5027-32-7|3,4-Diacetylhexane-2,5-dione| Ambeed

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Quality Control of [ 5027-32-7 ] Purity: 95% SDS Specification

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Product Details of [ 5027-32-7 ]

CAS No. :	5027-32-7
Formula :	C₁₀H₁₄O₄
M.W :	198.22
SMILES Code :	CC(C(C(C)=O)C(C(C)=O)C(C)=O)=O
MDL No. :	MFCD00031531
InChI Key :	CSKRBHOAJUMOKJ-UHFFFAOYSA-N
Pubchem ID :	78730

Safety of [ 5027-32-7 ]

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 [ 5027-32-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	0
Fraction Csp3	0.6
Num. rotatable bonds	5
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	50.98
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	68.28 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.68
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	-0.56
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.57
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.	-0.26
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	1.67
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.62

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.39
Solubility	81.5 mg/ml ; 0.411 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.	-0.4
Solubility	78.2 mg/ml ; 0.394 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	-1.33
Solubility	9.36 mg/ml ; 0.0472 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.	-7.91 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	1.0 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)	1.34

Application In Synthesis of [ 5027-32-7 ]

* 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 [ 5027-32-7 ]

[ 5027-32-7 ] Synthesis Path-Downstream 1~35

1
[ 5027-32-7 ]
[ 4054-67-5 ]

References: [1]CrystEngComm,2013,vol. 15,p. 8280 - 8287.
[2]Journal of the Chemical Society, Dalton Transactions,2000,p. 713 - 718.
[3]Journal of the Chemical Society,1957,p. 3997,4000.
[4]New Journal of Chemistry,2004,vol. 28,p. 756 - 759.

2
[ 5027-32-7 ]
[ 10599-72-1 ]

Yield	Reaction Conditions	Operation in experiment
87.6%	With potassium hydrogensulfate; In 5,5-dimethyl-1,3-cyclohexadiene;Heating;	action apparatus was a 2000 ml four-neck round bottom flask equipped with a thermometer, a mechanical stirrer, a water separator, a condenser, and a silicone oil bath.The four-necked round bottom flask was placed in a silicone oil bath, and the thermometer and water separator were mounted on a four-neck round bottom flask. The condenser was installed at the upper end of the water separator, and 198 g of 3 was placed in a 2000 ml four-neck round bottom flask. 4-diacetyl-2,5-hexanedione, 1000ml of xylene and 6.8g of potassium hydrogen sulfate, start stirring with a stirrer, warm the water in a silicone oil bath and return to water until no water is released, stop heating, cool to room temperature, filter The catalyst was removed, and the filtrate was evaporated under reduced pressure to dryness crystals crystals crystals crystals 87.6%, the mother liquor is applied later.
68%	With titanium tetrachloride; In toluene; at 80℃;Inert atmosphere;	In a 50 mL two-necked flask equipped with a reflux condenser and under the protection of nitrogen,Add freshly distilled toluene(20 mL), tetracarbonyl compound 1a (5 mmol) and titanium tetrachloride (10 mmol).Heated to 80 C with stirring for 0.5-2 hours,The reaction was monitored continuously by TLC, quenched by addition of saturated aqueous ammonium chloride (10 mL)Two-phase solution was obtained.A separatory funnel was used to separate the upper toluene solution,The lower aqueous solution was extracted with dichloromethane (3 × 10 mL).The resulting toluene and methylene chloride solution were combined,Dried over anhydrous sodium sulfate and concentrated under reduced pressure,Directly silica gel column chromatography,Furan IIa was obtained as a yellow oil in 68% yield.
	In hydrogenchloride;	A mixture of 1.0 g. of 1,1,2,2-tetraacetylethane in 10 ml. of concentrated hydrochloric acid was stirred at room temperature for about 1 hour until a clear solution was obtained. The mixture was then poured onto ice and extracted with diethyl ether. The extracts were dried over sodium sulfate, taken to dryness, and the residue recrystallized from hexane to give 2,5-dimethyl-3,4-diacetylfuran, m.p. 75-77 C.

References: [1]Patent: CN109824633,2019,A .Location in patent: Paragraph 0036-0039; 0047; 0055; 0063.
[2]Patent: CN107311963,2017,A .Location in patent: Paragraph 0025; 0026; 0027.
[3]Gazzetta Chimica Italiana,1893,vol. 23 II,p. 307.
[4]American Chemical Journal,1893,vol. 15,p. 527.
[5]Journal of the Chemical Society,1924,vol. 125,p. 751.
[6]Journal of the Chemical Society,1956,p. 319,323.
[7]Patent: US4000165,1976,A .

3
[ 1118-67-8 ]
[ 5027-32-7 ]

References: [1]CrystEngComm,2013,vol. 15,p. 8280 - 8287.
[2]Chemische Berichte,1914,vol. 47,p. 3338.

4
[ 5027-32-7 ]
[ 74-89-5 ]
[ 55341-97-4 ]

References: [1]Journal of the American Chemical Society,1957,vol. 79,p. 3200,3202.

5
[ 123-54-6 ]
[ 5027-32-7 ]

Yield	Reaction Conditions	Operation in experiment
65%		A three-necked 1 litre round-bottomed flask under an inert atmosphere (nitrogen) was charged with sodium tert-butoxide (30.0g, 310mmol) and a magnetic stirrer-bar. Thf (dried and distilled over Na/benzophenone, 500mL) was introduced, the temperature reducedto-78C and pentane-2,4-dione (30.0g,300mmol) in Thf (dried and distilled over Nalbenzophenone, 100mL) added over 30 min. The reaction was allowed to warm to around 0C and cooled with an ice-bath to maintain the temperature below 5C. Iodine (38.0g, 150mmol) in Thf (dried and distilled over Na/benzophenone, 100mL) was added dropwise. The reaction mixture was stirred for a further 30 min. with the ice-bath and then for 1 hour once the ice-bath had been removed. Diethylether (300mL) was added to the reaction mixture, which was then poured into 200mL saturated ammonium chloride solution (the pH was measured to ensure that the product had been neutralised). The organic layer was washed with 0.25M sodium thiosulfate solution (2 x 200mL) and then brine(200mL). The volatiles were removed in vacuo and the product recrystallised from ethanol(95%) to yield colourless crystals (19.3g, 65%). M. p.193-4C. The product was used without further purification.
	With iodine; In diethyl ether; mineral oil;	EXAMPLE To a slurry of 84.5 g. (2.0 moles) of a 57% mineral oil dispersion of sodium hydride in 1500 ml. of diethyl ether was added a solution of 200 ml. (2.0 moles) of 2,4-pentanedione in 200 ml. of diethyl ether over a period of two and one half hours. The mixture was stirred an additional thirty minutes, and then treated dropwise with a solution of 254 g. (1.0 mole) of iodine in about 2 liters of diethyl ether over a period of 6 hours. The mixture was allowed to stand overnight, and the solid which separated was then collected, washed once with diethyl ether, once with water, and dried to give 114.1 g. of 1,1,2,2-tetraacetylethane, m.p. 186-206 C.

References: [1]Synthetic Communications,2007,vol. 37,p. 4399 - 4405.
[2]Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.),1992,vol. 41,p. 123 - 126.
    Izvestiya Akademi Nauk, Seriya Khimicheskaya,1992,p. 154 - 158.
[3]Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.),1992,vol. 41,p. 123 - 126.
    Izvestiya Akademi Nauk, Seriya Khimicheskaya,1992,p. 154 - 158.
[4]Tetrahedron Letters,1995,vol. 36,p. 8757 - 8760.
[5]Synthetic Communications,2010,vol. 40,p. 1847 - 1855.
[6]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 2535 - 2540.
[7]Tetrahedron,1988,vol. 44,p. 1603 - 1608.
[8]Journal of the Chemical Society, Dalton Transactions,2000,p. 713 - 718.
[9]Patent: WO2004/58783,2004,A1 .Location in patent: Page/Page column 18-19.
[10]Doklady Chemistry,1983,vol. 268,p. 20 - 22.
    Dokl. Akad. Nauk SSSR Ser. Khim.,1983,vol. 268,p. 625 - 627.
[11]Russian Journal of Organic Chemistry,2005,vol. 41,p. 134 - 140.
[12]Doklady Chemistry,1984,vol. 278,p. 347 - 350.
    Dokl. Akad. Nauk SSSR Ser. Khim.,1984,vol. 278,p. 1127 - 1130.
[13]American Chemical Journal,1893,vol. 15,p. 527.
[14]Journal of the American Chemical Society,1948,vol. 70,p. 1271.
[15]Justus Liebigs Annalen der Chemie,1961,vol. 641,p. 40 - 50.
[16]Acta Chemica Scandinavica (1947),1971,vol. 25,p. 1576 - 1582.
[17]Chemical Communications (London),1966,p. 325.
[18]Journal of Organic Chemistry USSR (English Translation),1978,vol. 14,p. 34 - 36.
    Zhurnal Organicheskoi Khimii,1978,vol. 14,p. 39 - 42.
[19]Journal of the Chemical Society, Dalton Transactions,1983,p. 2561 - 2562.
[20]Doklady Chemistry,1984,vol. 278,p. 347 - 350.
    Dokl. Akad. Nauk SSSR Ser. Khim.,1984,vol. 278,p. 1127 - 1130.
[21]Journal of general chemistry of the USSR,1988,vol. 58,p. 139 - 146.
    Zhurnal Obshchei Khimii,1988,vol. 58,p. 157 - 165.
[22]New Journal of Chemistry,2004,vol. 28,p. 756 - 759.
[23]Chemistry Letters,2008,vol. 37,p. 716 - 717.
[24]Patent: US4000165,1976,A .
[25]Inorganic Chemistry,2021,vol. 60,p. 13136 - 13149.

6
[ 5027-32-7 ]
[ 38604-92-1 ]

References: [1]Gazzetta Chimica Italiana,1964,vol. 94,p. 393 - 401.
[2]Gazzetta Chimica Italiana,1964,vol. 94,p. 393 - 401.

7
[ 5027-32-7 ]
[ 40801-11-4 ]

References: [1]Australian Journal of Chemistry,1982,vol. 35,p. 1185 - 1201.

8
[ 108-88-3 ]
[ 123-54-6 ]
[ 5027-32-7 ]
[ 32210-62-1 ]

References: [1]Bulletin de la Societe Chimique de France,1987,p. 438 - 440.

9
[ 91-20-3 ]
[ 123-54-6 ]
[ 5027-32-7 ]
[ 94106-16-8 ]

References: [1]Bulletin de la Societe Chimique de France,1987,p. 438 - 440.

10
[ 95-47-6 ]
[ 123-54-6 ]
[ 5027-32-7 ]
[ 115241-30-0 ]

References: [1]Bulletin de la Societe Chimique de France,1987,p. 438 - 440.

11
[ 120-12-7 ]
[ 123-54-6 ]
[ 5027-32-7 ]
[ 111982-85-5 ]

References: [1]Bulletin de la Societe Chimique de France,1987,p. 438 - 440.

12
[ 123-54-6 ]
[ 5027-32-7 ]
[ 115241-30-0 ]

References: [1]Bulletin de la Societe Chimique de France,1987,p. 438 - 440.

13
[ 5027-32-7 ]
[ 106-49-0 ]
[ 112086-81-4 ]

References: [1]Russian Journal of General Chemistry,2001,vol. 71,p. 1497 - 1498.

14
[ 5027-32-7 ]
[ 64-04-0 ]
1-(2-phenylethyl)-3,4-diacetyl-2,5-dimethylpyrrole [ No CAS ]

References: [1]Russian Journal of General Chemistry,2001,vol. 71,p. 1497 - 1498.

15
[ 5027-32-7 ]
[ 106-40-1 ]
1-(4-bromophenyl)-3,4-diacetyl-2,5-dimethylpyrrole [ No CAS ]

References: [1]Russian Journal of General Chemistry,2001,vol. 71,p. 1497 - 1498.

16
[ 5027-32-7 ]
[ 4469-80-1 ]
1-[4-acetyl-2,5-dimethyl-1-(4-propoxy-phenyl)-1H-pyrrol-3-yl]-ethanone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1295 - 1298.

17
[ 5027-32-7 ]
[ 104-94-9 ]
[ 112086-82-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1295 - 1298.

18
[ 5027-32-7 ]
[ 94-70-2 ]
1-[4-acetyl-1-(2-ethoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1295 - 1298.

19
[ 5027-32-7 ]
[ 621-33-0 ]
1-[4-acetyl-1-(3-ethoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1295 - 1298.

20
[ 89943-11-3 ]
[ 5027-32-7 ]
1-[4-acetyl-1-(5-ethoxy-pyridin-2-yl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone [ No CAS ]