50405-45-3|4-Hydroxy-5,6-dimethyl-2H-pyran-2-one| Ambeed

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Quality Control of [ 50405-45-3 ] Purity: 97% SDS Specification

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Product Details of [ 50405-45-3 ]

CAS No. :	50405-45-3
Formula :	C₇H₈O₃
M.W :	140.14
SMILES Code :	CC1=C(C)C(O)=CC(=O)O1
MDL No. :	MFCD09746192
InChI Key :	FADNXPYGPCOODY-UHFFFAOYSA-N
Pubchem ID :	54712915

Safety of [ 50405-45-3 ]

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

Computational Chemistry of [ 50405-45-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.29
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	36.93
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	50.44 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.56
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	0.43
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.96
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.	0.33
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	1.78
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.01

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.42
Solubility	5.28 mg/ml ; 0.0377 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.	-1.06
Solubility	12.3 mg/ml ; 0.0878 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	-2.11
Solubility	1.09 mg/ml ; 0.0078 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.	-6.85 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)	2.75

Application In Synthesis of [ 50405-45-3 ]

* 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 [ 50405-45-3 ]

[ 50405-45-3 ] Synthesis Path-Downstream 1~35

1
4-Methyl-3,5-dioxo-hexansaeure [ No CAS ]
[ 50405-45-3 ]

Yield	Reaction Conditions	Operation in experiment
2.33 g	With hydrogen fluoride; In diethyl ether; at -20℃;	Compound 5 was synthesized using a modified approach as describe by Wilcox (J. Am. Chem. Soc. 1988, 110,470-481). 3-Methyl-2,4-pentanedione (4.9 g) was reacted with freshly prepared NaNH2 and dry ice to obtain adiketoacid 4. Further treatment of 4 with HF provided the hydroxy pyrone 5 (2.33 g, 39 %) as red crystals. mp209.2-210.5 oC, 1H NMR (400 MHz, Methanol-D4), delta (ppm) 5.39 (s, 1H), 2.23 (s, 3H), 1.91 (s, 3H). 13C NMR(100.53 MHz, Methanol-D4), delta (ppm) 173.4, 168.2, 160.6, 109.4, 89.6, 17.51, 9.56, MS-C7H8O3(140.05), m/z(%): Found 140 (M+)

References: [1]Synthetic Communications,1990,vol. 20,p. 1931 - 1941.
[2]Journal of the American Chemical Society,1984,vol. 106,p. 4186 - 4188.
[3]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 1192 - 1195.

2
[ 75950-51-5 ]
[ 50405-45-3 ]

References: [1]Chemistry - A European Journal,2009,vol. 15,p. 2826 - 2845.
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 2272 - 2277.
[3]Journal of the American Chemical Society,2011,vol. 133,p. 8854 - 8857.
[4]Heterocycles,2000,vol. 53,p. 549 - 552.

3
[ 77-78-1 ]
[ 50405-45-3 ]
[ 64361-40-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; In acetone; for 15h;Inert atmosphere; Reflux;	Synthesis of 4-methoxy-5,6-dimethyl-2-pyrone (6). Hydroxy pyrone (660 mg, 4.7 mmol) and dimethyl sulfate (500 muL, 5.18 mmol) were placed in round bottomflaks along with 10 mL of acetone. Potassium carbonate (4 g, 6 eqv.) was the added and the reaction mixturewas refluxed for 15 h under argon. The reaction mixture was filtered through sintered glass funnel; resultingfiltrate was concentrated and then subjected to flash chromatography. Product eluted with 1:1 mixture ofhexanes and ethyl acetate to get a yellow solid in 81% isolated yield. Yellow solid, mp 101.7-103.0 oC, 1HNMR (400 MHz, CDCl3), delta (ppm) 5.38 (s, 1H), 3.76 (s, 3H), 2.15 (s, 3H), 1.81 (s, 3H). 13C NMR (100.53MHz, CDCl3), delta (ppm) 170.9, 164.6, 157.6, 106.8, 87.8, 56.0, 17.2, 9.4, MS-C8H10O3(154.06), m/z (%): Found154 (M+)

References: [1]Tetrahedron Letters,1985,vol. 26,p. 4789 - 4792.
[2]Journal of the Chemical Society. Perkin transactions I,1991,p. 1941 - 1945.
[3]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 1192 - 1195.
[4]Journal of the American Chemical Society,1984,vol. 106,p. 4186 - 4188.

5
[ 50-00-0 ]
[ 50405-45-3 ]
[ 57103-53-4 ]

References: [1]Heterocycles,2000,vol. 53,p. 549 - 552.

6
[ 50405-45-3 ]
(1S,6R)-1,3,3-Trimethyl-2-methylene-7-oxa-bicyclo[4.1.0]heptane [ No CAS ]
[ 28354-98-5 ]
4,4-dimethyl-2,3-dimethylenecyclohanol [ No CAS ]
C₁₇H₂₂O₃ [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 1713 - 1716.
[2]Tetrahedron Letters,2002,vol. 43,p. 1713 - 1716.
[3]Tetrahedron Letters,2002,vol. 43,p. 1713 - 1716.

7
[ 50405-45-3 ]
(1S,6R)-1,3,3-Trimethyl-2-methylene-7-oxa-bicyclo[4.1.0]heptane [ No CAS ]
4-hydroxy-3-(3-hydroxy-2,6,6-trimethyl-cyclohex-1-enylmethyl)-5,6-dimethyl-pyran-2-one [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 1713 - 1716.

8
[ 50405-45-3 ]
C₂₂H₃₄O₃ [ No CAS ]
C₂₂H₃₄O₃ [ No CAS ]
C₂₉H₄₀O₅ [ No CAS ]
C₂₉H₄₀O₅ [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 5235 - 5238.
[2]Tetrahedron Letters,2003,vol. 44,p. 5235 - 5238.

9
[ 50405-45-3 ]
3-bromo-4-hydroxy-5,6-dimethyl-2H-pyran-2-one [ No CAS ]