Nerol
Conditions | Yield |
---|---|
With palladium diacetate; sodium azide; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 25℃; for 1h; | 98% |
Conditions | Yield |
---|---|
With isopropyl alcohol; zirconium(IV) oxide for 6h; Rate constant; Heating; | 97% |
With isopropyl alcohol; zirconium(IV) oxide for 6h; Heating; | 97% |
With sodium formate; RuCl2(m-SPPh2)2 In water at 80℃; for 7h; | 95% |
1-(tert-butyldimethylsiloxy)-3,7-dimethyl-2,6-octadiene
Nerol
Conditions | Yield |
---|---|
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.0833333h; | 95% |
In methanol; dichloromethane for 3.66667h; Irradiation; | |
In methanol; dichloromethane for 3.66667h; Product distribution; Irradiation; other silyl ethers; phenanthrene, var. time; |
Nerol
Conditions | Yield |
---|---|
With lithium; ethylenediamine In tetrahydrofuran at -10℃; for 2h; | 93% |
(Z)-1-(allyloxy)-3,7-dimethylocta-2,6-diene
Nerol
Conditions | Yield |
---|---|
With samarium diiodide; water; isopropylamine In tetrahydrofuran at 20℃; for 0.0333333h; | 88% |
Conditions | Yield |
---|---|
With indium tri-isopropoxide supported on mesoporous SBA-15 In isopropyl alcohol at 80℃; for 7h; Reagent/catalyst; Meerwein-Ponndorf-Verley Reduction; Inert atmosphere; Schlenk technique; chemoselective reaction; | 87.6% |
With potassium hydroxide; isopropyl alcohol; dichlorotetrakis(dimethylsulfoxide)ruthenium at 20℃; for 3h; | 86.8% |
With Triisopropyl borate; isopropyl alcohol at 27℃; for 20h; Kinetics; Reagent/catalyst; Meerwein-Ponndorf-Verley reduction; Inert atmosphere; chemoselective reaction; | 83.1% |
neryl 2-tetrahydropyranyl ether
Nerol
Conditions | Yield |
---|---|
ammonium cerium(IV) nitrate In alkaline aq. solution; acetonitrile at 70℃; for 2h; pH=8; Decomposition; | 86% |
With tin(ll) chloride In methanol Substitution; | 80% |
With boron trifluoride diethyl etherate; dimethylthio-dimethyl-tin In toluene at -20 - 0℃; for 12h; | 82 % Chromat. |
ethyl 3,7-dimethyl-2,6-octadienoate
Nerol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | 81% |
With diisobutylaluminium hydride In diethyl ether; hexane at -78 - 20℃; for 12.5h; | 0.9 g |
morpholide of 1-hydroxy-3,7-dimethylocta-2Z,6-diene-4-sulfonic acid
A
Nerol
B
2,6-dimethyl-2,5-octadien-8-ol
Conditions | Yield |
---|---|
With dibenzo-18-crown-6; sodium In tetrahydrofuran; benzene-d6 at -70℃; for 0.0333333h; | A 75% B 4% |
With dibenzo-18-crown-6; sodium In ammonia at -70℃; for 2h; | A 75% B 4% |
With sodium; tert-butyl alcohol In benzene-d6 at -70℃; Yield given. Yields of byproduct given; | |
With lithium; tert-butyl alcohol In ammonia at -70℃; Product distribution; also Na, (DB18C6) or Na, tBuOH in NH3; | |
With lithium In diethyl ether; ammonia at -65℃; Product distribution; other reagent, solvent, temperature; |
Conditions | Yield |
---|---|
With tris(2,4,6-trimethoxyphenyl)phosphine In methanol at 50℃; for 24h; | 73% |
Conditions | Yield |
---|---|
With bis-trimethylsilanyl peroxide; bis(acetylacetonate)oxovanadium In dichloromethane at 25℃; for 7h; | A 68% B 8% C 2% |
bis(acetylacetonate)oxovanadium; bis-trimethylsilanyl peroxide In dichloromethane at 25℃; for 7h; | A 68 % Chromat. B 8 % Chromat. C 2 % Chromat. |
bis(acetylacetonate)oxovanadium; bis-trimethylsilanyl peroxide In dichloromethane at 25℃; for 7h; Product distribution; | A 68 % Chromat. B 8 % Chromat. C 2 % Chromat. |
(2R*,3R*)-2,3-epoxy-3,7-dimethyl-6-octenyl acetate
A
3,7-dimethylocta-1,6-dien-3-ol
B
Nerol
Conditions | Yield |
---|---|
With tellurium; lithium triethylborohydride In tetrahydrofuran for 0.25h; Ambient temperature; | A 62% B 5.5% |
With tellurium; lithium triethylborohydride In tetrahydrofuran for 0.25h; Product distribution; Mechanism; Ambient temperature; other reducing Te agent; various time; also in the presence of fluoride ion; | A 62% B 5.5% |
2-methyl-3-buten-2-ol
A
Nerol
B
Geraniol
C
(+/-)-lavandulol
D
isoprene
Conditions | Yield |
---|---|
With oxalic acid In water for 5h; Heating; Further byproducts given. Yields of byproduct given; | A n/a B n/a C n/a D 46% |
Geraniol
A
Citronellol
B
Nerol
C
(E)-2,6-dimethyl-oct-2-ene-1,8-diol
D
(2E,6Z)-2,6-dimethylocta-2,6-diene-1,8-diol
E
8-hydroxygeraniol
Conditions | Yield |
---|---|
With 2,4-Dichlorophenoxyacetic acid; sucrose; cultured cells of Catharanthus roseus In water at 25℃; for 48h; Product distribution; other reaction time; | A n/a B n/a C 32.9% D 25.3% E 41.8% |
Conditions | Yield |
---|---|
With hydrogen bromide Behandeln des erhaltenen Bromids mit Kaliumacetat in Dimethylformamid und Erwaermen des Reaktionsprodukts mit wss.Natronlauge; | |
pyridine; tungsten oxomethoxide at 200℃; for 3h; | |
pyridine; tungsten oxomethoxide at 200℃; for 3h; Product distribution; other catalysts and time; |
aluminum isopropoxide
(E/Z)-3,7-dimethyl-2,6-octadienal
A
Nerol
B
Geraniol
C
acetone
Conditions | Yield |
---|---|
analoge Reaktionen mit Aldehyden und Ketonen bei hoeherer Temperatur; |
Conditions | Yield |
---|---|
With sodium amalgam; ethanol | |
With aluminum isopropoxide; isopropyl alcohol | |
With hydrotalcite; isopropyl alcohol at 82℃; for 5h; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
beim Kochen der Natriumverbindung; | |
With hydrogen iodide; benzene und Erwaermen des Reaktionsproduktes mit alkoh.Natronlauge; | |
With hydrogen iodide; acetic acid und Erwaermen des Reaktionsproduktes mit alkoh.Natronlauge; |
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid und Abspaltung von HBr aus dem Reaktionsprodukts; isolinalool; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride |
magnesium ethylate
isopropyl alcohol
(E/Z)-3,7-dimethyl-2,6-octadienal
A
Nerol
B
Geraniol
aluminum isopropoxide
isopropyl alcohol
(E/Z)-3,7-dimethyl-2,6-octadienal
A
Nerol
B
Geraniol
isopropyl alcohol
(E/Z)-3,7-dimethyl-2,6-octadienal
A
Nerol
B
Geraniol
Conditions | Yield |
---|---|
With magnesium ethylate | |
With magnesium ethylate |
Conditions | Yield |
---|---|
beim Erhitzen; |
Conditions | Yield |
---|---|
bis(acetylacetonate)oxovanadium; bis-trimethylsilanyl peroxide In dichloromethane at 25℃; for 12h; Product distribution; | A 5 % Chromat. B 8 % Chromat. C 2 % Chromat. |
With dodecansulfonic acid; water at 25℃; Rate constant; other acids, other solvent and temperature; |
2-(phenylthio)-3-methyl-3-buten-1-ol
prenyl bromide
A
Nerol
B
Geraniol
C
(+/-)-lavandulol
Conditions | Yield |
---|---|
With hexamethyldistannane In benzene at 25℃; for 5h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With indium; oxygen 1.) DMF, 1 h, RT, 2.) room temperature, 3 h; Yield given. Multistep reaction. Yields of byproduct given; |
(E/Z)-3,7-dimethyl-2,6-octadienal
A
Citronellol
B
3,7-dimethyl-oct-6-enal
C
Nerol
D
Geraniol
Conditions | Yield |
---|---|
With methanol; samarium diiodide In tetrahydrofuran for 24h; Ambient temperature; Yields of byproduct given. Title compound not separated from byproducts; | A 18 % Chromat. B 8 % Chromat. C n/a D n/a |
With methanol; samarium diiodide In tetrahydrofuran for 24h; Ambient temperature; Yields of byproduct given. Title compound not separated from byproducts; | |
With hydrogen; MgCo6Ge6 In hexane at 174.84℃; under 56255.6 Torr; for 2.5h; Product distribution; Further Variations:; Catalysts; Pressures; time; |
Conditions | Yield |
---|---|
With aluminum oxide; borane pyridine complex In cyclohexane for 10h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With carbon monoxide; water; hexarhodium hexadecacarbonyl; N,N,N'N'-tetramethyl-1,3-propanediamine In 2-ethoxy-ethanol at 30℃; under 7600 Torr; for 48h; | A 6 % Chromat. B 94 % Chromat. |
With formic acid In water; N,N-dimethyl-formamide Product distribution; the effect of the nature and concentration of the acid on the yield and ratio of the products of electrochemical hydrogenation, other reagent; | |
With sodium tetrahydroborate; ErCpCl2(THF)3 In methanol for 6h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(E/Z)-3,7-dimethyl-2,6-octadienal
A
Citronellol
B
Nerol
C
Geraniol
Conditions | Yield |
---|---|
With oxygen; Pd561phen60(OAc)180 In acetic acid; benzene at 60℃; for 24h; | 100% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In acetonitrile at 0℃; for 3h; pH=7; Inert atmosphere; | 100% |
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate In dichloromethane | 99% |
Conditions | Yield |
---|---|
With pyridine; dmap | 100% |
With pyridine; dmap for 18h; | 100% |
With dmap; triethylamine In dichloromethane at 0℃; for 0.333333h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 0.666667h; | 100% |
With pyridine In dichloromethane at 0℃; Inert atmosphere; | 100% |
With dmap; triethylamine at 0℃; for 3h; | 95% |
With N,N-dimethyl-aniline In diethyl ether for 2h; Heating; | 90% |
Nerol
tert-butylchlorodiphenylsilane
(Z)-1-[(tert-butyldiphenylsilyl)oxy]-3,7-dimethyl-2,6-octadiene
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 0.25h; Ambient temperature; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide | 99% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; | 98% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; | 98% |
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide for 3h; Ambient temperature; | 95% |
Nerol
[3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]methanol
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In chlorobenzene at 80℃; for 5h; | 100% |
With dihydrogen peroxide; Sucrose; molybdic acid In phosphate buffer at 2℃; for 48h; pH=7; | 92% |
With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In decane; dichloromethane at 20℃; for 1.5h; Inert atmosphere; | 75% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium hydroxide at 20℃; for 18h; | 100% |
With sodium hydride In tetrahydrofuran |
Conditions | Yield |
---|---|
With hydrogen; aluminum oxide; copper In isopropyl alcohol at 90℃; for 12h; | 100% |
With dichloro(η3:η2:η3-dodeca-2,6,10-triene-1,12-diyl)ruthenium(IV); caesium carbonate; isopropyl alcohol at 82℃; for 23h; Inert atmosphere; chemoselective reaction; | 95 %Chromat. |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction; | 99.9% |
With N,N′,N′′,N′′′-hexadecyltrimethylammonium bis(trifluoromethylsulfonyl)imide; Novozym 435 (immobilized Candida antarctica lipase B) at 50℃; for 4h; Green chemistry; Enzymatic reaction; | |
at 59.84℃; for 3h; | |
With dmap; dicyclohexyl-carbodiimide In dichloromethane Steglich Esterification; |
Conditions | Yield |
---|---|
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction; | 99.9% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane Steglich Esterification; |
Nerol
neryl chloride
Conditions | Yield |
---|---|
With N-chloro-succinimide; dimethylsulfide In dichloromethane at -40 - 0℃; for 2h; | 99% |
With chloro-trimethyl-silane; potassium carbonate In Petroleum ether at 0℃; for 2h; | 93% |
With dimethylsulfide; methanesulfonyl chloride; lithium chloride In N,N-dimethyl-formamide at 0 - 20℃; for 0.75h; Inert atmosphere; | 90% |
Nerol
(Z)-neryl bromide
Conditions | Yield |
---|---|
With carbon tetrabromide; triphenylphosphine In benzene at 0℃; for 2h; | 99% |
With carbon tetrabromide; triphenylphosphine In benzene at 0℃; for 2h; | 99% |
With 1H-imidazole; iodine In dichloromethane at 20℃; for 2h; | 91% |
diiodomethane
Nerol
<(1RS,2RS)-2-methyl-2-(4'-methyl-3'-pentenyl)cyclopropyl>methanol
Conditions | Yield |
---|---|
With samarium In tetrahydrofuran at -78 - 20℃; | 99% |
Nerol
trimethylsilylazide
O-(cis-3,7-dimethylocta-2,6-dien-1-yl)trimethylsilane
Conditions | Yield |
---|---|
tetrabutylammomium bromide at 30℃; for 0.00333333h; | 99% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction; | 98.7% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane Steglich Esterification; |
Conditions | Yield |
---|---|
With bis(pentafluorophenyl)borinic acid; magnesium sulfate; pivalaldehyde In toluene for 3h; Ambient temperature; | 98% |
With Ba In dichloromethane for 48h; | 95% |
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; toluene-4-sulfonic acid In dichloromethane 1) 0 deg C, 1 h, 2) r.t., 2 h; | 91% |
Nerol
(E)-3-Methyl-oct-2-en-6-yn-1-ol
Conditions | Yield |
---|---|
With sodium nitrite In water; acetic acid 1.) 0 deg C 2.) 60 deg C, 0.5 h; | 98% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -78 - 20℃; for 1.08333h; Inert atmosphere; Schlenk technique; Cooling with acetone-dry ice; | 98% |
With pyridine In dichloromethane at -78℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction; | 97.8% |
Nerol
diphenyldisulfane
(cis-3,7-Dimethyl-2,6-octadienyl) phenyl sulfide
Conditions | Yield |
---|---|
With tributylphosphine In tetrahydrofuran for 2h; Ambient temperature; | 97.2% |
Nerol
Chloroiodomethane
cis-1-(hydroxymethyl)-2-methyl-2-(4-methyl-3-pentenyl)cyclopropane
Conditions | Yield |
---|---|
With samarium; mercury dichloride In tetrahydrofuran at -78 - 20℃; | 97% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 7h; | 97% |
Stage #1: Nerol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 0 - 20℃; for 7h; |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 22℃; for 1h; Inert atmosphere; | 97% |
Nerol
propargyl bromide
(Z)-3,7-dimethyl-1-(prop-2-yn-1-yloxy)octa-2,6-diene
Conditions | Yield |
---|---|
Stage #1: Nerol With sodium hydride In tetrahydrofuran at 40℃; for 15h; Inert atmosphere; Stage #2: propargyl bromide In tetrahydrofuran at 40℃; for 7h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With sodium hydroxide; dipotassium peroxodisulfate; nickel(II) sulphate In dichloromethane; water for 24h; Ambient temperature; Yields of byproduct given; | A 94% B n/a |
With 6C16H36N(1+)*2Zn(2+)*4Na(1+)*[Bi2Zn2(ZnW9O34)2](14-); urea hydrogen peroxide adduct In acetonitrile at 70℃; for 1h; Ene Reaction; | A 89% B 11% |
With bis(cyclopentadienyl)dihydrozirconium; benzaldehyde In toluene at 110℃; for 8h; | A 83% B 12% |
Nerol
tert-butyldimethylsilyl chloride
1-(tert-butyldimethylsiloxy)-3,7-dimethyl-2,6-octadiene
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 1h; Ambient temperature; | 94% |
With diisopropylamine In dichloromethane at 20℃; for 5h; Inert atmosphere; | 64% |
Nerol
(+/-)-2,3-epoxygeraniol
Conditions | Yield |
---|---|
With sodium hydroxide; sodium tungstate; aluminium trichloride; dihydrogen peroxide; toluene-4-sulfonic acid; magnesium chloride In methanol Ambient temperature; | 94% |
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