Conditions | Yield |
---|---|
With tert-butyldibutyltin chloride; sodium cyanoborohydride In tert-butyl alcohol at 33℃; for 18h; Ultrasound with 20 KHz and bubbling of air; | 100% |
With 2,2'-azobis(isobutyronitrile); PVS; N-ethylpiperidinium hypophosphite In 1,4-dioxane; water at 100℃; for 0.5h; | 72% |
With PVS; (CH3)3N(+)(CH2)15CH3*H2PO2(-); 4,4'-dicyano-4,4'-azo-di-valeric acid In water at 100℃; for 1h; | 70% |
Conditions | Yield |
---|---|
With Fe(AAEMA)3; oxygen; isovaleraldehyde In 1,2-dichloro-ethane under 760 Torr; for 60h; Ambient temperature; | 99% |
With oxone; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate In dichloromethane; water at 0 - 25℃; under 3878.71 Torr; for 0.0222222h; Reagent/catalyst; Temperature; Solvent; | 99% |
With water; bromine for 1h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; oxygen; caesium carbonate In dichloromethane at 40℃; for 40h; Irradiation; | 99% |
With manganese(IV) oxide; sulfuric acid at 25 - 30℃; | 82% |
Stage #1: 1-Adamantanecarboxylic acid With dipotassium hydrogenphosphate; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate In chloroform at 20℃; for 48h; Schlenk technique; Irradiation; Green chemistry; Stage #2: With sodium tetrahydroborate In methanol; chloroform for 0.5h; Green chemistry; | 40% |
2-(tricyclo[3.3.1.13,7]dec-1-yloxy)tetrahydro-2H-pyran
1-adamanthanol
Conditions | Yield |
---|---|
poly(4-vinylpyridinium) p-toluenesulfonate In tetrahydrofuran; ethanol at 75℃; for 50h; Hydrolysis; | 99% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In methanol; water for 1h; Ambient temperature; | 96% |
With methanol at 20℃; for 0.666667h; | 92% |
1-trimethylsiloxyadamantane
1-adamanthanol
Conditions | Yield |
---|---|
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.1h; Green chemistry; | 99% |
With poly (ethylene glycol)-sulfonated sodium montmorillonite nanocomposite In methanol at 20℃; for 0.333333h; | 96% |
With silicaphosphite (silphos), [PCl3-n(SiO2)n] In acetonitrile at 20℃; for 0.0333333h; | 95% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide In acetic anhydride; acetic acid; N,N-dimethyl-formamide at 0 - 10℃; for 4h; Substitution; Electrochemical reaction; | 98% |
With water; bromine for 1h; | 95.5% |
With hydrogenchloride In N,N-dimethyl-formamide at 105℃; for 0.5h; | 95% |
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h; Product distribution; | A n/a B 97% C n/a |
With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h; Yields of byproduct given; | A n/a B 97% C n/a |
With ammonium cerium(IV) nitrate; oxygen In acetonitrile for 5h; Ambient temperature; Irradiation; | A 5% B 85% C 5% |
1-adamanthanol
Conditions | Yield |
---|---|
With ytterbium(III) triflate In methanol at 50℃; for 36h; | 97% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); oxygen; tert-butyldibutyltin chloride; sodium cyanoborohydride In tert-butyl alcohol at 60℃; for 20h; Yields of byproduct given; | A n/a B 96% |
With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 24h; Schlenk technique; chemoselective reaction; | A 42% B n/a |
1-(tert-butyldimethylsiloxy)tricyclo[3.3.1.1]decane
1-adamanthanol
Conditions | Yield |
---|---|
With 2,5-bis(perfluorohexyl)-3,6-dichloro-1,4-benzoquinone In water; acetonitrile at 50℃; for 6h; | 96% |
With N-iodo-succinimide In methanol at 20℃; for 24h; | 69% |
sulfonic acid functionalized nanoporous silica In methanol at 35℃; for 24h; | 50 % Chromat. |
1-adamanthanol
Conditions | Yield |
---|---|
With zinc diacetate In methanol; dichloromethane at 38℃; for 30h; | 96% |
Conditions | Yield |
---|---|
Stage #1: adamantane; trifluoroacetic acid With oxygen; sodium nitrite at 20℃; for 3h; Stage #2: With hydrogenchloride Further stages.; | 96% |
adamantan-1-yl 4-methylbenzoate
1-adamanthanol
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In 1-methyl-pyrrolidin-2-one; isopropyl alcohol at 90℃; Electrochemical reaction; chemoselective reaction; | 95% |
With tetrabutylammonium tetrafluoroborate; isopropyl alcohol In 1-methyl-pyrrolidin-2-one at 90 - 100℃; Inert atmosphere; Electrolysis; | 95% |
(3S,5S,7S)-1-((4-methoxybenzyl)oxy)adamantane
1-adamanthanol
Conditions | Yield |
---|---|
With ammonium peroxydisulfate; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 20 - 30℃; for 5h; Irradiation; Green chemistry; | 95% |
1-(2-propenyloxy)tricyclo<3.3.1.13,7>decane
1-adamanthanol
Conditions | Yield |
---|---|
With tert.-butyl lithium In pentane at -78 - 20℃; Substitution; | 94% |
With 1,3-dimethylbarbituric acid; Pd(PPh3) In tetrahydrofuran at 90℃; for 24h; | 87% |
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 90℃; for 24h; | 86% |
1-adamanthanol
Conditions | Yield |
---|---|
Stage #1: 4-benzyloxy-butyric acid adamantan-1-yl ester With hydrogen; palladium on activated charcoal In tetrahydrofuran under 760 Torr; for 24h; Stage #2: With potassium tert-butylate In tetrahydrofuran for 0.166667h; | 93% |
1-adamantyl benzyl ether
1-adamanthanol
Conditions | Yield |
---|---|
With water; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In acetonitrile at 20℃; for 8h; | 93% |
With triphenylphosphine hydrobromide In acetonitrile at 100℃; for 0.5h; Microwave irradiation; sealed tube; | 83% |
Di(1-adamantyl)-tert-butylmethanol
A
1-adamanthanol
B
tert-butyl alcohol
Conditions | Yield |
---|---|
With n-butyllithium In N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at 20℃; Product distribution; | A 8.6% B 92.4% |
adamantane
3,3-dimethyldioxirane
A
2-Adamantanone
B
1-adamanthanol
C
1-adamantanol
D
1,3-adamantandiol
E
1-acetyloxyadamantane
Conditions | Yield |
---|---|
In acetone at 20℃; for 7.6h; Rate constant; Product distribution; Kinetics; | A 1.5% B 91.5% C 1% D 4.5% E 1.5% |
1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thione
1-adamanthanol
Conditions | Yield |
---|---|
With antimony triphenylsulphide In diethyl ether for 1h; Ambient temperature; | 91% |
With oxygen; thiophenol; antimony tris-benzenethiolate In diethyl ether for 0.5h; Ambient temperature; | 91% |
(3r,5r,7r)-adamantan-1-ylboronic acid
1-adamanthanol
Conditions | Yield |
---|---|
With rose bengal; triethylamine In ethanol at 25℃; for 12h; Schlenk technique; Irradiation; | 91% |
2-((3r,5r,7r)-adamantan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1-adamanthanol
Conditions | Yield |
---|---|
With rose bengal; triethylamine In ethanol at 25℃; for 12h; Schlenk technique; Irradiation; | 91% |
1-adamanthanol
Conditions | Yield |
---|---|
With trimethyltin(IV) hydroxide In 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere; chemoselective reaction; | 91% |
acetonitrile
trans-N,N'-bis(1-adamantyl)diazene
A
1,1'-Biadamantane
B
adamantane
C
1-adamanthanol
D
N-(1-adamantyl)acetamide
Conditions | Yield |
---|---|
With thianthrene cation radical perchlorate Ambient temperature; Further byproducts given; | A 3% B 0.3% C 0.6% D 90% |
acetonitrile
trans-N,N'-bis(1-adamantyl)diazene
A
1,1'-Biadamantane
B
1-adamanthanol
C
N-(1-adamantyl)acetamide
D
1-acetyladamantane
Conditions | Yield |
---|---|
With thianthrenium perchlorate Ambient temperature; Further byproducts given; | A 2.5% B 0.6% C 90% D 5.5% |
adamantane
A
1-adamanthanol
B
1-nitroadamantane
C
1-nitroxyadamantane
Conditions | Yield |
---|---|
With Nitrogen dioxide; ozone In dichloromethane at -78℃; for 0.5h; | A n/a B 90% C n/a |
With methanesulfonic acid; dinitrogen pentoxide In dichloromethane at 0℃; for 1h; |
Di(1-adamantyl)(1-norbornyl)methanol
A
1-adamanthanol
B
1-norbornyl alcohol
Conditions | Yield |
---|---|
With n-butyllithium In N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at 20℃; Product distribution; | A 89.7% B 10.3% |
1-adamantyl trifluoroacetate
1-adamanthanol
Conditions | Yield |
---|---|
With sodium hydroxide In water at 100℃; for 0.5h; | 89% |
With potassium hydroxide In ethanol; water at 25℃; for 0.5h; Yield given; | |
With sodium carbonate for 2h; Heating; Yield given; |
adamantane
trifluoroacetic acid
A
1-adamanthanol
B
2-adamantyl trifluoroacetate
Conditions | Yield |
---|---|
With peracetic acid; ruthenium trichloride In dichloromethane; ethyl acetate at 20℃; for 2h; | A 89% B 9% |
trityl tetrafluoroborate
1-<(methylthio)methoxy>tricyclo<3.3.1.13,7>decane
A
triphenylmethyl alcohol
B
1-adamanthanol
C
triphenmethyl methyl sulfide
Conditions | Yield |
---|---|
In dichloromethane for 0.25h; Ambient temperature; | A 77% B 88% C 16% |
In dichloromethane for 0.25h; Product distribution; Mechanism; Ambient temperature; quenching with aq. NaHCO3, other trityl salts; | A 77% B 88% C 16% |
Conditions | Yield |
---|---|
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 18h; | 100% |
With chlorosulfonic acid In chloroform at 10 - 15℃; for 8h; | 96% |
With indium(III) chloride; dimethylmonochlorosilane; benzil In dichloromethane at 20℃; for 82h; | 93% |
carbon disulfide
1-adamanthanol
methyl iodide
O-(adamantan-1-yl) S-methyl carbonodithioate
Conditions | Yield |
---|---|
Stage #1: carbon disulfide; 1-adamanthanol With 1H-imidazole; sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 0.5h; | 100% |
Stage #1: carbon disulfide; 1-adamanthanol With sodium hydride In tetrahydrofuran at 20℃; for 10h; Addition; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 1h; Methylation; | 78% |
Stage #1: 1-adamanthanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 2h; Stage #2: carbon disulfide In tetrahydrofuran; mineral oil at 0 - 20℃; for 15h; Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 0℃; for 2h; | 72% |
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid at 20℃; for 48h; Friedel Crafts alkylation; | 100% |
With sulfuric acid; acetic acid In dichloromethane at 20℃; for 24h; | 100% |
With sulfuric acid; acetic acid In dichloromethane at 20℃; for 48h; Friedel-Crafts Alkylation; Large scale; | 99% |
Conditions | Yield |
---|---|
With magnesium(II) perchlorate at 20℃; for 0.33h; | 100% |
With tin(IV) tetraphenylporphyrin perchlorate at 20℃; for 0.25h; | 99% |
With silica gel for 0.0583333h; Microwave irradiation; neat (no solvent); | 99% |
1-adamanthanol
4-bromo-4'-hydroxybiphenyl
4-(4'-bromophenyl)-2-(adamantan-1-yl)phenol
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid at 25℃; for 72h; Friedel-Crafts reaction; | 100% |
With sulfuric acid; acetic acid at 20℃; for 96h; | 100% |
With sulfuric acid; acetic acid at 20℃; for 96h; | 100% |
With sulfuric acid In acetone at 20℃; for 96h; Cooling with ice; | 100% |
Friedel-Crafts alkylation; |
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 4h; | 100% |
With phosphoric acid; acetic acid at 40 - 42℃; for 5h; | 100% |
Conditions | Yield |
---|---|
With N-Methyldicyclohexylamine; copper diacetate In toluene at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With trifluoroacetic acid at 20℃; for 6h; Inert atmosphere; | 100% |
With trifluoroacetic acid at 20℃; for 12h; | 85% |
With trifluoroacetic acid | 79% |
With sulfuric acid In dichloromethane at 20℃; Inert atmosphere; | 23% |
With sulfuric acid In dichloromethane at 20℃; Inert atmosphere; |
1-adamanthanol
cobalt(II) bis(trimethylsilyl)amide
Conditions | Yield |
---|---|
In benzene under Ar, refluxed briefly; filtered, washed with ether, elem. anal.; | 100% |
Conditions | Yield |
---|---|
With indium(III) triflate; acetylacetone for 2h; Reflux; Green chemistry; | 100% |
With trifluoroacetic acid at 20℃; for 12h; | 86% |
Conditions | Yield |
---|---|
With tungsten hexacarbonyl at 180℃; for 1h; chemoselective reaction; | 100% |
1-adamanthanol
2,3,4-tri-O-benzyl-L-rhamnopyranosyl ortho-hex-1-ynylbenzoate
Conditions | Yield |
---|---|
Stage #1: 1-adamanthanol; 2,3,4-tri-O-benzyl-L-rhamnopyranosyl ortho-hex-1-ynylbenzoate In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Molecular sieve; Stage #2: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; Molecular sieve; | 100% |
1-adamanthanol
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; Molecular sieve; Inert atmosphere; stereoselective reaction; | 100% |
Conditions | Yield |
---|---|
With triisopropylborane; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane 1.) -30 deg C, 30 min 2.) room temp., 6 h; | A 99.9% B 0.1% |
Conditions | Yield |
---|---|
Stage #1: 1-adamanthanol; chloroacetonitrile With sulfuric acid In acetic acid; N,N-dimethyl-formamide at 20 - 80℃; Stage #2: With water In acetic acid; N,N-dimethyl-formamide at 70℃; | 99.6% |
Stage #1: 1-adamanthanol; chloroacetonitrile With acetic acid In N,N-dimethyl-formamide Stage #2: With sulfuric acid; water In N,N-dimethyl-formamide at 20 - 80℃; Product distribution / selectivity; | 99.6% |
With sulfuric acid; acetic acid at 20℃; for 5h; Ritter reaction; | 95% |
With indium(III) triflate In sulfur dioxide at -50 - 100℃; for 24h; Ritter Amidation; Inert atmosphere; Autoclave; liquid SO2; | 79% |
Conditions | Yield |
---|---|
With copper(ll) bromide at 150℃; for 8h; Reagent/catalyst; Ritter Amidation; Inert atmosphere; Sealed tube; | 99% |
With trifluoromethylsulfonic anhydride; sodium hydrogencarbonate In dichloromethane for 2h; Ambient temperature; | 98% |
With water; tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 140℃; for 0.416667h; Ritter Amidation; Microwave irradiation; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With oxygen; 1,2-dibromomethane for 10h; Reflux; | 99% |
With iron(III)-acetylacetonate; carbon tetrabromide at 120℃; for 2h; Sealed tube; Inert atmosphere; | 99% |
With dibromo sulfoxide In toluene for 22h; | 96% |
Conditions | Yield |
---|---|
With hydrogen; aluminum oxide; nickel at 180℃; | 99% |
With indium(III) chloride; diphenylsilyl chloride In 1,2-dichloro-ethane at 80℃; for 3h; | 99% |
With boron trifluoride diethyl etherate In water for 2h; Inert atmosphere; Reflux; | 29% |
Conditions | Yield |
---|---|
With iron(III) chloride In 1,2-dichloro-ethane at 50℃; for 24h; Inert atmosphere; Sealed tube; | 99% |
With oxalic acid; 2,3,4,5-tetrafluorophenyl(dihydroxy)borane In nitromethane at 20℃; | 87% |
With sulfuric acid for 2h; | 66% |
1-adamanthanol
1,1,1,3,3,3-hexamethyl-disilazane
1-trimethylsiloxyadamantane
Conditions | Yield |
---|---|
iodine In dichloromethane at 20℃; for 0.1h; Substitution; | 99% |
With silica-supported ZnCl2 (30%) In acetonitrile at 20℃; for 0.35h; | 98% |
With aluminum tris(dihydrogen phosphate) at 20℃; for 0.933333h; | 97% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran | 99% |
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 20h; | 81% |
With sodium hydride In tetrahydrofuran | |
Stage #1: 1-adamanthanol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With zinc(II) fluoride In dichloromethane for 18h; | 99% |
Conditions | Yield |
---|---|
With copper(ll) bromide at 150℃; for 6h; Ritter Amidation; Inert atmosphere; Sealed tube; | 99% |
With bismuth(lll) trifluoromethanesulfonate; water Ritter reaction; | 91% |
With water; tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 140℃; for 0.416667h; Ritter Amidation; Microwave irradiation; Green chemistry; | 90% |
1-adamanthanol
2,3,4-tri-O-acetyl-L-rhamnopyranosyl (N-phenyl)-2,2,2-trifluoroacetimidate
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 25℃; for 3h; | 99% |
1-adamanthanol
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 25℃; for 3h; | 99% |
1-adamanthanol
25,27-bis(benzyloxy)-26,28-dihydroxycalix[4]arene
Conditions | Yield |
---|---|
With trifluoroacetic acid In chloroform at 60 - 65℃; for 9h; | 99% |
1. Introduction of 1-Adamantanol
1-Adamantanol is also called Tricyclo[3.3.1.1(3,7)]decan-1-ol ; Tricyclo[3.3.1.1]decan-1-ol ; 1-Adamantol ; 1-Adamatanol ; Damantol-(1) ; Tricyclo(3.3.1.1(sup3,7))decan-1-ol ; 1-Hydroxydiamantane.
2. Properties of 1-Adamantanol
Melting Point: 247 °C (subl.)(lit.)
Flash Point: 240°C
Boiling Point: 245.8 °C at 760 mmHg
Freely Rotating Bonds: 1
Polar Surface Area: 9.23 Å2
Index of Refraction: 1.58
Molar Refractivity: 43.71 cm3
Molar Volume: 131.1 cm3
Surface Tension: 49.3 dyne/cm
Enthalpy of Vaporization: 56.11 kJ/mol
Vapour Pressure: 0.00466 mmHg at 25°C
Appearance: white to off-white crystalline powder or needles
3. Structure Descriptors of 1-Adamantanol
InChI=1S/C10H16O/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9,11H,1-6H2
4. Toxicity of 1-Adamantanol
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 600mg/kg (600mg/kg) | Pharmaceutical Chemistry Journal Vol. 10, Pg. 454, 1976. |
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