61348-47-8|2-(Isoxazol-5-yl)phenol| Ambeed

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Quality Control of [ 61348-47-8 ] Purity: 96% SDS Specification

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Product Details of [ 61348-47-8 ]

CAS No. :	61348-47-8
Formula :	C₉H₇NO₂
M.W :	161.16
SMILES Code :	OC1=CC=CC=C1C2=CC=NO2
MDL No. :	MFCD00218653
InChI Key :	DBDXTIAEVFSDNN-UHFFFAOYSA-N
Pubchem ID :	578506

Safety of [ 61348-47-8 ]

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

Computational Chemistry of [ 61348-47-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	11
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	43.96
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.26 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.73
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	1.68
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.05
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.	0.85
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	1.97
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.66

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.51
Solubility	0.498 mg/ml ; 0.00309 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.	-2.27
Solubility	0.873 mg/ml ; 0.00542 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	-3.17
Solubility	0.109 mg/ml ; 0.000678 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	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	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.	-6.09 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)	2.36

Application In Synthesis of [ 61348-47-8 ]

* 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 [ 61348-47-8 ]

[ 61348-47-8 ] Synthesis Path-Downstream 1~35

1
[ 14386-66-4 ]
[ 61348-48-9 ]
[ 61348-47-8 ]

References: [1]Polish Journal of Chemistry,1979,vol. 53,p. 229 - 242.

2
[ 106129-86-6 ]
[ 61348-47-8 ]

Yield	Reaction Conditions	Operation in experiment
5.22 g	With hydroxylamine hydrochloride; In ethanol; at 78℃; for 1h;	To a 100 mL flask was added 15 mL N-methylpyrrolidone, 1-(2-hydroxyphenyl) ethanone (5.03 g, 36.87mmol) and dimethoxy-N,N-dimethylmethanamine (6.21 g, 52.15 mmol) at room temperature. Thereaction mixture was heated to 90 C, stirred at 90 C for 40 min, then cooled to room temperature.Ethanol (50 mL) and hydroxylamine hydrochloride (3.84 g, 55.19 mmol) were added, then the solutionwas heated to 78 C and stirred for 1 h. The reaction mixture was concentrated. The residue washeated to 45 C, then, 125 mL water was added dropwise over 0.5 h. The solution was stirred at 45 Cfor 30 min, then cooled to room temperature and stirred overnight before the solid was collected byfiltration, washed with 20 mL water and dried in an evaporator at 50 C for 4 h to afford 2-(isoxazol-5-yl)phenol as a white solid 5.22 g, (87.7%).

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3630 - 3632.
[2]Tetrahedron Letters,2018,vol. 59,p. 2788 - 2792.
[3]Journal of Heterocyclic Chemistry,2014,vol. 51,p. 1675 - 1678.
[4]Journal of Heterocyclic Chemistry,1977,vol. 14,p. 345 - 347.
[5]Synthesis,2015,vol. 47,p. 235 - 241.
[6]Supramolecular Chemistry,2019,vol. 31,p. 1 - 8.
[7]Journal of Organic Chemistry,2019,vol. 84,p. 13967 - 13974.

3
[ 39079-62-4 ]
[ 61348-47-8 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 4419 - 4424.
[2]Polish Journal of Chemistry,1982,vol. 56,p. 501 - 509.

4
[ 67-56-1 ]
[ 491-38-3 ]
[ 61348-47-8 ]
[ 61348-46-7 ]
[ 86176-53-6 ]

References: [1]Tetrahedron,1986,vol. 42,p. 4215 - 4222.

5
[ 491-38-3 ]
[ 61348-48-9 ]
[ 61348-47-8 ]
[ 61348-46-7 ]
[ 86176-53-6 ]

References: [1]Tetrahedron Letters,1982,vol. 23,p. 5347 - 5350.

6
[ 491-38-3 ]
[ 61348-48-9 ]
[ 61348-47-8 ]
[ 61348-46-7 ]
[ 86176-53-6 ]
[ 86176-46-7 ]

References: [1]Tetrahedron Letters,1982,vol. 23,p. 5347 - 5350.

7
[ 491-38-3 ]
[ 61348-47-8 ]
[ 61348-46-7 ]
[ 86176-53-6 ]

References: [1]Tetrahedron,1986,vol. 42,p. 4215 - 4222.
[2]Tetrahedron,1986,vol. 42,p. 4215 - 4222.
[3]Tetrahedron,1986,vol. 42,p. 4215 - 4222.

8
[ 61348-47-8 ]
[ 6722-08-3 ]

References: [1]Acta Chimica Academiae Scientiarum Hungaricae,1980,vol. 103,p. 271 - 279.

9
[ 61348-47-8 ]
[ 6722-08-3 ]
[ 10523-47-4 ]

References: [1]Acta Chimica Academiae Scientiarum Hungaricae,1980,vol. 103,p. 271 - 279.

10
[ 66665-80-3 ]
[ 61348-47-8 ]

References: [1]Acta Chimica Academiae Scientiarum Hungaricae,1980,vol. 103,p. 271 - 279.

11
[ 14386-66-4 ]
[ 61348-47-8 ]

References: [1]Journal of Chemical Research, Miniprint,1986,p. 1101 - 1127.

12
5-(2-Hydroxy-phenyl)-4,5-dihydro-isoxazol-5-ol [ No CAS ]
[ 61348-47-8 ]

References: [1]Acta Chimica Hungarica,1984,vol. 115,p. 331 - 334.

13
[ 84200-61-3 ]
[ 61348-47-8 ]

References: [1]Archiv der Pharmazie,1984,vol. 317,p. 15 - 21.

14
[ 61348-47-8 ]
[ 38518-76-2 ]

Yield	Reaction Conditions	Operation in experiment
87.3%	With potassium carbonate; In ethanol; water; at 75℃; for 19h;	To a 250 mL flask was added 2-(isoxazol-5-yl)-3-methoxyphenol (5.02 g, 31.15 mmol), potassiumcarbonate (6.03 g, 43.63 mmol), ethanol (50 mL), and water (25 mL) at room temperature. Thereaction mixture was heated to 90 oC (oil bath temperature) and stirred for 19 h. The solution wasconcentrated, then, dichloromethane (50 mL) was added. The solution was stirred at roomtemperature for 1 h, then, filtered. The solid product was washed with water (2.5 mL) anddichloromethane (25 mL) then dried in an evaporator at 50 C to afford 2-amino-5-methoxy-4Hchromen-4-one (4.38 g, 87.3% yield) as a light yellow solid.

References: [1]Synthesis,2015,vol. 47,p. 235 - 241.
[2]Synthesis,2005,p. 1845 - 1849.
[3]Tetrahedron Letters,2018,vol. 59,p. 2788 - 2792.
[4]Supramolecular Chemistry,2019,vol. 31,p. 1 - 8.
[5]Journal of Organic Chemistry,2019,vol. 84,p. 13967 - 13974.

15
[ 118-93-4 ]
[ 61348-47-8 ]

References: [1]Synthesis,2005,p. 1845 - 1849.
[2]Journal of Heterocyclic Chemistry,2014,vol. 51,p. 1675 - 1678.
[3]Synthesis,2015,vol. 47,p. 235 - 241.
[4]Tetrahedron Letters,2018,vol. 59,p. 2788 - 2792.
[5]Journal of Organic Chemistry,2019,vol. 84,p. 13967 - 13974.

16
[ 61348-47-8 ]
5-[2-(3<i>H</i>-imidazol-4-ylmethoxy)-phenyl]-isoxazole [ No CAS ]

References: [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 3449 - 3452.

17
[ 61348-47-8 ]
[ 10523-47-4 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3630 - 3632.
[2]Tetrahedron Letters,2018,vol. 59,p. 2788 - 2792.
[3]Acta Chimica Academiae Scientiarum Hungaricae,1980,vol. 103,p. 271 - 279.
[4]Acta Chimica Academiae Scientiarum Hungaricae,1980,vol. 103,p. 271 - 279.

18
[ 5382-16-1 ]
[ 52147-97-4 ]
[ 61348-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃;	Triethylamine (8. 0g, 0. [079MOL)] was added to a stirred solution of [E- (3-] styrenesulphonyl chloride [(12.] 0g, 0. [059MOL)] and 4-hydroxypiperidine (8. 0g, 0. [079MOL)] in THF (100ml) at RT. Stirring was continued overnight before the reaction mixture was reduced to low volume and partitioned between EtOAc followed by aqueous 1M [HC1,] saturated [NAHCO3] and brine. The organic fraction was then dried [(NA2SO4)] and evaporated to give a solid product. (12.75g ; 0. 046mol) ; NMR (CDC13) : 1.5-1. 8 (m, 4H), 1.9-2. 1 (m, 2H), 3.0-3. 2 (m, 2H), 3.4-3. 6 (m, 2H), 3.85 (s, 1H), 6.65 (s, 1H), 7.3-7. 6 (m, 6H); MS: 268.

References: [1]Patent: WO2004/6926,2004,A1 .Location in patent: Page/Page column 47.

19
[ 61348-47-8 ]
[ 647014-02-6 ]
[ 647014-03-7 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 20℃;	2- (5-Isoxazolyl)-phenol (121mg, 0. 75mmol) was dissolved in DCM [(LML)] and E-1- (4- [HYDROXYPIPERIDIN-L-YLSULPHONYL)-2-PHENYLETHENE] (0.2g, 0. [75MMOL)] was added. A solution of triphenylphosphine (0.2g, 0.75mmol) in DCM [(2ML)] followed by a solution of DIAD (0. [15ML,] 0. [75MMOL)] in DCM (2ml) was then added and the resulting mixture stirred at RT overnight. The mixture was concentrated and purified by chromatography: bond elute cartridge, eluent hexane (5 minutes; 20 mUminute), 100% hexane to 100% DCM (15 minutes) to give [E- [4- (2-] (5-isoxazolyl) phenyloxy) [PIPERIDIN-1-YLSULPHONYL]-2-PHENYLETHENE,] which was carried through to the next step.

References: [1]Patent: WO2004/6926,2004,A1 .Location in patent: Page/Page column 47.

20
[ 61348-47-8 ]
2-bromo-1-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)ethanone [ No CAS ]
[ 1380732-85-3 ]

References: [1]ChemMedChem,2012,vol. 7,p. 1031 - 1043.

21
[ 61348-47-8 ]
[ 1384106-86-8 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3630 - 3632.
[2]Tetrahedron Letters,2012,vol. 53,p. 3630 - 3632.

22
[ 61348-47-8 ]
[ 1384106-87-9 ]

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3630 - 3632.
[2]Tetrahedron Letters,2012,vol. 53,p. 3630 - 3632.

23
[ 61348-47-8 ]
[ 1384106-88-0 ]