[ CAS No. 539-88-8 ] {[proInfo.proName]}

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2D 3D

Structure of 539-88-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 539-88-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 539-88-8 ]

SDS Specification

Alternatived Products of [ 539-88-8 ]

Product Details of [ 539-88-8 ]

CAS No. :	539-88-8	MDL No. :	MFCD00009209
Formula :	C₇H₁₂O₃	Boiling Point :	No data available
Linear Structure Formula :	CH₃COCH₂CH₂COOC₂H₅	InChI Key :	GMEONFUTDYJSNV-UHFFFAOYSA-N
M.W :	144.17	Pubchem ID :	10883
Synonyms :

Calculated chemistry of [ 539-88-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.71
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	37.25
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) :	-7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.29
Log Po/w (XLOGP3) :	0.07
Log Po/w (WLOGP) :	0.92
Log Po/w (MLOGP) :	0.64
Log Po/w (SILICOS-IT) :	1.13
Consensus Log Po/w :	0.81

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.45
Solubility :	51.4 mg/ml ; 0.356 mol/l
Class :	Very soluble
Log S (Ali) :	-0.53
Solubility :	42.1 mg/ml ; 0.292 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.48
Solubility :	4.74 mg/ml ; 0.0329 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.64

Safety of [ 539-88-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P305+P351+P338	UN#:
Hazard Statements:	H227-H302+H332-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 539-88-8 ]

* 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 [ 539-88-8 ]
Downstream synthetic route of [ 539-88-8 ]

[ 539-88-8 ] Synthesis Path-Upstream 1~2

1
[ 539-88-8 ]
[ 65202-58-6 ]

Reference： [1] Patent: EP3333157, 2018, A1,

2
[ 74877-08-0 ]
[ 539-88-8 ]
[ 74877-08-0 ]
[ 176707-77-0 ]

Reference： [1] Tetrahedron Asymmetry, 2007, vol. 18, # 11, p. 1330 - 1337

[ 539-88-8 ] Synthesis Path-Downstream 1~11

1
[ 917-64-6 ]
[ 539-88-8 ]
[ 3123-97-5 ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 2322,2324

2
methylmagnesium iodide [ No CAS ]
[ 539-88-8 ]
[ 3123-97-5 ]

Reference： [1]Journal of the Chemical Society,1904,vol. 85,p. 1693

3
methyl magnesium ⁽¹⁺⁾; bromide [ No CAS ]
[ 539-88-8 ]
[ 3123-97-5 ]

Reference： [1]Journal of the Chemical Society,1904,vol. 85,p. 1693

4
[ 41453-02-5 ]
[ 539-88-8 ]
[ 3123-97-5 ]
[ 71441-79-7 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 503 - 506

5
[ 539-88-8 ]
methyl magnesium halide [ No CAS ]
[ 3123-97-5 ]

Reference： [1]Journal of the Chemical Society,1904,vol. 85,p. 1693

6
[ 7768-28-7 ]
[ 539-88-8 ]
[ 722539-54-0 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2004,vol. 23,p. 89 - 115
[2]European Journal of Organic Chemistry,2006,p. 197 - 206
[3]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 939 - 942

7
[ 539-88-8 ]
[ 2882-15-7 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 638 - 648
[2],2019,vol. 10,p. 1935 - 1947

8
[ 539-88-8 ]
[ 3123-97-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	With phosphoric acid; methylmagnesium bromide; In diethyl ether; ethyl acetate; benzene;	EXAMPLE 1 5,5-Dimethyl-dihydrofuran-2-one (IV) A solution of ethyl levulinate (50.0 g, 0.345 mole) in anhydrous ethyl ether (200 mL) and anhydrous benzene (200 mL) was treated with methylmagnesium bromide (3.0M solution in diethyl ether, 121.0 mL, 0.365 mole) dropwise at 0° C. over 30 minutes. At this time the ether was removed by slow distillation and the resulting benzene solution was heated at reflux for 2 hours. An ice cold solution of 20percent phosphoric acid (500 mL) and ethyl acetate (500 mL) were then added at 0° C. The organic phase was then separated, washed with brine (1*300 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The resulting crude oil was purified by distillation (b.p., 43° C., 0.35 mm Hg) yielding 26.0 g of the title furan-2-one (Y: 66percent); 1 H-NMR (CDCl3): delta2.62 (t, J=8.5 Hz, 2H), 2.05 (t, J=8.5 Hz, 2H), 1.42 (s, 6H).
66%	With phosphoric acid; methylmagnesium bromide; In diethyl ether; ethyl acetate; benzene;	EXAMPLE 1 5,5-Dimethyl-dihydrofuran-2-one (IV) A solution of ethyl levulinate (50.0 g, 0.345 mole) in anhydrous ethyl ether (200 mL) and anhydrous benzene (200 mL) was treated with methylmagnesium bromide (3.0M solution in diethyl ether, 121.0 mL, 0.365 mole) dropwise at 0° C. over 30 minutes. At this time the ether was removed by slow distillation and the resulting benzene solution was heated at reflux for 2 hours. An ice cold solution of 20percent phosphoric acid (500 mL) and ethyl acetate (500 mL) were then added at 0° C. The organic phase was then separated, washed with brine (1*300 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The resulting crude oil was purified by distillation (b.p., 43° C., 0.35 mm Hg) yielding 26.0 g of the title furan-2-one (Y: 66percent); 1 H-NMR (CDCl3): delta 2.62 (t, J=8.5 Hz, 2H), 2.05 (t, J=8.5 Hz, 2H), 1.42 (s, 6H).

Reference： [1]Patent: US5618839,1997,A
[2]Patent: US5648385,1997,A

9
aqueous potassium hydroxide [ No CAS ]
[ 539-88-8 ]
[ 3123-97-5 ]

Yield	Reaction Conditions	Operation in experiment
49%	With sulfuric acid; In methyl magnesium iodide; water;	EXAMPLE 38 STR47 4,5-Dihydro-5,5-dimethyl-2(3H)-furanone A solution of ethyl levulinate (130.2 g, 0.9 mole) in 400 ml ether and 500 ml benzene was cooled in an ice bath and treated with the slow addition of methylmagnesium iodide (1 mole in 500 ml ether). The ether was removed by distillation, and the remaining solution was refluxed for 3 hours. After cooling the reaction mixture was quenched with 1N sulfuric acid. The aqueous phase was washed with diethyl ether, and then the combined organic solutions were treated with aqueous potassium hydroxide (40 g in 200 ml water) and stirred for 1 hour. The aqueous layer was acidified with 50percent sulfuric acid and extracted with ether. The ether layer was dried over sodium sulfate, filtered and evaporated to a brown syrup, which was distilled to give the title compound (50 g, 49percent).

Reference： [1]Patent: US5071853,1991,A

10
[ 75-16-1 ]
[ 539-88-8 ]
[ 3123-97-5 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; benzene; at 0℃; for 5h;Heating / reflux;	Ethyl Levulinate (5Og) was dissolved in 500 ml of diethylether/benzene (1/1 v/v), cooled to O0C and a MeMgBr solution (127ml, 3M in diethylether) was added drop wise over 2 h. The ether was evaporated and the resulting benzene solution heated to a gentle reflux for 3 h. Removed benzene and redissolved in EtOAc, washed with IN H2SO4, H2O and cone. NaHCO3. Dried over MgSO4, filtered and concentrated to give 5,5-Dimethyl- dihydro-furan-2-one.

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 8615 - 8618
[2]Journal of Natural Products,2012,vol. 75,p. 1765 - 1776
[3]Patent: WO2007/48070,2007,A2 .Location in patent: Page/Page column 108

11
[ 539-88-8 ]
[ 65202-58-6 ]

Reference： [1]Patent: EP3333157,2018,A1

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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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[ 539-88-8 ]

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Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
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Code	Phrase
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P302 + P352	IF ON SKIN: wash with plenty of soap and water.
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P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
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P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H373	May cause damage to organs through prolonged or repeated exposure
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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
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 539-88-8 ] {[proInfo.proName]}

Quality Control of [ 539-88-8 ]

Related Doc. of [ 539-88-8 ]

Product Details of [ 539-88-8 ]

Calculated chemistry of [ 539-88-8 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 539-88-8 ]

Application In Synthesis of [ 539-88-8 ]

[ 539-88-8 ] Synthesis Path-Upstream 1~2

[ 539-88-8 ] Synthesis Path-Downstream 1~11

Technical Information

Related Functional Groups of [ 539-88-8 ]

Aliphatic Chain Hydrocarbons

Esters

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 539-88-8 ]