3,7-dimethyloct-6-en-1-yn-3-ol
A
3,7-dimethyloct-6-en-3-ol
B
(S)-(+)-linalool
Conditions | Yield |
---|---|
With hydrogen In hexane at 50℃; under 760.051 Torr; for 10h; | A 1% B 99% |
Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester
A
linalool
B
(S)-(+)-linalool
Conditions | Yield |
---|---|
With sodium hydroxide; tellurium; rongalite In tetrahydrofuran; water at 50 - 55℃; for 3h; Title compound not separated from byproducts; | A n/a B 97% |
With sodium hydroxide; tellurium; sodium formaldehyde sulfoxylate In tetrahydrofuran for 2h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
3,7-dimethyl-octa-1,6-diene-3-ol-3-O-β-D-glucopyranoside
(S)-(+)-linalool
Conditions | Yield |
---|---|
With Na2HPO4-citric buffer; β-D-glycosidase at 37℃; for 90h; | 88% |
With Na2HPO4-citrate buffer; β-glucosidase In water at 37℃; for 90h; pH=4.0; Hydrolysis; | 88.2% |
(S)-Benzyl linalyl ether
(S)-(+)-linalool
Conditions | Yield |
---|---|
With ammonia; sodium In diethyl ether at -78℃; for 0.5h; | 88% |
(S)-6-Methyl-2-(S)-thiiranyl-hept-5-en-2-ol
(S)-(+)-linalool
Conditions | Yield |
---|---|
With triethyl borane; tri-n-butyl-tin hydride In toluene at 0℃; for 0.0833333h; | 84% |
(2S,3R)-3-(bromomethyl)-2-methyl-2-(4-methylpent-3-en-1-yl)oxirane
A
linalool
B
(S)-(+)-linalool
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -25℃; for 0.5h; Ring cleavage; | A n/a B 83% |
Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester
(S)-(+)-linalool
Conditions | Yield |
---|---|
With zinc copper; sodium iodide In tetrahydrofuran for 2h; Heating; | 78% |
With sodium hydroxide; tellurium; rongalite In tetrahydrofuran; water at 50 - 55℃; for 3h; Product distribution; further reagent ratios, temperature, reagent, reaction times; |
(2S,3S)-2,3-epoxygeraniol
(S)-(+)-linalool
Conditions | Yield |
---|---|
With 1H-imidazole; 2,6-dimethylpyridine; water; iodine; triphenylphosphine In 1,2-dichloro-ethane; benzene at 75 - 80℃; for 2h; Mechanism; stereospecific 1,3-transposition of various chiral 2,3-epoxy alcohols; | 77% |
With 1H-imidazole; 2,6-dimethylpyridine; water; iodine; triphenylphosphine In 1,2-dichloro-ethane; benzene at 75 - 80℃; for 2h; | 77% |
Multi-step reaction with 2 steps 1: 84 percent / CBr4; triphenylphosphine / CH2Cl2 / 0 °C 2: 83 percent / BuLi / hexane; tetrahydrofuran / 0.5 h / -25 °C View Scheme |
Toluene-4-sulfonic acid (2R,3S)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester
(S)-(+)-linalool
Conditions | Yield |
---|---|
With sodium hydroxide; tellurium; water; rongalite In tetrahydrofuran for 1h; | 66% |
(S)-5-Benzenesulfonyl-3,7-dimethyl-octa-1,6-dien-3-ol
A
(S)-(+)-linalool
B
(E)-(S)-3,7-Dimethyl-octa-1,5-dien-3-ol
Conditions | Yield |
---|---|
With disodium hydrogenphosphate; sodium amalgam In methanol at 25℃; for 2.5h; | A 65% B n/a |
(2S,3S)-2,3-epoxygeraniol
A
(S)-(+)-linalool
Conditions | Yield |
---|---|
With 1H-imidazole; iodine; triphenylphosphine In benzene at 75 - 80℃; for 4h; Product distribution; stereospecific 1,3-transposition of various chiral 2,3-epoxy alcohols; | A 5% B 5% C 61% |
A
(S)-(+)-linalool
Conditions | Yield |
---|---|
With Ph3P(OH)I In 1,2-dichloro-ethane; benzene at 70 - 80℃; for 1h; | A 55% B 40% |
Conditions | Yield |
---|---|
durch linalylesterphthalsaeures Strychnin; |
Conditions | Yield |
---|---|
iron(II) sulfate In toluene at 50℃; for 2h; Yield given. Yields of byproduct given; | |
zirconium(IV) sulfate In toluene at 50℃; for 1h; Yield given. Yields of byproduct given; |
Toluene-4-sulfonic acid (2R,3R)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester
A
linalool
B
(S)-(+)-linalool
Conditions | Yield |
---|---|
With sodium hydroxide; tellurium; sodium formaldehyde sulfoxylate In tetrahydrofuran for 5h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
4-(geranylseleno)-15-(p-toluenesulfonyl)<2.2>paracyclophane
A
3,7-dimethylocta-1,6-dien-3-ol
B
(S)-(+)-linalool
Conditions | Yield |
---|---|
With triethylamine; 3-chloro-benzenecarboperoxoic acid Product distribution; 1) CH2Cl2, -66 deg C to -40 deg C, 10 min, 2) -40 deg to room temperature; stereoselectivity; |
3(S)-Linalool β-D-(6'-O-β-L-Fucopyranosyl)glucopyranosid
A
D-glucose
B
(S)-(+)-linalool
C
1-deoxy-L-galactitol
Conditions | Yield |
---|---|
With citrate buffer at 40℃; for 5h; enzyme hesperidinase; |
3,7-dimethyl-octa-1,6-diene-3-ol-3-O-β-D-glucopyranoside
A
D-glucose
B
(S)-(+)-linalool
Conditions | Yield |
---|---|
With citrate buffer at 40℃; for 6h; enzyme hesperidinase; |
(S)-(+)-linalool
Conditions | Yield |
---|---|
With cellulase (Sigma type II) In water Ambient temperature; | 23 mg |
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
(3S)-linaloyl β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside
A
1-O-β-D-xylopyranosyl-(1,6)-β-D-glucopyranoside
B
(S)-(+)-linalool
Conditions | Yield |
---|---|
With water at 37℃; for 1.5h; pH 6.0; hydrolysis by glucosidases II from tea leaves (cv. Yabukita); hydrolysis rate 63.0percent; further glucosidases and acetone powder from tea leaves; |
Conditions | Yield |
---|---|
With tert-butylhypochlorite; sodium hydrogencarbonate Product distribution; multistep reaction; |
(2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol
A
linalool
B
(S)-(+)-linalool
Conditions | Yield |
---|---|
With 1H-imidazole; 2,6-dimethylpyridine; water; iodine; triphenylphosphine In 1,2-dichloro-ethane; benzene at 75 - 80℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(2S,3R)-3,7-dimethyl-2,3-epoxy-6-octen-1-ol
A
linalool
B
(S)-(+)-linalool
Conditions | Yield |
---|---|
With 1H-imidazole; 2,6-dimethylpyridine; water; iodine; triphenylphosphine In 1,2-dichloro-ethane; benzene at 75 - 80℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In diethyl ether at -90℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
linaloxymethyl butanoate
A
linalool
B
butyl butyrate
C
(S)-(+)-linalool
Conditions | Yield |
---|---|
With pseudomonas fluorescens lipase; butan-1-ol In octane for 48h; Yield given; | |
With Candida rugosa lipase; butan-1-ol In octane at 45℃; for 4.25h; Yield given; |
linaloxymethyl butanoate
butan-1-ol
A
linalool
B
butyl butyrate
C
(S)-(+)-linalool
Conditions | Yield |
---|---|
With Candida rugosa lipase In octane at 45℃; for 4.25h; | |
With Candida rugosa lipase In octane at 45℃; for 4.25h; Product distribution; various enzymes, solvents and temp.; |
(2S,3R)-3-Iodomethyl-2-methyl-2-(4-methyl-pent-3-enyl)-oxirane
(S)-(+)-linalool
Conditions | Yield |
---|---|
With water In diethyl ether; acetonitrile at 38℃; for 10h; reductive elimination; |
(S)-(+)-linalool
Conditions | Yield |
---|---|
With hydrogenchloride at 20℃; | 4.6 mg |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 89 percent / 3 Angstroem sieves; 3 M t-butylhydroperoxide; (+)-diethyl tartrate / titanium(IV) isopropoxide / 2,2,4-trimethyl-pentane; CH2Cl2 / 0.75 h / -25 °C 2: 84 percent / CBr4; triphenylphosphine / CH2Cl2 / 0 °C 3: 83 percent / BuLi / hexane; tetrahydrofuran / 0.5 h / -25 °C View Scheme | |
Multi-step reaction with 2 steps 2: 78 percent / zinc-copper couple, NaI / tetrahydrofuran / 2 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 91 percent / (+)-DIPT,m Ti(OiPr)4, t-BuOOH, molecular sieves 4 Angstroem / CH2Cl2 / -34 °C 2: 94 percent / NEt3, 4-dimethylaminopyridine / CH2Cl2 / -10 °C 3: Te-rongalite, aq. NaOH / tetrahydrofuran / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: 85 percent / (-)-DIPT, Ti(OiPr)4, t-BuOOH, molecular sieves 4 Angstroem / CH2Cl2 / -34 °C 2: 86 percent / NEt3, 4-dimethylaminopyridine / CH2Cl2 / -10 °C 3: Te-rongalite, aq. NaOH / tetrahydrofuran / 5 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: 91 percent / tert-BuOOH (TBHP), (+)-diisopropyl tartrate, Ti(O-i-Pr)4 / CH2Cl2 / -37 °C 2: Et3N, dimethylaminopyridine (DMAP) / CH2Cl2 / 15 h / -10 °C 3: 66 percent / tellurium, HOCH2SO2Na, NaOH, H2O / tetrahydrofuran / 1 h View Scheme |
(S)-(+)-linalool
3,7-dimethyloct-6-en-3-ol
Conditions | Yield |
---|---|
With oxygen; 5-ethyl-10-methyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]pteridin-5-ium perchlorate; hydrazine hydrate In acetonitrile at 25℃; under 760 Torr; for 5h; | 96% |
With hydrazine hydrate In chloroform at 25℃; under 760.051 Torr; for 24h; Reagent/catalyst; | 79 %Chromat. |
Conditions | Yield |
---|---|
With 1,2,2,6,6-pentamethylpiperidine; 1-methyl-1H-imidazole-3-oxide In chloroform at 40℃; for 8h; Inert atmosphere; | 95% |
t-butyldimethylsiyl triflate
(S)-(+)-linalool
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; | 90% |
(S)-(+)-linalool
(2RS,5S)-2-hydroxy-5-methyl-5-vinyltetrahydrofuran
Conditions | Yield |
---|---|
With pyridine; ozone In dichloromethane at -78℃; for 0.75h; | 88% |
(S)-(+)-linalool
Conditions | Yield |
---|---|
With N-Bromosuccinimide In dichloromethane for 48h; Ambient temperature; | 85% |
(S)-(+)-linalool
(S)-2-methyl-1,2,5-pentanetriol
Conditions | Yield |
---|---|
Stage #1: (S)-(+)-linalool With ozone In methanol; dichloromethane at -78℃; for 0.0833333h; Stage #2: With sodium tetrahydroborate In methanol; dichloromethane at 0℃; Further stages.; | 77% |
acetic anhydride
(S)-(+)-linalool
(S)-linalyl acetate
Conditions | Yield |
---|---|
With dmap; triethylamine at 20℃; for 10h; Acetylation; | 70% |
With pyridine; dmap at 90℃; for 44h; Acetylation; |
(S)-(+)-linalool
(1S,2R,5S)-(+)-2,6,6-trimethylbicyclo<3.2.0>heptan-endo-2-ol
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; di-μ-chloro-bis(1,5-cyclooctadiene)dicopper In diethyl ether at 20℃; for 5h; Reagent/catalyst; Inert atmosphere; UV-irradiation; | 68% |
(S)-(+)-linalool
(3S)-linalyl 2,3,4-tri-O-acetyl-6-O-<(3-C-acetoxymethyl)-2,3-di-O-acetyl-β-D-erythrofuranosyl>-β-D-glucopyranoside
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane Ambient temperature; | 62% |
Conditions | Yield |
---|---|
In dichloromethane for 12h; Ambient temperature; | 45% |
(S)-(+)-linalool
A
5-bromo-2,6,6-trimethyl-(5R)-tetrahydropyran-2-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: (S)-(+)-linalool With 2,2,4,6-tetrabromocyclohexa-2,5-dienone In nitromethane at 0℃; for 5h; Stage #2: With osmium(VIII) oxide; N-methyl-2-indolinone In tetrahydrofuran at 20℃; for 24h; Stage #3: With sodium periodate In tetrahydrofuran at 0 - 20℃; Further stages.; | A 13% B 25% |
Conditions | Yield |
---|---|
With pyridine; thionyl chloride | |
With Petroleum ether; phosphorus trichloride unter Kuehlung; | |
Multi-step reaction with 3 steps 1: toluene; HBr 2: AgNO3 3: K2CO3; benzene; PCl3 / 0 - 5 °C View Scheme |
(S)-(+)-linalool
A
geranyl chloride
B
(R)-3-chloro-3,7-dimethyl-octa-1,6-diene
Conditions | Yield |
---|---|
With phosphorus trichloride | |
With phosphorus trichloride |
Conditions | Yield |
---|---|
With hydrogen bromide; toluene |
Conditions | Yield |
---|---|
With formic acid l-α-terpineol; |
Conditions | Yield |
---|---|
With on fired clay applied aluminium oxide at 310℃; dl-limonene; |
(S)-(+)-linalool
phenyl isocyanate
phenylcarbamic acid-((R)-linalyl ester); carbanilic acid ester of d-linalool
Conditions | Yield |
---|---|
The CAS registry number of 1,6-Octadien-3-ol,3,7-dimethyl-, (3S)- is 126-90-9. The IUPAC name is (3S)-3,7-dimethylocta-1,6-dien-3-ol. Its EINECS registry number is 204-810-7. In addition, the molecular formula is C10H18O and the molecular weight is 154.25. It should be stored in a cool and dry place.
Physical properties about this chemical are: (1)ACD/LogP: 3.28; (2)ACD/LogD (pH 5.5): 3.28; (3)ACD/LogD (pH 7.4): 3.28; (4)ACD/BCF (pH 5.5): 183.44; (5)ACD/BCF (pH 7.4): 183.44; (6)ACD/KOC (pH 5.5): 1451.47; (7)ACD/KOC (pH 7.4): 1451.47; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 9.23 Å2; (12)Index of Refraction: 1.463; (13)Molar Refractivity: 49.5 cm3; (14)Molar Volume: 179.6 cm3; (15)Polarizability: 19.62 ×10-24cm3; (16)Surface Tension: 28.2 dyne/cm; (17)Density: 0.858 g/cm3; (18)Flash Point: 84.9 °C; (19)Enthalpy of Vaporization: 50.58 kJ/mol; (20)Boiling Point: 198.5 °C at 760 mmHg; (21)Vapour Pressure: 0.0905 mmHg at 25°C.
Preparation of 1,6-Octadien-3-ol,3,7-dimethyl-, (3S)-: it can be prepared by 6-methyl-2-thiiranyl-hept-5-en-2-ol. This reaction will need reagents Bu3SnH and Et3B, and solvent toluene. The reaction time is 5 minutes at reaction temperature of 0 °C. The yield is about 84%.
Uses of 1,6-Octadien-3-ol,3,7-dimethyl-, (3S)-: it can be used to get 5-(1-bromo-1-methyl-ethyl)-2-methyl-2-vinyl-tetrahydro-furan. This reaction will need reagent NBS and solvent CH2Cl2. The reaction time is 48 hours with ambient temperature. The yield is about 85%.
You can still convert the following datas into molecular structure:
(1)SMILES: O[C@@](/C=C)(C)CC/C=C(/C)C
(2)InChI: InChI=1/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3/t10-/m1/s1
(3)InChIKey: CDOSHBSSFJOMGT-SNVBAGLBBB
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