10521-08-1|2H-Pyran-2,4,6(3H,5H)-trione| Ambeed

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Quality Control of [ 10521-08-1 ] Purity: 95% SDS Specification

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Product Details of [ 10521-08-1 ]

CAS No. :	10521-08-1
Formula :	C₅H₄O₄
M.W :	128.08
SMILES Code :	O=C1CC(CC(O1)=O)=O
MDL No. :	MFCD07783094
InChI Key :	UNBPFPUTIKOOOI-UHFFFAOYSA-N
Pubchem ID :	12439073

Safety of [ 10521-08-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 10521-08-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	0
Fraction Csp3	0.4
Num. rotatable bonds	0
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	25.72
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	60.44 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.27
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	-0.25
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.58
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.	-0.62
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	0.95
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.05

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.48
Solubility	42.7 mg/ml ; 0.334 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.	-0.56
Solubility	35.2 mg/ml ; 0.275 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	-0.64
Solubility	29.6 mg/ml ; 0.231 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	No
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.	-7.26 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	2.0 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)	1.49

Application In Synthesis of [ 10521-08-1 ]

* 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 [ 10521-08-1 ]

[ 10521-08-1 ] Synthesis Path-Downstream 1~35

1
[ 10521-08-1 ]
[ 127-09-3 ]
[ 100-34-5 ]
3-oxo-2-phenylhydrazono-glutaric acid-anhydride [ No CAS ]

References: [1]Roczniki Chemii,vol. 6,p. 28.
Chemisches Zentralblatt,1926,vol. 97,p. 2907.

2
[ 10521-08-1 ]
[ 108-24-7 ]
[ 33524-90-2 ]

References: [1]Journal of the Chemical Society C: Organic,1971,p. 2721 - 2726.

3
[ 10521-08-1 ]
[ 78315-99-8 ]

References: [1]Journal of Organic Chemistry,1957,vol. 22,p. 1385,1388, 1392.
Journal of Organic Chemistry,1958,vol. 23,p. 391,393.

4
[ 542-05-2 ]
[ 10521-08-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With acetic anhydride; In acetic acid; at 0 - 10℃; for 3.0h;	EXAMPLE 27 6(7)-Hydroxy-2-methoxycarbonyl-8-azabicyclo(3.2.1)octane-2-one; and 6(7)-methoxy-2-methoxycarbonyl-8-azabicyclo(3.2.1)octane-2-one; To a solution of 60 ml of acetic acid and 43 ml of acetic anhydride at 0 C., was added slowly 40 g (0.27 mol) of acetonedicarboxylic acid.. The mixture was stirred and the temperature was not allowed to rise above 10 C. The acid was dissolved slowly and a pale yellow precipitate formed.. After 3 h the product was filtered, washed with 30 ml of glacial acetic acid and 100 ml of benzene.. The white powder obtained was dried at high vacuum to afford 30 g of acetonedicarboxylic acid anhydride (yield 86%)..

References: [1]Asian Journal of Chemistry,2014,vol. 26,p. 7867 - 7868.
[2]Tetrahedron Letters,1982,vol. 23,p. 1971 - 1974.
[3]Journal of Medicinal Chemistry,2001,vol. 44,p. 2619 - 2635.
[4]Patent: US6353105,2002,B1 .Location in patent: Page column 23.
[5]Organic Letters,2011,vol. 13,p. 3876 - 3879.
[6]Organic Letters,2016,vol. 18,p. 5580 - 5583.
[7]Journal of Organic Chemistry,1983,vol. 48,p. 2379 - 2383.
[8]Organic process research and development,2011,vol. 15,p. 503 - 514.
[9]Roczniki Chemii,vol. 6,p. 28.
Chemisches Zentralblatt,1926,vol. 97,p. 2907.
[10]Tetrahedron Letters,1997,vol. 38,p. 1121 - 1124.

5
[ 542-05-2 ]
[ 108-24-7 ]
[ 10521-08-1 ]
[ 33524-90-2 ]
[ 33524-88-8 ]
[ 10386-63-7 ]

References: [1]Journal of the Chemical Society C: Organic,1971,p. 2721 - 2726.

6
[ 10521-08-1 ]
[ 137-07-5 ]
[ 17822-28-5 ]

References: [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 498 - 501.
Zhurnal Obshchei Khimii,1962,vol. 32,p. 506 - 510.

7
[ 186581-53-3 ]
[ 10521-08-1 ]
[ 21249-83-2 ]

References: [1]Tetrahedron Letters,1982,vol. 23,p. 1971 - 1974.

8
[ 1121-60-4 ]
[ 67-56-1 ]
[ 10521-08-1 ]
[ 2516-47-4 ]
N-Cyclopropylmethyl-2,6-di<2>pyridyl-4-piperidon-3-carbonsaeuremethylester [ No CAS ]

References: [1]Archiv der Pharmazie,1988,vol. 321,p. 917 - 920.

9
[ 1121-60-4 ]
[ 67-56-1 ]
[ 10521-08-1 ]
[ 89-97-4 ]
N-(2-Chlorbenzyl)-2,6-di<2>pyridyl-4-piperidon-3-carbonsaeuremethylester [ No CAS ]

References: [1]Archiv der Pharmazie,1988,vol. 321,p. 917 - 920.

10
[ 67-56-1 ]
[ 10521-08-1 ]
[ 78315-99-8 ]

Yield	Reaction Conditions	Operation in experiment
	for 1.0h;	To a flask containing 50 g (0.39 mol) of <strong>[10521-08-1]acetonedicarboxylic acid anhydride</strong> was added 160 ml of cold dry MeOH. The monomethylester solution was allowed to stand for 1 h and filtered.. The filtrate of acetonedicarboxylic acid monomethyl ester was used directly in the following condensation reaction.
		20 mmol of <strong>[10521-08-1]2,4,6-trioxotetrahydropyrane</strong> were stirred in 30 mL methanol till dissolution and afterwards cooled to -20 C. 20 mmol of the corresponding amine and 40 mmol pyridine-2-carboxaldehyde dissolved in 20 mL methanol, respectively, were added to the solution in parallel in a way that the reaction temperature does not exceed - 20 C. After stirring for 2 h at -10 C the solvent was removed in vacuo at room temperature. The obtained residue was covered with a small amount of methanol and the product crystallized at 4 C. The analytical and spectroscopic data of 19-24 are in accordance with the ref. 30,31,32,33 Methyl (2'R,6'S)-1'-benzyl-4'-hydroxy-1',2',5',6'-tetrahydro-2,2';6',2''-terpyridine-3'-carboxylate (19): C24H23N3O3 (401.5 g/mol), yield: 33% (53%)31, mp. 155 C (163-164).33
	at 5 - 20℃;	<strong>[10521-08-1]acetonedicarboxylic acid anhydride</strong> (31.4 kg) was added to methanol (100 L) cooled to 5 C. upon vigorous stirring. The resulting solution was kept at ambient temperature for 45 min to ensure that formation of acetone dicarboxylic acid monomethyl ester was complete.

References: [1]Organic Letters,2016,vol. 18,p. 5580 - 5583.
[2]Journal of Organic Chemistry,1983,vol. 48,p. 2379 - 2383.
[3]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 2762 - 2768.
[4]Archiv der Pharmazie,1988,vol. 321,p. 917 - 920.
[5]Tetrahedron Letters,1997,vol. 38,p. 1121 - 1124.
[6]Journal of Medicinal Chemistry,2001,vol. 44,p. 2619 - 2635.
[7]European Journal of Medicinal Chemistry,2005,vol. 40,p. 299 - 304.
[8]Patent: US6353105,2002,B1 .Location in patent: Page column 23.
[9]Journal of Medicinal Chemistry,2008,vol. 51,p. 238 - 250.
[10]Patent: EP2036556,2009,A1 .Location in patent: Page/Page column 11.
[11]Patent: US7855296,2010,B1 .Location in patent: Page/Page column 8.

11
[ 10521-08-1 ]
[ 71-43-2 ]
[ 5526-43-2 ]

References: [1]Synthetic Communications,1989,vol. 19,p. 2453 - 2460.

12
[ 10521-08-1 ]
[ 128243-43-6 ]

References: [1]Angewandte Chemie,1990,vol. 102,p. 920 - 923.

17
[ 10521-08-1 ]
[ 79-22-1 ]
methyl 2-hydroxy-4-(methoxycarbonyloxy)-6-oxo-6H-pyran-3-carboxylate [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 9152 - 9162.

18
[ 10521-08-1 ]
6-exo,8-dimethyl-3-hydroxy-8-aza-bicyclo[3.2.1]-octane-2-carboxylic acid methyl ester [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2005,vol. 40,p. 299 - 304.

19
[ 10521-08-1 ]
7-exo,8-dimethyl-8-aza-bicyclo[3.2.1]-oct-2-ene-2-carboxylic acid methyl ester [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2005,vol. 40,p. 299 - 304.

20
[ 10521-08-1 ]
[ 5526-38-5 ]

References: [1]Synthetic Communications,1989,vol. 19,p. 2453 - 2460.

21
[ 10521-08-1 ]
[ 4225-45-0 ]

References: [1]Synthetic Communications,1989,vol. 19,p. 2453 - 2460.

22
[ 10521-08-1 ]
[ 80601-62-3 ]

References: [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 2762 - 2768.

23
[ 10521-08-1 ]
[ 85850-13-1 ]