • [ 5220-49-5 ]
  • [ 53400-41-2 ]
YieldReaction ConditionsOperation in experiment
7% toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 16h;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 lambda/,lambda/-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 7% yield as a colorless oil.
toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 140℃; for 18h; To a solution of 10.12 g (0.14 mmol) 3-aminocyclohex-2-en-l-one and 22 mL 1,1,3,3- tetraethoxypropane in 40 mL dry DMF under nitrogen atmosphere was added 0.5 g (cat.) p- toluenesulfonic acid. The reaction mixture was heated at 140 0C for 18 hr. The volatiles were removed under vacuum and the residue distilled under vacuum to give an oil. This material was further purified by column chromatography on silica gel eluting with hexanes/EtOAc (3/1) then EtOAc (100%) afford 1.75 g of the title compound. LC-MS: (MH)+: 148.2.
YieldReaction ConditionsOperation in experiment
EXAMPLE 32 4,5-Dihydro-1H(and 2H)pyrazolo[3,4-fquinoline Following the procedure of Ramalingam, K., et al. (Journal of Medicinal Chemistry, Vol. 20, pp. 664-669 (1977)), from 33.5 g (0.228 mol) of 7,8-dihydro-5(6H)-quinolinone (Example 1) is obtained 25.0 g (64%) of the title compound after recrystallization from acetonitrile; mp 206-211 C.
  • 27
  • [ 5220-49-5 ]
  • [ 927-63-9 ]
  • [ 53400-41-2 ]
  • [ 56798-21-1 ]
  • 28
  • [ 624-67-9 ]
  • 1-aminocyclohexan-3-one [ No CAS ]
  • [ 53400-41-2 ]
  • 29
  • [ 53400-41-2 ]
  • [ 1030268-21-3 ]
  • [ 273930-08-8 ]
  • 30
  • [ 53400-41-2 ]
  • [ 616-38-6 ]
  • [ 375386-65-5 ]
  • 31
  • 3-(3-hydroxy-propylamino)-cyclohex-2-enone [ No CAS ]
  • [ 53400-41-2 ]
  • 32
  • [ 3389-21-7 ]
  • [ 53400-41-2 ]
  • 1-[2-(1<i>H</i>-indol-3-yl)-ethyl]-5-oxo-5,6,7,8-tetrahydro-quinolinium; bromide [ No CAS ]
  • 33
  • [ 53400-41-2 ]
  • [ 105-58-8 ]
  • [ 864499-13-8 ]
  • 34
  • [ 53400-41-2 ]
  • [ 19501-58-7 ]
  • [ 880553-71-9 ]
  • 35
  • [ 53400-41-2 ]
  • [ 39232-91-2 ]
  • [ 880553-77-5 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 53400-41-2 ]

Ketones

Chemical Structure| 56826-69-8

A149328 [56826-69-8]

6,7-Dihydro-5H-quinoline-8-one

Similarity: 0.92

Chemical Structure| 10470-83-4

A250977 [10470-83-4]

5,8-Quinolinequinone

Similarity: 0.85

Chemical Structure| 127724-75-8

A110155 [127724-75-8]

3-Chloro-7,8-dihydroquinolin-5(6H)-one

Similarity: 0.83

Chemical Structure| 56234-20-9

A117921 [56234-20-9]

1-(Quinolin-8-yl)ethanone

Similarity: 0.80

Chemical Structure| 100866-13-5

A370138 [100866-13-5]

2-(Pyridin-4-yl)-1-(p-tolyl)ethanone

Similarity: 0.76

Related Parent Nucleus of
[ 53400-41-2 ]

Other Aromatic Heterocycles

Chemical Structure| 56826-69-8

A149328 [56826-69-8]

6,7-Dihydro-5H-quinoline-8-one

Similarity: 0.92

Chemical Structure| 127724-75-8

A110155 [127724-75-8]

3-Chloro-7,8-dihydroquinolin-5(6H)-one

Similarity: 0.83

Chemical Structure| 10500-57-9

A371016 [10500-57-9]

5,6,7,8-Tetrahydroquinoline

Similarity: 0.77

Chemical Structure| 1256822-12-4

A156527 [1256822-12-4]

5,6,7,8-Tetrahydroquinoline-6-carboxylic acid

Similarity: 0.73

Chemical Structure| 67058-71-3

A100277 [67058-71-3]

1-(1H-Pyrrolo[2,3-c]pyridin-3-yl)ethanone

Similarity: 0.73