1081-30-7|Methyl 3-phenylisoxazole-5-carboxylate| Ambeed

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Quality Control of [ 1081-30-7 ] Purity: 97% SDS Specification

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Product Details of [ 1081-30-7 ]

CAS No. :	1081-30-7
Formula :	C₁₁H₉NO₃
M.W :	203.19
SMILES Code :	O=C(C1=CC(C2=CC=CC=C2)=NO1)OC
MDL No. :	MFCD00837810
InChI Key :	SSDKYDGBJLXLAO-UHFFFAOYSA-N
Pubchem ID :	827498

Safety of [ 1081-30-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 1081-30-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	11
Fraction Csp3	0.09
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	53.22
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.33 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.33
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	2.22
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.13
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.	1.33
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	2.27
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.05

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.84
Solubility	0.292 mg/ml ; 0.00144 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.	-2.95
Solubility	0.226 mg/ml ; 0.00111 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	-3.84
Solubility	0.0295 mg/ml ; 0.000145 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.	-5.96 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)	2.66

Application In Synthesis of [ 1081-30-7 ]

* 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 [ 1081-30-7 ]

[ 1081-30-7 ] Synthesis Path-Downstream 1~35

1
[ 922-67-8 ]
[ 698-16-8 ]
[ 1081-30-7 ]

References: [1]Chemische Berichte,1973,vol. 106,p. 3275 - 3290.

2
[ 1081-30-7 ]
[ 14442-12-7 ]

Yield	Reaction Conditions	Operation in experiment
80%		To a stirred solution of alkyl ester (1 equivalent) in dioxane was added aqueous NaOH (1N, 1.5 to 10 equivalents). This mixture was stirred until TLC analysis indicated completion of the reaction (usually 30 mins to 16 h) at which time the reaction was extracted with ether. The resulting aqueous layer was separated, acidified by additional of 1N HCl to pH 4. If there was a formation of solid, the solid was filtered, washed with water and air dried to obtain pure acid. Otherwise, the acidified aqueous layer was extracted with EtOAc, the organic layer was dried over Na2SO4, concentrated under reduced pressure to yield pure acid; 3-Phenylisoxazole-5-carboxylic acid was prepared from 3-phenylisoxazole-5-carboxylic acid methyl ester according to Method C in 80% yield using LiOH as a base and 1:1 mixture of MEOH:THF as a solvent.
2.2 g	With sodium hydroxide; In 1,4-dioxane; at 25℃; for 2h;	To a stirred solution of methyl 3-phenylisoxazole-5- carboxylate (4.5g, 19.80mmol) in l,4-dioxane(40mL) was added I aOH (21.12mL) added drop wise at 0C. The reaction mixture was stirred for 2h at 25C. Dioxane was distilled off and the crude mixture was diluted with water (20mL) and acidified using IN HC1 (25mL).The resulting precipitate was filtered, washed with water and dried under vacuum to obtain 3-phenylisoxazole-5-carboxylic acid (2.2g).

References: [1]Patent: US2006/211603,2006,A1 .Location in patent: Page/Page column 39; 48.
[2]Chemische Berichte,1973,vol. 106,p. 3275 - 3290.
[3]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6218 - 6221.
[4]Patent: WO2016/54560,2016,A1 .Location in patent: Page/Page column 46.

3
[ 908094-01-9 ]
[ 14442-12-7 ]
[ 1081-30-7 ]

References: [1]Canadian Journal of Chemistry,1980,vol. 58,p. 1144 - 1150.

4
[ 873-67-6 ]
[ 52745-92-3 ]
[ 50899-16-6 ]
[ 1081-30-7 ]

References: [1]Polish Journal of Chemistry,1982,vol. 56,p. 257 - 266.

5
[ 102-06-7 ]
[ 1081-30-7 ]
[ 103912-54-5 ]
[ 103912-53-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 1871 - 1874.

6
[ 110-89-4 ]
[ 1081-30-7 ]
(3-Phenyl-isoxazol-5-yl)-piperidin-1-yl-methanone [ No CAS ]

References: [1]Archiv der Pharmazie,1995,vol. 328,p. 437 - 443.

7
[ 110-91-8 ]
[ 1081-30-7 ]
Morpholin-4-yl-(3-phenyl-isoxazol-5-yl)-methanone [ No CAS ]

References: [1]Archiv der Pharmazie,1995,vol. 328,p. 437 - 443.

8
[ 124-40-3 ]
[ 1081-30-7 ]
3-Phenyl-isoxazole-5-carboxylic acid dimethylamide [ No CAS ]

References: [1]Archiv der Pharmazie,1995,vol. 328,p. 437 - 443.

9
methyl 4-phenyl-2-oxo-4-hydroximinobutyrate [ No CAS ]
[ 1081-30-7 ]

References: [1]Archiv der Pharmazie,1995,vol. 328,p. 437 - 443.

10
[ 110-68-9 ]
[ 1081-30-7 ]
3-Phenyl-isoxazole-5-carboxylic acid butyl-methyl-amide [ No CAS ]

References: [1]Archiv der Pharmazie,1995,vol. 328,p. 437 - 443.

12
[ 922-67-8 ]
[ 698-16-8 ]
[ 50899-16-6 ]
[ 1081-30-7 ]

References: [1]Chemistry - A European Journal,2006,vol. 12,p. 1156 - 1161.

13
[ 4519-46-4 ]
[ 934-16-7 ]
[ 1081-30-7 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 1295 - 1298.

14
[ 1821-34-7 ]
[ 1081-30-7 ]

References: [1]Polish Journal of Chemistry,1982,vol. 56,p. 257 - 266.

15
[ 873-67-6 ]
1<i>t</i>-<3-nitro-phenyl>-buta-1,3-diene [ No CAS ]
[ 1081-30-7 ]

References: [1]Canadian Journal of Chemistry,1980,vol. 58,p. 1144 - 1150.

16
[ 75025-16-0 ]
[ 1081-30-7 ]

References: [1]Canadian Journal of Chemistry,1980,vol. 58,p. 1144 - 1150.

17
[ 698-16-8 ]
sodium-compound of 4,4-dimethyl-3-oxo-valeric acid ethyl ester [ No CAS ]
[ 1081-30-7 ]

References: [1]Canadian Journal of Chemistry,1980,vol. 58,p. 1144 - 1150.

18
[ 1081-30-7 ]
[ 103912-53-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 1871 - 1874.

19
[ 1081-30-7 ]
[ 103912-65-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 1871 - 1874.
[2]Journal of the Chemical Society. Perkin transactions I,1985,p. 1871 - 1874.

20
[ 922-67-8 ]
[ 932-90-1 ]
[ 1081-30-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With Oxone; potassium chloride; In water; at 20℃; for 3h;Green chemistry;	General procedure: Aldoxime 1 (0.5 mmol),alkene 2 (1.25 mmol) and KCl (0.5 mmol) were added to a flask carefully,then water (3 ml) was added, finally Oxone (0.75 mmol) was added in stirring. The mixture was stirred at room temperature for 3 h till the reaction was complete.The mixture was poured into a separating funnel, and the flask was wash with 4ml CH2Cl2. Extraction of the mixture with CH2Cl2 (2×4mL) and the combined organic phase wasdried over anhydrous Na2SO4, filtered, and concentratedunder reduced pressure. The residue was purified on a silica gel plate withThin-Layer Chromatography technique (10:1 petroleum ether-EtOAc) to provide thecorresponding pure isoxazoline 3
77%	With [bis(acetoxy)iodo]benzene; In water; acetonitrile; at 0℃; for 0.25h;	General procedure: A mixture of benzaldehyde oxime derivative (1, 0.5 mmol, 1 equiv) and 1.5 equiv of dialkylacetylenedicarboxylate (3 or 4) or methyl propiolate (5), dissolved in 6 mL of a 2:1 acetonitrile/water mixture. To this diacetoxyiodobenzene (DIB) (0.60 mmol, 1.2 equiv) solution in 4 mL water was added drop wise over a period of 5 min at 0 C. After complete addition of DIB, the reaction was monitored by TLC at regular time intervals. After completion of the reaction (additional 5-10 min), the reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate and washed with water and extracted thrice with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude mixture was purified by silica gel column chromatography using 5-10% ethyl acetate in hexanes as eluent to obtain pure isoxazole compound.
48%	With sodium hypochlorite; In dichloromethane; at 20℃; for 1h;	To a stirred mixture of oxime (30 mmol) and methyl propiolate (10 mL) in dichloromethane (200 mL) was added Chlorax (100 mL) dropwise. The resultant reaction mixture was stirred at room temperature for an additional 1 h (initially the reaction was exothermic). The reaction mixture was diluted with dichloromethane (200 mL), the organic layer was separated, dried over MgSO4, and concentrated in vacuo; 3-Phenylisoxazole-5-carboxylic acid methyl ester was prepared from benzaldehyde oxime and methyl propiolate according to Method K in 48% yield after purification by silica gel column chromatography using hexane/ethyl acetate mixture (8:2) as an eluent.

References: [1]Tetrahedron Letters,2014,vol. 55,p. 2308 - 2311.
[2]Tetrahedron Letters,2016,vol. 57,p. 719 - 722.
[3]Patent: US2006/211603,2006,A1 .Location in patent: Page/Page column 39; 48.
[4]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6218 - 6221.

21
[ 922-67-8 ]
[ 932-90-1 ]
[ 50899-16-6 ]
[ 100-52-7 ]
[ 1081-30-7 ]

References: [1]Molecules,2008,vol. 13,p. 1230 - 1237.

22
[ 1729-67-5 ]
[ 81745-44-0 ]
[ 1081-30-7 ]

References: [1]Synlett,2008,p. 919 - 923.

23
[ 922-67-8 ]
[ 932-90-1 ]
[ 50899-16-6 ]
[ 1081-30-7 ]

References: [1]Organic Letters,2011,vol. 13,p. 2966 - 2969.

24
C₂₄H₁₈NO₄Pol [ No CAS ]
[ 1081-30-7 ]

References: [1]Synthetic Communications,2012,vol. 42,p. 3279 - 3287.

25
[ 67-56-1 ]
C₁₀H₆NO₃Pol [ No CAS ]
[ 1081-30-7 ]

References: [1]Heteroatom Chemistry,2012,vol. 23,p. 444 - 448.

26
[ 1081-30-7 ]
methyl 5-(3-phenylisoxazole-5-carboxamido)pentanoate [ No CAS ]