(R)-(+)-3-methyl-4-methoxymethyloxybutanenitrile
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With sulfuric acid In acetic acid for 1.5h; Heating; | 93% |
A
(S)-3-methyl-4-butanolide
B
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With lithium borohydride In tetrahydrofuran at 50℃; for 1h; | A 69% B n/a |
methyl (S)-(+)-3-methyl-5-oxohexanoate
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Stage #1: methyl (S)-(+)-3-methyl-5-oxohexanoate With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 48h; Baeyer-Villager oxidation; Stage #2: With potassium hydroxide In methanol for 4h; Heating; Stage #3: With hydrogenchloride pH=3 - 4; | 68% |
(3R)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyronitrile
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With sulfuric acid In acetic acid Heating; | 60% |
(S)-3-Methyl-4-<(tetrahydropyranyl)oxy>butanenitrile
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 7h; Heating; | 46% |
Multi-step reaction with 2 steps 1: aq. HCl / methanol / 4 h / Heating 2: 32.0 g / aq. NaOH / 5 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: aq. KOH / ethane-1,2-diol / 6 h / Heating 2: aq. HCl / 0.25 h / 100 °C View Scheme |
(R)-4-(iodomethyl)dihydrofuran-2(3H)-one
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With hydrogen; calcium carbonate; Raney Ni W-7 In ethanol for 0.5h; Ambient temperature; | 8.8% |
methyl (R)-3-hydroxy-2-methylpropionate
(R)-3-methyl-γ-butyrolactone
(R)-3-Methyl-4-[((E)-propenyl)oxy]-butyraldehyde
A
(S)-3-methyl-4-butanolide
B
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Jones oxidation; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(R)-(+)-4-tert. butoxy-3-methylbutyric acid
A
(S)-3-methyl-4-butanolide
B
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 1.5h; Heating; Yield given. Title compound not separated from byproducts; |
trans-(R)-2-Octen-4-ol
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Multistep reaction; |
(R)-4-Hydroxy-3-methyl-N-((R)-1-phenyl-ethyl)-butyramide
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With hydrogenchloride; potassium hydroxide Multistep reaction; |
A
(S)-3-methyl-4-butanolide
B
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
In tetrahydrofuran at -100℃; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(R)-4-Hydroxy-3-methyl-butyric acid
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 0.25h; Yield given; |
(-)-ethyl (R)-(E)-3,6-dimethyl-4-heptenoate
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With sodium tetrahydroborate; ozone 1.) EtOH, CHCl3, -78 degC; Yield given. Multistep reaction; |
(S)-4-Methyl-2-oxo-tetrahydro-furan-3-carboxylic acid
A
(S)-3-methyl-4-butanolide
B
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
at 180 - 200℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(R)-(+)-3-methyldihydrofuran-2,5-dione
A
(R)-3-methyl-γ-butyrolactone
B
(R)-3-methyl-dihydro-furan-2-one
Conditions | Yield |
---|---|
With hydrogen; magnesium sulfate; triethylamine; Ru2Cl4(DIOP)3 In toluene at 120℃; for 10h; Yield given. Title compound not separated from byproducts; |
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With sodium hydroxide for 5h; Cyclization; Lactonization; Hydrolysis; Heating; | 32.0 g |
(R)-4-hydroxy-3-methyl-butyronitrile
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Stage #1: (R)-4-hydroxy-3-methyl-butyronitrile With sodium hydroxide In ethanol Heating; Stage #2: With toluene-4-sulfonic acid In benzene Heating; |
(E)-4-hydroxy-3-methylbut-2-enoic acid
A
(S)-3-methyl-4-butanolide
B
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Stage #1: (E)-4-hydroxy-3-methylbut-2-enoic acid With chiral ruthenium catalyst; hydrogen; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl Stage #2: With hydrogen cation Further stages.; | |
With Ru(OAc)2((R)-BINAP); hydrogen Title compound not separated from byproducts.; |
4-methyl-2(5H)-furanone
A
(S)-3-methyl-4-butanolide
B
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With sodium tetrahydroborate; methyl-bis-((S)-4-phenyl-4,5-dihydro-oxazol-2-yl)-amine; cobalt(II) chloride In ethanol at 20℃; for 24h; Title compound not separated from byproducts; | |
With C32H12BF24(1-)*C37H44IrN2OP(1+); hydrogen In dichloromethane at 20℃; under 75007.5 Torr; for 24h; optical yield given as %ee; enantioselective reaction; |
(R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran for 5h; | |
With tetrabutyl ammonium fluoride In tetrahydrofuran |
4-methyl-2(5H)-furanone
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With Glycine max p51 reductase; NADPH In phosphate buffer at 36℃; for 12h; pH=7.0; |
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride |
3-Methylbutenoic acid
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 45 percent / SeO2 2.1: H2; BINAP; chiral ruthenium catalyst 2.2: H(1+) View Scheme |
MOM ether of (S)-(+)-methyl 3-hydroxy-2-methylpropionate
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 79 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature 2: 90 percent / pyridine / 0 - 5 °C 3: 90 percent / dimethylsulfoxide / 50 °C 4: 93 percent / aq. H2SO4 / aq. acetic acid / 1.5 h / Heating View Scheme |
(R)-(+)-2-methyl-3-methoxymethyloxypropan-1-ol
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / pyridine / 0 - 5 °C 2: 90 percent / dimethylsulfoxide / 50 °C 3: 93 percent / aq. H2SO4 / aq. acetic acid / 1.5 h / Heating View Scheme |
(S)-(+)-2-methyl-3-methoxymethyloxypropan-1-yl tosylate
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / dimethylsulfoxide / 50 °C 2: 93 percent / aq. H2SO4 / aq. acetic acid / 1.5 h / Heating View Scheme |
(R)-(+)-3-methyldihydrofuran-2,5-dione
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) calcium sulfate hemihydrate, 2.) molecular sieves 4 Angstroem / 1.) dioxane, 22 deg C, 45 h, lipozyme from Mucor miehei, 2.) cyclohexane, 22 deg C, 43 h, Novozym 435 from Candida antarctica 2: LiBH4 / tetrahydrofuran / 1 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: calcium sulfate hemihydrate / dioxane / 45 h / 22 °C / lipozyme from Mucor miehei 2: LiBH4 / tetrahydrofuran / 1 h / 50 °C View Scheme |
(R)-3-(tetrahydro-2-pyranyloxy)-2-methyl-1-propanol
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 95 percent / pyridine 2: 70 percent / dimethylsulfoxide / 48 h / Ambient temperature 3: 46 percent / conc. HCl / methanol / 7 h / Heating View Scheme |
(S)-3-(tetrahydro-2-pyranyloxy)-2-methylpropyl p-toluenesulfonate
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / dimethylsulfoxide / 48 h / Ambient temperature 2: 46 percent / conc. HCl / methanol / 7 h / Heating View Scheme |
(R)-3-methyl-γ-butyrolactone
4-bromo-3-methyl-butyric acid ethyl ester
Conditions | Yield |
---|---|
With hydrogen bromide In ethanol for 16h; Ambient temperature; | 96% |
With hydrogen bromide In ethanol |
ethanol
(R)-3-methyl-γ-butyrolactone
ethyl (R)-(+)-4-bromo-3-methylbutanoate
Conditions | Yield |
---|---|
With hydrogen bromide for 16h; Ambient temperature; | 96% |
Isobutyl iodide
(R)-3-methyl-γ-butyrolactone
(2R)-2,6-dimethylheptan-1-ol
Conditions | Yield |
---|---|
Stage #1: Isobutyl iodide With tert.-butyl lithium In diethyl ether; pentane at -78 - 20℃; Stage #2: (R)-3-methyl-γ-butyrolactone In diethyl ether; pentane at -78℃; for 3h; Further stages; | 79% |
Conditions | Yield |
---|---|
Stage #1: 1-Iodooctane With tert.-butyl lithium In diethyl ether; pentane at -78 - 20℃; for 1.5h; Stage #2: (R)-3-methyl-γ-butyrolactone In diethyl ether; pentane at -78℃; for 3h; Further stages; | 78% |
Conditions | Yield |
---|---|
Stage #1: 1-Iodohexane With tert.-butyl lithium In diethyl ether; pentane at -78 - 20℃; for 1.5h; Stage #2: (R)-3-methyl-γ-butyrolactone In diethyl ether; pentane at -78℃; for 3h; Further stages; | 75% |
(R)-3-methyl-γ-butyrolactone
prenyl bromide
A
(2R,3R)-3-methyl-2-(3-methyl-2-butenyl)-4-butanolide
B
(2S,3R)-3-methyl-2-(3-methyl-2-butenyl)-4-butanolide
Conditions | Yield |
---|---|
With lithium diisopropyl amide 1) THF, -78 deg C, 1 h, 2) -78 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given; |
methyl cyanoformate
(R)-3-methyl-γ-butyrolactone
3(R)-carbomethoxy-4(R)-methyldihydro-2(3H)-furanone
Conditions | Yield |
---|---|
With lithium diisopropyl amide 1.) THF, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 3h; Yield given. Multistep reaction; |
eschenmoser's salt
(R)-3-methyl-γ-butyrolactone
Conditions | Yield |
---|---|
With lithium diisopropyl amide 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 1 h, b) RT, overnight; Multistep reaction; |
(R)-3-methyl-γ-butyrolactone
(-)-(2E,4R)-5-methyl-2-hexen-4-ol
4(R)-methyl-5(R)-(1(S),4-dimethyl-2(E)-pentenyl)dihydro-2(3H)furanone
Conditions | Yield |
---|---|
Multistep reaction; |
(R)-3-methyl-γ-butyrolactone
(-)-(2E,4R)-5-methyl-2-hexen-4-ol
A
(3R,4S)-3-((E)-(S)-1,4-Dimethyl-pent-2-enyl)-4-methyl-dihydro-furan-2-one
B
4(R)-methyl-3(R)-(1(S),4-dimethyl-2(E)-pentenyl)dihydro-2(3H)-furanone
C
4(S)-methyl-3(S)-(1(S),4-dimethyl-2(E)-pentenyl)dihydro-2(3H)-furanone
D
4(R)-methyl-3(S)-(1(S),4-dimethyl-2(E)-pentenyl)dihydro-2(3H)-furanone
Conditions | Yield |
---|---|
In toluene at 110℃; for 48h; Product distribution; Mechanism; investigation of the steric course Claisen rearrangements of lactone; | |
With acid In toluene at 110℃; for 48h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(R)-3-methyl-γ-butyrolactone
trans-(R)-2-Octen-4-ol
(3R,4S)-4-Methyl-3-((E)-(S)-1-methyl-hept-2-enyl)-dihydro-furan-2-one
Conditions | Yield |
---|---|
With potassium tert-butylate; tert-butyl alcohol; Trimethylacetic acid 1) toluene, reflux, 2 d, 2) Et2O, 3 h, 25 degC; Yield given. Multistep reaction; |
(R)-3-methyl-γ-butyrolactone
trans-(R)-2-Octen-4-ol
A
4(R)-methyl-3(R)-(1(S)-methyl-2(E)-heptenyl)dihydro-2(3H)-furanone
B
4(R)-methyl-3(S)-(1(S)-methyl-2(E)-heptenyl)dihydro-2(3H)-furanone
Conditions | Yield |
---|---|
Multistep reaction. Title compound not separated from byproducts; |
(R)-3-methyl-γ-butyrolactone
trans-(R)-2-Octen-4-ol
4(R)-methyl-3(S)-(1(S)-methyl-2(E)-heptenyl)dihydro-2(3H)-furanone
Conditions | Yield |
---|---|
Multistep reaction. Title compound not separated from byproducts; |
The systematic name of 2(3H)-Furanone,dihydro-4-methyl-, (4R)- is (4S)-4-methyldihydrofuran-2(3H)-one. With the CAS registry number 65284-00-6, it is also named as (R)-beta-Methyl-gamma-butyrolactone. In addition, its molecular formula is C5H8O2 and its molecular weight is 100.11582.
The other characteristics of 2(3H)-Furanone,dihydro-4-methyl-, (4R)- can be summarized as: (1)ACD/LogP: -0.10; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0; (4)ACD/LogD (pH 7.4): 0; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 17; (8)ACD/KOC (pH 7.4): 17; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.431; (14)Molar Refractivity: 24.891 cm3; (15)Molar Volume: 96.249 cm3; (16)Polarizability: 9.867×10-24cm3; (17)Surface Tension: 29.379 dyne/cm; (18)Density: 1.04 g/cm3; (19)Flash Point: 74.98 °C; (20)Enthalpy of Vaporization: 44.287 kJ/mol; (21)Boiling Point: 206.624 °C at 760 mmHg; (22)Vapour Pressure: 0.235 mmHg at 25 °C.
People can use the following data to convert to the molecule structure.
(1)SMILES: O=C1OC[C@@H](C)C1
(2)InChI: InChI=1/C5H8O2/c1-4-2-5(6)7-3-4/h4H,2-3H2,1H3/t4-/m0/s1
(3)InChIKey: ALZLTHLQMAFAPA-BYPYZUCNBA
(4)Std. InChI: InChI=1S/C5H8O2/c1-4-2-5(6)7-3-4/h4H,2-3H2,1H3/t4-/m0/s1
(5)Std. InChIKey: ALZLTHLQMAFAPA-BYPYZUCNSA-N
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