[ CAS No. 3249-68-1 ] {[proInfo.proName]}

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2D 3D

Structure of 3249-68-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 3249-68-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3249-68-1 ]

SDS Specification

Alternatived Products of [ 3249-68-1 ]

Product Details of [ 3249-68-1 ]

CAS No. :	3249-68-1	MDL No. :	MFCD00009401
Formula :	C₈H₁₄O₃	Boiling Point :	No data available
Linear Structure Formula :	C₃H₇C(O)CH₂C(O)OC₂H₅	InChI Key :	KQWWVLVLVYYYDT-UHFFFAOYSA-N
M.W :	158.20	Pubchem ID :	238498
Synonyms :		Chemical Name :	Ethyl Butyrylacetate

Calculated chemistry of [ 3249-68-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	6
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.05
TPSA :	43.37 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.74
Log Po/w (XLOGP3) :	1.08
Log Po/w (WLOGP) :	1.31
Log Po/w (MLOGP) :	0.97
Log Po/w (SILICOS-IT) :	1.55
Consensus Log Po/w :	1.33

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.11
Solubility :	12.4 mg/ml ; 0.0785 mol/l
Class :	Very soluble
Log S (Ali) :	-1.58
Solubility :	4.14 mg/ml ; 0.0261 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.9
Solubility :	2.0 mg/ml ; 0.0126 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.82

Safety of [ 3249-68-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P210-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P370+P378-P403+P235-P501	UN#:
Hazard Statements:	H227-H302+H312+H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3249-68-1 ]

* 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.

Upstream synthesis route of [ 3249-68-1 ]
Downstream synthetic route of [ 3249-68-1 ]

[ 3249-68-1 ] Synthesis Path-Upstream 1~1

1
[ 3249-68-1 ]
[ 50461-74-0 ]

Reference： [1] Journal of Organic Chemistry, 2013, vol. 78, # 14, p. 7268 - 7273

[ 3249-68-1 ] Synthesis Path-Downstream 1~5

1
[ 6414-69-3 ]
[ 3249-68-1 ]
[ 858795-64-9 ]

Reference： [1]Monatshefte fur Chemie,1936,vol. 69,p. 190

2
[ 1450-93-7 ]
[ 3249-68-1 ]
[ 106263-63-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 245 - 247

3
[ 3249-68-1 ]
[ 6099-90-7 ]
[ 66346-59-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In ethyl acetate;	EXAMPLE 1 5,7-Dihydroxy-4-propylcoumarin5 (2) Concentrated sulfuric acid (200 mL) was added into a mixture of <strong>[6099-90-7]phloroglucinol dihydrate</strong> (150 g, 0.926 mol) and ethyl butyrylacetate (161 g, 1.02 mol). The resulting mixture was stirred at 90 C. for two hours whereupon it was poured onto ice. The solid product was collected by filtration, and then dissolved in ethyl acetate. The solution was washed with brine and dried over Na2 SO4. After removal of the solvent in vacuo, the residue was triturated with hexane to provide essentially pure compound 2 (203 g) in quantitative yield, mp 233-235 C. (Lit.5 236-238 C.). 1 H-NMR5 (DMSO-d6) delta 0.95 (3H,t,J=6.9 Hz, CH3); 1.63 (2H, apparent sextet, J=7.0 Hz, CH2); 2.89 (2H,t,J=7.5 Hz, CH2); 5.85 (1H, s, H3); 6.22 (1H, d, J=2.0 Hz, H6); 6.31 (1H, d, J=2.0 Hz, H8); 10.27 (1H, s, OH); 10.58 (1H, s, OH); MS (EI); 220(100, M+); 205 (37.9, M-CH3); 192 (65.8, M-C2 H4); 177 (24.8, M-C3 H7); 164 (60.9, M-CHCO2 +1); 163 (59.6 M-CHCO2); IR (KBr): 3210 (vs and broad, OH); 1649 (vs, sh); 1617 (vs, sh); 1554 (s) cm-1; Anal. calcd. for C12 H24 O4: C, 65.45; H, 5.49; Found: C, 65.61; H, 5.44.
	With sulfuric acid; In ethyl acetate;	EXAMPLE 1 5,7-Dihydroxy-4-propylcoumarin5 (2) Concentrated sulfuric acid (200 mL) was added into a mixture of <strong>[6099-90-7]phloroglucinol dihydrate</strong> (150 g, 0.926 mol) and ethyl butyrylacetate (161 g, 1.02 mol). The resulting mixture was stirred at 90 C. for two hours whereupon it was poured onto ice. The solid product was collected by filtration, and then dissolved in ethyl acetate. The solution was washed with brine and dried over Na2 SO4. After removal of the solvent in vacuo, the residue was triturated with hexane to provide essentially pure compound 2 (203 g) in quantitative yield, mp 233-235 C. (Lit.5 236-238 C.). 1 H-NMR5 (DMSO-d6) delta0.95 (3H,t,J=6.9 Hz, CH3); 1.63 (2H, apparent sextet, J=7.0 Hz, CH2); 2.89 (2H,t,J=7.5Hz,CH2); 5.85 (1H, s, H3); 6.22 (1H, d, J=2.0 Hz, H6); 6.31 (1H, d, J=2.0 Hz, H8); 10.27 (1H, s, OH); 10.58 (1H, s, OH); MS (EI); 220(100, M+); 205 (37.9, M-CH3); 192 (65.8, M-C2 H4); 177 (24.8, M-C3 H7); 164 (60.9, M-CHCO2 +1); 163 (59.6 M-CHCO2); IR (KBr): 3210 (vs and broad, OH); 1649 (vs, sh); 1617 (vs, sh); 1554 (s) cm-1; Anal. calcd. for C12 H24 O4: C, 65.45; H, 5.49; Found: C, 65.61; H, 5.44.
	With sulfuric acid; In ethyl acetate;	EXAMPLE 1 5,7-Dihydroxy-4-propylcoumarin5 (2) Concentrated sulfuric acid (200 mL) was added into a mixture of <strong>[6099-90-7]phloroglucinol dihydrate</strong> (150 g, 0.926 mol) and ethyl butyrylacetate (161 g, 1.02 mol). The resulting mixture was stirred at 90C for two hours whereupon it was poured onto ice. The solid product was collected by filtration, and then dissolved in ethyl acetate. The solution was washed with brine and dried over Na2 SO4. After removal of the solvent in vacuo, the residue was triturated with hexane to provide essentially pure compound 2 (203 g) in quantitative yield, mp 233-235 C. (Lit.5 236-238 C.). 1 H-NMR5 (DMSO-d6) delta 0.95 (3H,t,J=6.9 Hz, CH3); 1.63 (2H, apparent hextet, J=7.0 Hz, CH2); 2.89 (2H,t,J=7.5 Hz,CH2); 5.85 (1H, s, H3); 6.22 (1H, d, J=2.0 Hz, H6); 6.31 (1H, d, J=2.0 Hz, H8); 10.27 (1H, s, OH); 10.58 (1H, s, OH); MS (EI); 220(100, M+); 205 (37.9, M--CH3); 192 (65.8, M--C2 H4); 177 (24.8, M--C3 H7); 164 (60.9, M--CHCO2 +1); 163 (59.6 M--CHCO2); IR (KBr): 3210 (vs and broad, OH); 1649 (vs, sh); 1617 (vs, sh); 1554 (s) cm-1); Anal. calcd. for C12 H24 O4: C, 65.45; H, 5.49; Found: C, 65.61; H, 5.44.

	In ethyl acetate;	EXAMPLE 1 5,7-Dihydroxy-4-propylcoumarin55 (2) Concentrated sulfric acid (200 mL) was added into a mixture of <strong>[6099-90-7]phloroglucinol dihydrate</strong> (150 g, 0.926 mol) and ethyl butyrylacetate (161 g, 1.02 mol). The resulting mixture was stirred at 90 C. for two hours whereupon it was poured onto ice. The solid product was collected by filtration, and then dissolved in ethyl acetate. The solution was washed with brine and dried over Na2SO4. After removal of the solvent in vacuo, the residue was triturated with hexane to provide essentially pure compound 2 (203 g) in quantitative yield, mp 233-235 C. (Lit.55 236-238 C.). 1H-NMR55 (DMSO-6) delta0.95 (3H, t, J=6.9 Hz, CH3); 1.63 (2H, apparent sextet, J=7.0 Hz, CH2); 2.89 (2H, t, J=7.5Hz,CH2); 5.85 (1H, s, H3); 6.22 (1H, d, J=2.0 Hz, H6); 6.31 (1H, d, J=2.0 Hz, H8); 10.27 (1H, s, OH); 10.58 (1H, s, OH); MS (EI); 220(100, M+); 205 (37.9, M-CH3); 192 (65.8, M-C2H4); 177 (24.8, M-C3H7); 164 (60.9, M-CHCO2+1); 163 (59.6 M-CHCO2); IR (KBr): 3210 (vs and broad, OH); 1649 (vs, sh); 1617 (vs, sh); 1554 (s) cm-1; Anal. calcd. for C12H24O4: C, 65.45; H, 5.49;.Found: C, 65.61; H, 5.44.
	With sulfuric acid; In ethyl acetate;	EXAMPLE 1 5,7-Dihydroxy4-propylcoumarin5 (2) Concentrated sulfuric acid (200 mL) was added into a mixture of <strong>[6099-90-7]phloroglucinol dihydrate</strong> (150 g, 0.926 mol) and ethyl butyrylacetate (161 g, 1.02 mol). The resulting mixture was stirred at 90 C. for two hours whereupon it was poured onto ice. The solid product was collected by filtration, and then dissolved in ethyl acetate. The solution was washed with brine and dried over Na2SO4. After removal of the solvent in vacuo, the residue was triturated with hexane to provide essentially pure compound 2 (203 g) in quantitative yield, mp 233-235 C. (Lit.5 236-238 C.). 1H-NMR5 (DMSO-d6) delta0.95 (3H, t, J=6.9 Hz, CH3); 1.63 (2H, apparent sextet, J=7.0 Hz, CH2); 2.89 (2H, t, J=7.5Hz, CH2); 5.85 (1H, s, H3); 6.22 (1H, d, J=2.0 Hz, H6); 6.31 (1H, d, J=2.0 Hz, H8); 10.27 (1H, s, OH); 10.58 (1H, s, OH); MS (EI); 220(100, M+); 205 (37.9, M-1055 CH3); 192 (65.8, M-C2H4); 177 (24.8, M-C3H7); 164 (60.9, M-CHCO2+1); 163 (59.6 M-CHCO2); IR (KBr): 3210 (vs and broad, OH); 1649 (vs, sh); 1617 (vs, sh); 1554 (s) cm-1; Anal. calcd. for C12H24O4: C, 65.45; H, 5.49; Found: C, 65.61; H, 5.44.

Reference： [1]Patent: US5892060,1999,A
[2]Patent: US5977385,1999,A
[3]Patent: US6043271,2000,A
[4]Patent: US6268393,2001,B1
[5]Patent: US6277879,2001,B1

4
[ 3249-68-1 ]
[ 2293-07-4 ]
[ 929561-70-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example B20Preparation of Compound 102; Sulfuryl chloride (0.0055 mol) was added dropwise to a solution of 3-oxo-hexanoic acid, ethyl ester (0.0055 mol) in CH2Cl2 (q.s.). The reaction mixture was stirred for 2 hours at room temperature. The solvent was evaporated. A solution of (4-methoxyphenyl)-thiourea (0.0055 mol) in EtOH (100 ml) was added to the residue. The resultant reaction mixture was stirred and refluxed for 4 hours. A saturated aqueous NaHCO3 solution was added. This mixture was extracted with EtOAc. The separated organic layer was purified by column chromatography over silica gel. The product fractions were collected and the solvent was evaporated, yielding compound 102.

Reference： [1]Patent: US2011/269748,2011,A1 .Location in patent: Page/Page column 42

5
[ 3249-68-1 ]
[ 50461-74-0 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 7268 - 7273

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Isomers

Technical Information

? Acyl Group Substitution ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bouveault-Blanc Reduction ? Bucherer-Bergs Reaction ? Catalytic Hydrogenation ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Ester Cleavage ? Fischer Indole Synthesis ? Grignard Reaction ? Heat of Combustion ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 3249-68-1 ] {[proInfo.proName]}

Quality Control of [ 3249-68-1 ]

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Calculated chemistry of [ 3249-68-1 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 3249-68-1 ]

[ 3249-68-1 ] Synthesis Path-Upstream 1~1

[ 3249-68-1 ] Synthesis Path-Downstream 1~5

Technical Information

Related Functional Groups of [ 3249-68-1 ]

Aliphatic Chain Hydrocarbons

Esters

Ketones

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[ 3249-68-1 ]