3883-58-7|2,2-Dimethyl-1,3-cyclopentanedione| Ambeed

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Quality Control of [ 3883-58-7 ] Purity: 97% SDS Specification

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Product Details of [ 3883-58-7 ]

CAS No. :	3883-58-7
Formula :	C₇H₁₀O₂
M.W :	126.15
SMILES Code :	O=C1C(C)(C)C(CC1)=O
MDL No. :	MFCD00074900
InChI Key :	VXVZVJNSRQRUTI-UHFFFAOYSA-N
Pubchem ID :	19763

Safety of [ 3883-58-7 ]

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

Computational Chemistry of [ 3883-58-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	0
Fraction Csp3	0.71
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	33.79
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	34.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.36
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	0.55
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.94
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.	0.31
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	1.92
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.02

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.97
Solubility	13.6 mg/ml ; 0.107 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.	-0.84
Solubility	18.3 mg/ml ; 0.145 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	-1.77
Solubility	2.16 mg/ml ; 0.0171 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.	-6.68 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)	1.36

Application In Synthesis of [ 3883-58-7 ]

* 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 [ 3883-58-7 ]

[ 3883-58-7 ] Synthesis Path-Downstream 1~35

1
[ 5815-08-7 ]
[ 3883-58-7 ]
4,4-Dimethyl-3,5-dioxo-cyclopentane-1,2-dicarbaldehyde [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1972,vol. 762,p. 62 - 72.

2
[ 5815-08-7 ]
[ 3883-58-7 ]
4,5-Bis-[1-dimethylamino-meth-(E)-ylidene]-2,2-dimethyl-cyclopentane-1,3-dione [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1972,vol. 762,p. 62 - 72.

3
[ 765-69-5 ]
[ 77-78-1 ]
[ 3883-58-7 ]

References: [1]Justus Liebigs Annalen der Chemie,1972,vol. 762,p. 62 - 72.

4
[ 765-69-5 ]
[ 74-88-4 ]
[ 3883-58-7 ]

Yield	Reaction Conditions	Operation in experiment
93%		The published procedure was followed. (Agosta, W. C.; Smith, A. B. J. Org. Chem. 1970, 35, 3856) A mixture of 2-methyl-1,3-cyclopentanedione (10.025 g, 89.4 mmol, Aldrich), methyl iodide (6.0 mL, 96.4 mmol, Aldrich), and KOH (5.097 g, 90.8 mmol) in H2O (25 mL)/dioxane (75 mL) was heated at reflux. After 5 h, a solution of KOH (2 g) and MeI (2.4 mL) in H2O (5 mL)/dioxane (15 mL) was added and after another 3 h at reflux the solution was allowed to stir at room temperature overnight. In the morning, the reaction was continued by addition of a solution of KOH (2 g) and MeI (2.4 mL) in H2O (5 mL)/dioxane (15 mL) and heating at reflux. After 4 h, the mixture was allowed to cool to room temperature and was extracted with ether (1?100 mL, 3?75 mL). The combined ether extracts were evaporated, the residue combined with HCl (50 mL 10percent), and the resulting mixture was placed in a 120 C. oil bath until boiling was observed (ca. 15 min.). The mixture was then allowed to cool to room temperature, was neutralized by addition of NaHCO3 solution (150 mL, saturated) and the resulting mixture then extracted with CH2Cl2 (4?75 mL). The combined CH2Cl2 solution was dried (MgSO4), filtered and evaporated to leave a brown oil (10.474 g, 83 mmol, 93percent) which was used directly in the next step.
93%	With potassium hydroxide; In 1,4-dioxane; water; at 20℃;Reflux;	Synthesized according to Agosta and Smith, J. Org. Chem., 35: 3856 (1970). A mixture of 2-methyl-1,3-cyclopentanedione (10.025 g, 89.4 mmol, Aldrich), methyl iodide (6.0 mL, 96.4 mmol, Aldrich), and KOH (5.097 g, 90.8 mmol) in water (25 mL)/dioxane (75 mL) was heated at reflux. After 5 hours, a solution of KOH (2 g) and Mel (2.4 mL) in water (5 mL)/dioxane (15 mL) was added and after another 3 hours at reflux, the solution was stirred at room temperature overnight. A solution of KOH (2 g) and Mel (2.4 mL) in water (5 mL)/dioxane (15 mL) was added to the overnight reaction and heating at reflux. After 4 hours, the mixture was cooled to room temperature and extracted with ether (1×100 mL, 3×75 mL). The combined ether extracts were evaporated, the residue combined with 10percent HCl (50 mL), and the resulting mixture placed in a 120° C. oil bath until it began boiling (ca. 15 minutes). The mixture was cooled to room temperature, neutralized by addition of saturated NaHCO3 solution (150 mL) and the resulting mixture extracted with CH2Cl2 (4×75 mL). The combined CH2Cl2 solution was dried (MgSO4), filtered and evaporated to leave a brown oil (10.474 g, 83 mmol, 93percent) which was used directly in the next step.
36%		2-Methyl-1,3-cyclopentanodione (7) (1 eq, 351 mmol, 39.4 g) was added to a solution of NaOH (1 eq, 351 mmol, 14.1 g) in water (75 mL) at 0 °C. After stirring for 15 min, the solution was evaporated under reduced pressure to dryness. Sodium salt of 7 was obtained with quantitative yield. To a suspension of sodium salt of 7 (47.4 g) in DMF (300 mL), MeI (1.5 eq, 526.5 mmol, 33.0 mL) was added and resulting mixture was stirred vigoriously overnight. Then, the reaction mixture was poured into water (2 L) and extracted with CHCl3 (4x100 mL). The combined extracts were washed with water (5x150 mL) and brine (200 mL), dried over anh. MgSO4 and concentrated under reduced pressure to yield dark oil (35.7 g). The oil was dissolved in 12percent HCl (330 mL) and refluxed for 1 h. The reaction mixture was cooled to rt, neutralized (to pH = 7) with 20percent aq. NaOH. Then, sat. aq. solution of Na2CO3 (100 mL) was added and the product was extracted with CHCl3 (4x100 mL). The combined extracts were washed with brine (100 mL), dried over anh. MgSO4 and evaporated under reduced pressure to afford 8 (15.79 g, 36percent). Physical state: pale brown solid.; IR (neat, cm-1): 2980, 1719, 1459, 1286, 993.; 1H NMR (400 MHz, CDCl3), delta (ppm): 2.80 (s, 4H), 1.15 (s, 6H).

With potassium hydroxide; In 1,4-dioxane; water; for 11h;Reflux;

A mixture of 2-methylcyclopentane-l,3-dione (49.98 g, 446 mmol), potassium hydroxide (25.5 g, 455 mmol) and iodomethane (30.1 mL, 481 mmol) in dioxane (390 mL) and water (130 mL) was heated to reflux for 5 h. A biphasic mixture of potassium hydroxide (10.4 g), iodomethane (12.5 mL), water (26 mL) and dioxane (78 mL) was added. The mixture was heated at reflux for 3 additional hours and then stirred at ambient temperature overnight. Another portion of a biphasic mixture of potassium hydroxide (10.4 g), iodomethane (12.5 mL), water (26 mL) and dioxane (78 mL) was added. The mixture was heated at reflux for 3 h, cooled to room temperature and extracted with ether (600 mL, then 2x400 mL). The combined extracts were concentrated using a rotavap while keeping the bath temperature at or below room temperature to prevent loss of volatile product. The residue was treated with 10percent hydrochloric acid (250 mL) and placed in a 120 °C oil bath until it started to boil (~15 min). The mixture was cooled with an ice-water bath, diluted with water (250 mL) and treated with careful addition of sodium carbonate until carbon dioxide release stopped. The pH of the solution was 8-9. The mixture was extracted with dichloromethane (4x200 mL). The combined extracts were dried (MgS04), filtered and concentrated while keeping water bath at or below room temperature. The residue was further dried under vacuum briefly to remove residual solvent to give 2,2- dimethylcyclopentane-l,3-dione as tan solid (38.1 g, 68percent yield). XH NMR (400 MHz, chloroform-if) delta ppm 2.81 (4 H, s), 1.16 (6 H, s); LC retention time: 0.990 (analytical HPLC Method F).

References: [1]Patent: US2004/157901,2004,A1 .Location in patent: Page 10.
[2]Patent: US9334262,2016,B2 .Location in patent: Page/Page column 62.
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 5721 - 5726.
[4]Advanced Synthesis and Catalysis,2016,vol. 358,p. 1392 - 1397.
[5]Organic Letters,2000,vol. 2,p. 933 - 936.
[6]Journal of Organic Chemistry,1982,vol. 47,p. 4491 - 4498.
[7]Tetrahedron Letters,2017,vol. 58,p. 4285 - 4288.
[8]Tetrahedron Letters,1996,vol. 37,p. 7119 - 7122.
[9]Organic Letters,2016,vol. 18,p. 4836 - 4839.
[10]Journal of the Chemical Society. Perkin transactions I,1970,vol. 1,p. 10 - 18.
[11]Patent: WO2012/125886,2012,A1 .Location in patent: Page/Page column 107; 108.
[12]Organic Letters,2013,vol. 15,p. 4485 - 4487.

5
[ 765-69-5 ]
[ 676-88-0 ]
[ 3883-56-5 ]
[ 3883-58-7 ]

References: [1]Journal of Organic Chemistry,1983,vol. 48,p. 1362 - 1364.

6
[ 3142-58-3 ]
[ 3883-58-7 ]

References: [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 262 - 267.

7
[ 767-55-5 ]
[ 17082-61-0 ]
[ 3883-58-7 ]

References: [1]Canadian Journal of Chemistry,1990,vol. 68,p. 804 - 811.

8
[ 64-17-5 ]
[ 3883-58-7 ]
[ 54857-48-6 ]

References: [1]Tetrahedron Letters,1982,vol. 23,p. 481 - 484.
[2]Tetrahedron Letters,1982,vol. 23,p. 481 - 484.

9
[ 3883-58-7 ]
[ 16733-97-4 ]
[ 147428-75-9 ]
[ 147428-76-0 ]

References: [1]Journal of the American Chemical Society,1993,vol. 115,p. 1744 - 1753.

10
[ 3883-58-7 ]
[ 82102-52-1 ]

References: [1]Tetrahedron,1998,vol. 54,p. 6553 - 6564.
[2]Tetrahedron Letters,1982,vol. 23,p. 481 - 484.
[3]Tetrahedron Letters,1982,vol. 23,p. 481 - 484.

11
[ 3883-58-7 ]
[ 26154-26-7 ]
[ 26154-22-3 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 4491 - 4498.
[2]Tetrahedron Letters,1996,vol. 37,p. 7119 - 7122.

12
[ 3883-58-7 ]
[ 26154-22-3 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 7119 - 7122.
[2]Tetrahedron Letters,1985,vol. 26,p. 2181 - 2182.
[3]Russian Journal of Organic Chemistry,1996,vol. 32,p. 1317 - 1318.
[4]Organic Letters,2016,vol. 18,p. 4836 - 4839.
[5]Journal of Organic Chemistry,1970,vol. 35,p. 3856 - 3860.

13
[ 3883-58-7 ]
[ 76439-01-5 ]
[ 326796-87-6 ]

References: [1]Journal of the American Chemical Society,1981,vol. 103,p. 295 - 301.
[2]Tetrahedron Asymmetry,2000,vol. 11,p. 3883 - 3886.
[3]Journal of the American Chemical Society,2019.

14
[ 57613-21-5 ]
[ 3883-58-7 ]

References: [1]Synthesis,1986,p. 845 - 847.

15
[ 17082-61-0 ]
[ 77-76-9 ]
[ 3883-58-7 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 7119 - 7122.
[2]Tetrahedron Letters,1985,vol. 26,p. 2181 - 2182.

16
[ 17082-61-0 ]
[ 67-64-1 ]
[ 3883-58-7 ]

References: [1]Journal of Organic Chemistry,1994,vol. 59,p. 1485 - 1491.

17
[ 3883-58-7 ]
[ 67-64-1 ]
[ 82102-52-1 ]
[ 82102-53-2 ]

References: [1]Tetrahedron Letters,1982,vol. 23,p. 481 - 484.
[2]Tetrahedron Letters,1982,vol. 23,p. 481 - 484.

18
[ 765-69-5 ]
[ 74-88-4 ]
[ 3883-56-5 ]
[ 3883-58-7 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 4491 - 4498.
[2]Tetrahedron,1982,vol. 38,p. 1279 - 1283.
[3]Tetrahedron,1982,vol. 38,p. 1279 - 1283.

19
[ 5870-63-3 ]
[ 74-88-4 ]
[ 3883-58-7 ]

References: [1]Journal of Organic Chemistry,1970,vol. 35,p. 3856 - 3860.

20
[ 3883-58-7 ]
[ 1779-49-3 ]
2,2-Dimethyl-3-methylencyclopentanon [ No CAS ]

References: [1]Liebigs Annales,1995,p. 1061 - 1118.

21
[ 695-30-7 ]
[ 17082-61-0 ]
[ 3883-58-7 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 7119 - 7122.

22
[ 3883-58-7 ]
[ 76439-01-5 ]

Yield	Reaction Conditions	Operation in experiment
33%	With baker's yeast; In water; at 35℃; for 50h;	The published procedure was followed. (Brooks, D. W.; Hormoz, M.; Grothaus, P. G. J. Org. Chem. 1987, 52, 3223) A 35 C. (internal temperature) solution of D-glucose (106.73 g, 592 mmol, Aldrich) in H2O (690 mL) in a 4 L Erlenmeyer was treated with baker's yeast (71.065 g, Fleischmann's). The mixture was allowed to ferment for 2 h, then <strong>[3883-58-7]2,2-dimethyl-cyclopentane-1,3-dione</strong> (2) (7.316 g, 58 mmol) was added. [0108] The mixture was stirred for 48 h and then filtered through celite, washing with about 1 L CH2Cl2. The filtration was difficult due to the thick consistency of the yeast and it helped to continually add CH2Cl2 to the mixture and scrape the top of the celite layer with a spatula. The filtrate was transferred to a separatory funnel, and 100 mL brine was added and the layers were separated. Brine (400 mL) was added to the aqueous layer and the resulting solution extracted further with CH2Cl2 (3?500 mL). The combined CH2Cl2 solution was dried (MgSO4), filtered and evaporated to leave a yellow oil. Flash chromatography (11?5 cm, 20percent EtOAc/hexs>25percent>30percent>40percent>50percent) gave alcohol 3 (2.435 g, 19 mmol, 33percent).
33%	With D-glucose; In water; at 30℃; for 48h;Enzymatic reaction;	Synthesized according to Brooks, et al., J. Org. Chem., 52: 3223 (1987). A 35° C. (internal temperature) solution of D-glucose (106.73 g, 592 mmol, Aldrich) in water (690 mL) in a 4 L Erlenmeyer was treated with baker's yeast (71.065 g, Fleischmann's). The mixture was fermented for 2 hours, and <strong>[3883-58-7]2,2-dimethyl-cyclopentane-1,3-dione</strong> (2) (7.316 g, 58 mmol) was added. The mixture was stirred for 48 hours and filtered through celite, washing with about 1 L CH2Cl2. About 100 mL of brine was added to the filtrate and the layers separated using a separatory funnel. Brine (400 mL) was added to the aqueous layer and the resulting solution extracted further with CH2Cl2 (3×500 mL). The combined CH2Cl2 solution was dried (MgSO4), filtered and evaporated to leave a yellow oil. Flash chromatography (11×5 cm, 20percent EtOAc/hexs?25percent?30percent?40percent?50percent) gave alcohol 3 (2.435 g, 19 mmol, 33percent). (0210) The enantiomeric excess of 3 was assayed by 1H NMR of the corresponding Mosher's ester which was prepared by treatment of alcohol 3 (11 mg, 0.09 mmol) in dichloroethane (0.3 mL, Aldrich) with pyridine (27 muL, 0.33 mmol, Aldrich) and (R)-alpha-methoxy-alpha-trifluoromethylphenylacetic acid chloride (58 muL, 0.31 mmol, Fluka). The mixture was stirred overnight and then partitioned between water (10 mL) and ether (10 mL). The ether layer was washed with 1 M HCl (10 mL) and saturated NaHCO3 solution and then dried (MgSO4), filtered and evaporated. 1H NMR analysis was done on the crude ester.

References: [1]Tetrahedron Letters,1996,vol. 37,p. 7119 - 7122.
[2]Advanced Synthesis and Catalysis,2016,vol. 358,p. 1392 - 1397.
[3]Patent: US2004/157901,2004,A1 .Location in patent: Page 10.
[4]Patent: US9334262,2016,B2 .Location in patent: Page/Page column 62-63.
[5]Organic Letters,2012,vol. 14,p. 6354 - 6357.

23
[ 2916-31-6 ]
[ 17082-61-0 ]
[ 3883-58-7 ]

References: [1]Tetrahedron,1998,vol. 54,p. 6553 - 6564.

26
[ 3883-58-7 ]
[ 266341-08-6 ]