98453-60-2|6-Bromo-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one| Ambeed

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Quality Control of [ 98453-60-2 ] Purity: 97% SDS Specification

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Product Details of [ 98453-60-2 ]

CAS No. :	98453-60-2
Formula :	C₁₂H₁₃BrO
M.W :	253.14
SMILES Code :	O=C1C2C=CC(=CC=2C(C)(C)CC1)Br
MDL No. :	MFCD22041940
InChI Key :	HWRLTYBJEKHTJG-UHFFFAOYSA-N
Pubchem ID :	11831935

Safety of [ 98453-60-2 ]

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

Computational Chemistry of [ 98453-60-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.42
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	61.49
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.58
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	3.59
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.7
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.	3.25
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	4.17
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.46

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.99
Solubility	0.026 mg/ml ; 0.000103 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.	-3.64
Solubility	0.0587 mg/ml ; 0.000232 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	-5.01
Solubility	0.00245 mg/ml ; 0.00000966 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	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	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.	-5.3 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)	2.04

Application In Synthesis of [ 98453-60-2 ]

* 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 [ 98453-60-2 ]

[ 98453-60-2 ] Synthesis Path-Downstream 1~26

1
[ 98453-58-8 ]
[ 98453-60-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With chromium(VI) oxide; tert.-butylhydroperoxide; In dichloromethane; at 20℃; for 8h;	6-Bromo-4, 4-dimethyl-3, 4-dihydro-2H-naphthalen-1-one (Compound 3) To a solution of 7-bromo-1, 1-dimethyl-1, 2,3, 4-tetrahydro-naphthalene (Compound 2, 1. 1 g, 4.62 mmol) in 10 mL of dichloromethane was added chromium (VI) oxide (72 mg, 0.46 mmol) and 5 mL of ter-butyl hydroperoxide solution (TBHP). After stirring at room temperature for 8 h, the mixture was diluted with water (20 mL), extracted with diethyl ether (3x 10 mL), washed with brine (1 x 10 mL), dried (MgS04) and concentrated at reduced pressure. Purification by flash chromatography (90: 10 hexane/ethyl acetate) yielded the title compound (920 mg, 79 percent yield) as a white solid: 1H NMR (CDC13, 300 MHz) 8 7.87 (d, J = 8. 1 Hz, 1H), 7.54 (d, J = 2.1 Hz, 1H), 7.42 (dd, J = 2.1, 8.1 Hz, 1H), 2.70 (dd, J = 6.3, 7.5 Hz, 2H), 2.01 (dd, J = 6.3, 7.5 Hz, 2H), 1.38 (s, 6H).
79%	With chromium(VI) oxide; tert.-butylhydroperoxide; In dichloromethane; at 20℃; for 8h;	To a solution of 7-bromo-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalene (Compound 15, 1.1 g, 4.62 mmol) in 10 mL of dichloromethane was added chromium (VI) oxide (72 mg, 0.46 mmol) and 5 mL of tert-butyl hydroperoxide solution (TBHP). After stirring at room temperature for 8 h, the mixture was diluted with water (20 mL), extracted with diethyl ether (310 mL), washed with brine (110 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (90:10 hexane/ethyl acetate) yielded the title compound (920 mg, 79percent yield) as a white solid: 1H NMR (CDCl3, 300 MHz) delta 7.87 (d, J=8.1 Hz, 1H), 7.54 (d, J=2.1 Hz, 1H), 7.42 (dd, J=2.1, 8.1 Hz, 1H), 2.70 (dd, J=6.3, 7.5 Hz, 2H), 2.01 (dd, J=6.3, 7.5 Hz, 2H), 1.38 (s, 6H).
53%	With chromium(VI) oxide; In water; acetic acid; for 15h;	c. 6-BROMO-4, 4-DIMETHYL-3, 4-DIHYDRO-2H-NAPHTHALEN-1-ONE A solution of 8.1 g (81 mmol) of chromium trioxide in 74 ml of acetic acid and 3.9 ml of water is added slowly to 14.3 g (60 mmol) of 7-BROM-1, 1- dimethyl-1, 2,3, 4-TETRAHYDRONAPHTHALENE dissolved in 1.5 1 of acetic acid. The reaction medium is stirred for 15 hours, reduced to a volume of 500 ml by concentration, hydrolysed with ice, extracted with ethyl ether and neutralized with 35percent sodium hydroxide solution. The solid obtained is washed with heptane. A pink-white powder is obtained (8 g; 53percent).

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 4345 - 4359.
[2]Patent: WO2005/66115,2005,A2 .Location in patent: Page/Page column 19; 21.
[3]Patent: US2005/148590,2005,A1 .Location in patent: Page/Page column 23; 24.
[4]Tetrahedron,1985,vol. 41,p. 1509 - 1516.
[5]Patent: WO2004/46096,2004,A2 .Location in patent: Page 24.
[6]Patent: US2005/4213,2005,A1 .Location in patent: Page 13.

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[ 98453-60-2 ]
[ 98453-62-4 ]