615-06-5|Methyl 2-Furoylacetate| Ambeed

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Quality Control of [ 615-06-5 ] Purity: 97% SDS Specification

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Product Details of [ 615-06-5 ]

CAS No. :	615-06-5
Formula :	C₈H₈O₄
M.W :	168.15
SMILES Code :	O=C(OC)CC(C1=CC=CO1)=O
MDL No. :	MFCD03424758
InChI Key :	YGTDKZHHEPVYGJ-UHFFFAOYSA-N
Pubchem ID :	228584

Safety of [ 615-06-5 ]

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

Computational Chemistry of [ 615-06-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	5
Fraction Csp3	0.25
Num. rotatable bonds	4
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	39.8
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	56.51 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.97
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	1.03
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.03
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.	-0.5
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	1.31
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.97

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.58
Solubility	4.47 mg/ml ; 0.0266 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.	-1.81
Solubility	2.62 mg/ml ; 0.0156 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	-2.03
Solubility	1.55 mg/ml ; 0.00925 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.	-6.59 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)	2.13

Application In Synthesis of [ 615-06-5 ]

* 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 [ 615-06-5 ]

[ 615-06-5 ] Synthesis Path-Downstream 1~35

1
[ 611-13-2 ]
[ 79-20-9 ]
[ 615-06-5 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 5857.
[2]Journal of Organic Chemistry,1951,vol. 16,p. 269,275.

2
[ 615-06-5 ]
3-[2]furyl-2-hydroxyimino-3-oxo-propionic acid methyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1951,vol. 16,p. 269,275.

3
[ 79-20-9 ]
[ 614-99-3 ]
[ 615-06-5 ]

References: [1]Journal of the American Chemical Society,1928,vol. 50,p. 1438,1439.

4
[ 98-01-1 ]
[ 6832-16-2 ]
[ 615-06-5 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1988,vol. 37,p. 722 - 727.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1988,p. 842 - 847.

5
[ 67-56-1 ]
[ 78078-05-4 ]
[ 615-06-5 ]

References: [1]Chemical and pharmaceutical bulletin,1988,vol. 36,p. 401 - 404.

6
[ 1192-62-7 ]
[ 616-38-6 ]
[ 615-06-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In toluene; mineral oil; for 5h;Reflux;	General procedure: To a solution of ketone (20 mmol) in toluene (80 mL) was added dimethyl carbonate (60 mmol) and NaH (40 mmol, 60%). The reaction mixture was refluxed for 5 h until TLC indicated the total consumption of the ketone. After cooling, the reaction mixture was poured into ice-water (100 mL), acidified with 3 M HCl to pH 2-3 and extracted with EtOAc (100 mL x3). The combined organic layer was dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (petroleum ether /EtOAc = 10/1) to afford the desired compound.

References: [1]Chemistry Letters,1999,p. 1055 - 1056.
[2]Heterocycles,2004,vol. 62,p. 375 - 386.
[3]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1783 - 1786.
[4]European Journal of Organic Chemistry,2014,vol. 2014,p. 3097 - 3100.
[5]Journal of the American Chemical Society,2011,vol. 133,p. 3300 - 3303.
[6]Chemical Communications,2012,vol. 48,p. 2340 - 2342.
[7]Tetrahedron Letters,2014,vol. 55,p. 6534 - 6537.
[8]Organic Letters,2014,vol. 16,p. 5410 - 5413.
[9]Angewandte Chemie - International Edition,2014,vol. 53,p. 12210 - 12213.
Angew. Chem.,2014,vol. 126,p. 12406 - 12409,4.
[10]Advanced Synthesis and Catalysis,2016,vol. 358,p. 2035 - 2040.
[11]Organic Letters,2017,vol. 19,p. 5130 - 5133.
[12]Synthesis,2016,vol. 48,p. 1359 - 1370.
[13]ChemMedChem,2018,vol. 13,p. 1744 - 1750.

7
[ 615-06-5 ]
[ 160237-44-5 ]
C₅₀H₆₀O₁₅Si [ No CAS ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 239 - 242.

8
[ 615-06-5 ]
[ 25290-21-5 ]
[ 252366-36-2 ]
3-hydroxy-3-(tetrahydro-furan-2-yl)-propionic acid methyl ester [ No CAS ]

References: [1]Heterocycles,2004,vol. 62,p. 375 - 386.
[2]Chemistry Letters,1999,p. 1055 - 1056.

9
[ 615-06-5 ]
(R)-3-Hydroxy-3-(tetrahydro-furan-2-yl)-propionic acid methyl ester [ No CAS ]
(S)-3-Hydroxy-3-(tetrahydro-furan-2-yl)-propionic acid methyl ester [ No CAS ]

References: [1]Chemistry Letters,1999,p. 1055 - 1056.

Yield	Reaction Conditions	Operation in experiment
		Example 39 Methyl 2-Furanoylacetate beta-ketoester: 20 equivalents, reaction time: 8 hours. Yield: 61 mg, recovery: 66%. The product is the ester compound represented by the following structural formula, and its 1H-NMR (500 MHz, CDCl3) is the same as that of the compound in Example 19.

11
[ 615-06-5 ]
[ 5396-64-5 ]
(4S,5S)-5-(3,4-Dimethoxy-phenyl)-4,5-dihydro-[2,2']bifuranyl-3,4-dicarboxylic acid dimethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 5049 - 5051.

12
[ 615-06-5 ]
[ 153396-63-5 ]
[ 573976-79-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1783 - 1786.

13
[ 615-06-5 ]
(R)-3-Hydroxy-3-(S)-tetrahydro-furan-2-yl-propionic acid methyl ester [ No CAS ]
(S)-3-Hydroxy-3-(S)-tetrahydro-furan-2-yl-propionic acid methyl ester [ No CAS ]
(R)-3-Hydroxy-3-(R)-tetrahydro-furan-2-yl-propionic acid methyl ester [ No CAS ]
(S)-3-Hydroxy-3-(R)-tetrahydro-furan-2-yl-propionic acid methyl ester [ No CAS ]

References: [1]Heterocycles,2004,vol. 62,p. 375 - 386.

14
[ 615-06-5 ]
[ 80789-74-8 ]
[ 854948-62-2 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 3680 - 3683.

15
[ 615-06-5 ]
[ 1199-28-6 ]
[ 1047643-55-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4376 - 4380.

16
[ 615-06-5 ]
(3-{4-[2-(2,4-dichloro-phenoxy)-ethylcarbamoyl]-5-furan-2-yl-isoxazol-3-yl}-phenyl)-acetic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5488 - 5492.

17
[ 615-06-5 ]
[ 927187-54-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5488 - 5492.

18
[ 615-06-5 ]
(R)-2-(2-Furan-2-yl-2-oxo-ethyl)-4-methyl-pentanoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1783 - 1786.

19
[ 615-06-5 ]
(R)-2-(Furan-2-carbonyl)-3-isobutyl-succinic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1783 - 1786.

20
[ 615-06-5 ]
(R)-2-(2-Furan-2-yl-2-oxo-ethyl)-4-methyl-pentanoic acid [(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1783 - 1786.

21
[ 615-06-5 ]
(4R,5S,6R)-4-(3,4-Dimethoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-benzofuran-5,6-dicarboxylic acid dimethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 5049 - 5051.

22
[ 1192-62-7 ]
isopentyl magnesium halide [ No CAS ]
[ 615-06-5 ]

References: [1]Chemical and pharmaceutical bulletin,1988,vol. 36,p. 401 - 404.

23
[ 615-06-5 ]
2-acetylamino-3-[2]furyl-3-oxo-propionic acid methyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1951,vol. 16,p. 269,275.
[2]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1931 - 1936.

24
[ 615-06-5 ]
methyl 3-hydroxy-3-(2-furanyl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid; triethylamine;[N-[(1S,2S)-2-(amino-kappaN)-1,2-diphenylethyl]-p-tolylsulphonamidato-kappaN]chloro[(eta6)-cumene]ruthenium(II); In dichloromethane; at 30℃;	[0204] In a 100 ml multi-necked flask equipped with a sparging stirrer, reflux condenser and thermometer, a formic acid/Et3N mixture (molar ratio 1:1, molar ratio 1.05:1 based on the substrate) is prepared by slowly adding HCOOH dropwise to Et3N by a dropping funnel within 5 min with stirring and ice-cooling. The appropriate keto compound is then added to this biphasic mixture (500-5000 eq. based on the catalyst), the homogeneous yellow solution is optionally admixed with solvent, and the entire mixture is degassed by passing through argon for 20 min. It is heated to the target temperature and the dark red catalyst solution is added all at once by syringe to the reaction mixture with vigorous stirring. The mixture is stirred under argon for the stated time. [0205] The mixture is diluted with water and CH2Cl2 and stirred for a further 10 min, and, after phase separation, the H2O phase is extracted 2× with CH2Cl2. The combined organic phases are washed with NaCl solution, dried over MgSO4 and filtered, and then the solvent is removed on a rotary evaporator. The crude product is either distilled and recrystallized, for example from hexane/petroleum ether or from hexane/dichloromethane, or used as a crude mixture in further reactions. The product is obtained in 90-100% yield.

References: [1]Patent: US2003/225274,2003,A1 .Location in patent: Page 11-12.

25
[ 88-14-2 ]
[ 16695-14-0 ]
[ 2414-98-4 ]
[ 615-06-5 ]

Yield	Reaction Conditions	Operation in experiment
2.93 g (17.4 mmol, 69.6%)	With hydrogenchloride; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol;	Example 141 Synthesis of Compound 141 In 100 mL of methanol, was dissolved 5.90 g (50.0 mmol) of monomethyl malonate, and the resulting solution was mixed with 2.86 g (25 mmol) of magnesium ethoxide followed by stirring at room temperature for 4 hours. The reaction solution was concentrated and the residue was dried under reduced pressure. In 100 mL of tetrahydrofuran, was dissolved 2.80 g (25 mmol) of 2-furancarboxylic acid and the resulting solution was mixed with 4.45 g (27.4 mmol) of carbonyldiimidazole, followed by stirring for 1 hour. The reaction solution was added to a dry magnesium salt and stirred at room temperature for 19 hours. The reaction solution was concentrated; the residue was mixed with 100 mL of 1.5 N hydrochloric acid, extracted with ethyl acetate, and washed with an aqueous sodium hydrogencarbonate solution and saturated sodium chloride water. The resultant was dried over sodium sulfate anhydride, filtered, and concentrated. The residue was distilled (0.06 mmHg, 69 to 75) to give 2.93 g (17.4 mmol, 69.6%) of methyl 2-furancarbonylacetate as an anhydrous liquid.

References: [1]Patent: US6215016,2001,B1 .

26
[ 615-06-5 ]
[ 88284-48-4 ]
C₁₄H₁₂O₄ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4960 - 4964.

27
[ 38330-80-2 ]
[ 2979-48-8 ]
[ 615-06-5 ]

References: [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4960 - 4964.

28
[ 615-06-5 ]
[ 106-96-7 ]
[ 1242162-72-6 ]

References: [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1163 - 1168.

29
[ 615-06-5 ]
[ 593-56-6 ]
methyl (Z)-3-(furan-2-yl)-3-(methoxyimino)propanoate [ No CAS ]
[ 1257649-01-6 ]

References: [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 7963 - 7967.
[2]Chemical Communications,2012,vol. 48,p. 3996 - 3998.

30
[ 615-06-5 ]
[ 1272565-20-4 ]