Norborneol
Norbornan-2-on
Conditions | Yield |
---|---|
With tert.-butylnitrite; oxygen; acetic acid In toluene at 50℃; for 9h; | 99% |
With oxygen; Nafion polymer anchored ruthenium oxide pyrochlore composite In acetone at 20℃; under 760.051 Torr; for 12h; | 98% |
With γ-picolinium chlorochromate; silica gel In dichloromethane at 20℃; for 13h; | 97% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide In acetic acid for 10h; Ambient temperature; | 95% |
With perfluoro-cis-2-n-butyl-3-n-propyloxaziridine In various solvent(s) Ambient temperature; | 94% |
With nitrosonium tetrafluoroborate In various solvent(s) for 96h; Ambient temperature; | 55% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide In acetic acid for 10h; Ambient temperature; | 95% |
With perfluoro-cis-2-n-butyl-3-n-propyloxaziridine In various solvent(s) Ambient temperature; | 90% |
With potassium chlorochromate on SiO2 In dichloromethane for 80h; Ambient temperature; | 80% |
norborn-2-ene
A
2,3-epoxynorbornane
B
Norbornan-2-on
C
Norborneol
Conditions | Yield |
---|---|
With (PF6)2; oxygen In acetonitrile at 65℃; under 2068.6 Torr; Mechanism; Product distribution; also in the presence of H2O2; other alkene; also hydroxylation of cyclohexane; | A 94% B n/a C n/a |
With oxygen; isobutyraldehyde In acetonitrile at 60℃; for 1h; | A 91% B n/a C n/a |
With oxygen In acetone at -72℃; under 2 - 2.5 Torr; for 0.75h; Product distribution; Mechanism; | |
With dihydrogen peroxide; C18H22O7V In water; acetonitrile at 80℃; for 6h; Catalytic behavior; | |
With dihydrogen peroxide; C23H29N6O7V2(1-)*H2O*H(1+) In methanol at 70℃; for 6h; Catalytic behavior; Reagent/catalyst; |
Conditions | Yield |
---|---|
In toluene | 85% |
Norbornan-2-on
Conditions | Yield |
---|---|
With 1-n-butylpyridinium tetrachloroferrate; pyridinium chlorochromate at 50℃; for 0.416667h; | 84% |
bicyclo[2.2.1]heptan-2-one oxime
A
Norbornan-2-on
Conditions | Yield |
---|---|
With chloroperoxidase from fungus Caldaromyces fumago; dihydrogen peroxide; potassium bromide In water for 4h; | A 17% B 82% |
(+-)-methyl-[2exo]norbornyl ether
Norbornan-2-on
Conditions | Yield |
---|---|
With HOF* CH3CN; sodium fluoride In chloroform; water; acetonitrile 0 deg C -> room temperature; | 80% |
endo-2-methoxybicyclo<2.2.1>heptane
Norbornan-2-on
Conditions | Yield |
---|---|
With HOF* CH3CN; sodium fluoride In chloroform; water; acetonitrile 0 deg C -> room temperature; | 80% |
Norbornan-2-on
Conditions | Yield |
---|---|
With 1-n-butylpyridinium tetrachloroferrate; pyridinium chlorochromate at 50℃; for 0.333333h; | 80% |
N'-Bicyclo[2.2.1]hept-(2Z)-ylidene-N,N-dimethyl-hydrazine
Norbornan-2-on
Conditions | Yield |
---|---|
With ferric nitrate In dichloromethane 30 min., r.t., then reflux; | 79% |
exo-2,3-epoxynorbornane
Norbornan-2-on
Conditions | Yield |
---|---|
With [iron(III)(5,10,15,20-tetraphenyl-21H,23H-porphine)] perchlorate In 1,4-dioxane at 80℃; for 3h; | 77% |
Conditions | Yield |
---|---|
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile Heating; | 75% |
With nitronium tetrafluoborate In various solvent(s) for 168h; Ambient temperature; | 70% |
With sodium periodate; ruthenium tetroxide In acetonitrile at 40℃; for 96h; | 92 % Turnov. |
Conditions | Yield |
---|---|
With lithium perchlorate In diethyl ether for 1h; Ambient temperature; | 70% |
thionorcamphor
Norbornan-2-on
Conditions | Yield |
---|---|
With oxygen In tetrachloromethane Irradiation; | 67% |
With oxygen In methanol Product distribution; Mechanism; Irradiation; var. solvents, times, and yields, rate of (1)O2 quenching, efficiency of (1)O2 generation, stability; | 63% |
norborn-2-ene
diisobutylaluminium hydride
A
Norbornan-2-on
exo-2-norbornanol
(+/-)-endo-2-norborneol
D
3-isobutylbicyclo<2.2.1>heptan-2-one
E
2,2'-exo-binorbornane
Conditions | Yield |
---|---|
With oxygen; zirconium(IV) chloride In toluene at 20℃; Product distribution; further reagents; | A 1% B 62% C 16% D 8% E 4% |
(E)-exo-2-bromo-3'-phenylbicyclo<2.2.1>heptan-endo-3-spiro-2'-oxirane
A
Norbornan-2-on
B
benzyl alcohol
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene Heating; | A 35% B 60% |
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene Mechanism; Heating; diff. bicyclo<2.2.1>heptan-3-spiro-2'-oxiranes; | A 35% B 60% |
Conditions | Yield |
---|---|
With lithium diisopropyl amide In diethyl ether; hexane at -78℃; for 2h; | A 15% B 60% |
bicyclo[2.2.1]heptan-2-one oxime
A
Norbornan-2-on
Conditions | Yield |
---|---|
With chloroperoxidase from fungus Caldaromyces fumago; potassium chloride; dihydrogen peroxide In water for 4h; | A 39% B 59% |
endo-2-norbornyl methyl ether
acetonitrile
A
Norbornan-2-on
exo-2-norbornylacetamide
Conditions | Yield |
---|---|
With nitrosonium tetrafluoroborate at 0℃; for 6h; | A 58% B 10% |
With nitrosonium tetrafluoroborate at 0℃; for 15h; | A 58% B 10% |
Norbornan-2-on
Conditions | Yield |
---|---|
In para-xylene for 24h; Inert atmosphere; Reflux; | 58% |
With sodium bromate; Rexyn 101 H resin at 20℃; for 8h; | |
With tert.-butylhydroperoxide; [Fe(N-(2-pyridylmethyl)iminodiethanolate)(NO3)]2(NO3)2*2CH3OH In methanol; dodecane at 50℃; for 24h; Catalytic behavior; Reagent/catalyst; |
Conditions | Yield |
---|---|
nickel at 135 - 140℃; for 48h; Heating; | A 53% B 7% |
nickel at 135 - 140℃; for 36h; Heating; | A 42% B 7% |
2-hydroxy-2-norbornanecarboxylic acid
Norbornan-2-on
Conditions | Yield |
---|---|
In water | 53% |
In water | 50% |
exo-2-norbornyl chloride
Norbornan-2-on
Conditions | Yield |
---|---|
With silver(I) nitrite; antimony pentafluoride 1.) Freon-113, -30 deg C, 30 min, 2.) -25 deg C, 2 h then 0 deg C, 3 h; | 52% |
Conditions | Yield |
---|---|
With silver(I) nitrite In diethyl ether for 2h; 1.) 0 deg C, 2 h then room temp., 40 h; | A 50% B 38% C n/a D n/a |
exo-2-norbornyl methyl ether
acetonitrile
A
Norbornan-2-on
exo-2-norbornylacetamide
Conditions | Yield |
---|---|
With nitrosonium tetrafluoroborate at 0℃; for 6h; | A 33% B 16% |
Conditions | Yield |
---|---|
nickel at 135 - 140℃; for 24h; Heating; | A 32% B 4% |
Conditions | Yield |
---|---|
nickel at 135 - 140℃; for 24h; Heating; | A 30% B 5% |
Conditions | Yield |
---|---|
With chromium(VI) oxide; acetic anhydride; acetic acid In dichloromethane | 29% |
Norbornan-2-on
N,N-phenylbistrifluoromethane-sulfonimide
2-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-2-ene
Conditions | Yield |
---|---|
Stage #1: Norbornan-2-on With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; for 3h; Inert atmosphere; | 100% |
With n-butyllithium; diisopropylamine In tetrahydrofuran | 59% |
Norbornan-2-on
1-Bromo-4-fluorobenzene
2-(4-fluorophenyl)bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
Stage #1: 1-Bromo-4-fluorobenzene With iodine; magnesium In tetrahydrofuran at 0℃; for 4h; Stage #2: Norbornan-2-on In tetrahydrofuran at 0 - 20℃; Stage #3: With water In tetrahydrofuran | 99% |
With magnesium | |
Stage #1: 1-Bromo-4-fluorobenzene With iodine; magnesium In tetrahydrofuran Cooling with ice; Inert atmosphere; Stage #2: Norbornan-2-on In tetrahydrofuran at 20℃; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water pH=7; |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol at 10 - 15℃; | 97% |
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In methanol | 97% |
With hydroxylamine hydrochloride; sodium acetate In methanol Heating; | 85% |
With hydroxylamine hydrochloride; sodium acetate In methanol; water at 60℃; | 76% |
Conditions | Yield |
---|---|
With lithium diisobutyl-tert-butylaluminium hydride In tetrahydrofuran; hexane at -78℃; for 3h; | 97% |
With potassium dihydrobis(1-pyrazolyl)borate In ethanol at 20℃; for 24h; Reduction; | 91% |
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid / methanol 2: NaBH4 / propan-2-ol; H2O / 16 h / Ambient temperature View Scheme | |
Stage #1: Norbornan-2-on With Al-methanesulfonyldiisobutylalane In diethyl ether at 25℃; for 1h; Inert atmosphere; Stage #2: With hydrogenchloride; water In diethyl ether for 2h; Inert atmosphere; stereoselective reaction; | 51 %Chromat. |
With trans-[(2-(diphenylphosphanyl)-N-(pyridine-2-ylmethyl)ethaneamine)RuCl2(PPh3)]*dichloromethane; potassium tert-butylate; hydrogen In isopropyl alcohol at 60℃; under 7500.75 Torr; for 1h; Catalytic behavior; Inert atmosphere; Autoclave; | 96.6 %Chromat. |
Conditions | Yield |
---|---|
With benzophenone; potassium tert-butylate In 1,4-dioxane at 90℃; for 0.5h; Friedlaender synthesis; Inert atmosphere; | 97% |
With potassium hydroxide; benzophenone; dichlorotetrakis(dimethyl sulfoxide)ruthenium(II) In 1,4-dioxane at 80℃; for 24h; | 75% |
With benzophenone; potassium tert-butylate In 1,4-dioxane at 90℃; for 0.5h; Inert atmosphere; Schlenk technique; Glovebox; |
Norbornan-2-on
methylmagnesium bromide
(1R,2S,4S)-2-Methyl-bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
In diethyl ether for 0.5h; | 96% |
Conditions | Yield |
---|---|
With acyltransferase from Mycobacterium smegmatis; dihydrogen peroxide; ethyl acetate In water at 35℃; for 7h; Baeyer-Villiger Ketone Oxidation; Enzymatic reaction; | 96% |
With oxone; silica gel In dichloromethane at 20℃; for 8h; Baeyer-Villiger oxidation; | 95% |
With Oxone at 40℃; for 7h; Baeyer-Villiger oxidation; Ionic liquid; | 95% |
Norbornan-2-on
benzylamine
endo-N-benzyl-2-aminonorbornane
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 6h; Ambient temperature; | 95% |
With sodium tris(acetoxy)borohydride In tetrahydrofuran for 6h; Ambient temperature; |
Conditions | Yield |
---|---|
With ethylenediamine for 14h; Heating; | 95% |
Conditions | Yield |
---|---|
Stage #1: Norbornan-2-on; benzyl azide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 2.5h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at 0℃; for 1h; | 95% |
Norbornan-2-on
ethyl acetate
exo-ethyl (2-hydroxy-bicyclo[2.2.1]hept-2-yl)acetate
Conditions | Yield |
---|---|
Stage #1: ethyl acetate With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 0.166667h; Stage #2: Norbornan-2-on In tetrahydrofuran Reformatsky reaction; cooling; | 95% |
Norbornan-2-on
ethyl iodoacetae
exo-ethyl (2-hydroxy-bicyclo[2.2.1]hept-2-yl)acetate
Conditions | Yield |
---|---|
With manganese; copper(l) iodide; trifluoroacetic acid In acetonitrile at 20℃; for 12h; Reformatsky Reaction; Schlenk technique; Inert atmosphere; | 95% |
With nickel(II) iodide; manganese; trifluoroacetic acid In acetonitrile at 20℃; for 12h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With formic acid; C18H24Cl2IrN3 In water at 20℃; for 12h; Schlenk technique; Green chemistry; | 94% |
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran for 48h; Ambient temperature; |
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 2.5h; | 94% |
Norbornan-2-on
2,2-dihydroperoxybicyclo[2.2.1]heptane
Conditions | Yield |
---|---|
With dihydrogen peroxide In water; acetonitrile at 20℃; for 1.33333h; | 94% |
Norbornan-2-on
Norborneol
Conditions | Yield |
---|---|
With magnesium; mercury dichloride In ethanol at 20℃; for 12h; | 93% |
With isopropyl alcohol; Ni(0) nanoparticles In tetrahydrofuran at 76℃; for 1h; | 58% |
With sodium tetrahydroborate at 60℃; for 48h; | 30% |
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 2.5h; | 93% |
Norbornan-2-on
2-exo-ethynylbicyclo<2.2.1>heptan-2-ol
Conditions | Yield |
---|---|
In tetrahydrofuran Ambient temperature; | 92% |
Norbornan-2-on
lithium enolate of ethyl fluoroacetate
Fluoro-(2-hydroxy-bicyclo[2.2.1]hept-2-yl)-acetic acid ethyl ester
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether at -85℃; | 91% |
Norbornan-2-on
1-azido-4-chloro-butane
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 2.5h; | 91% |
pyrrolidine
Norbornan-2-on
1-(bicyclo[2.2.1]hept-2-ylidene)pyrrolidinium hexafluorophosphate
Conditions | Yield |
---|---|
With ammonium hexafluorophosphate In toluene for 2h; Reflux; | 91% |
Conditions | Yield |
---|---|
Stage #1: Norbornan-2-on; benzylamine With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: With ammonia borane In tetrahydrofuran at 20℃; for 8h; Inert atmosphere; | 91% |
Norbornan-2-on
(2-aminophenyl)(phenyl)methanone
9-phenyl-1,2,3,4-tetrahydro-1,4-methanoacridine
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate at 60℃; for 0.5h; Friedlaender synthesis; Ionic liquid; | 91% |
Norbornan-2-on
oxalic acid diethyl ester
ethyl 2-hydroxy(3-oxobicyclo[2.2.1]hept-2-ylidene)ethanoate
Conditions | Yield |
---|---|
Stage #1: Norbornan-2-on; oxalic acid diethyl ester With sodium hydride In tetrahydrofuran at 60℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran | 91% |
Reported in EPA TSCA Inventory.
Norcamphor(CAS NO.497-38-1) is a chemical compound, classified as a ketone, which is an analog of camphor without the three methyl groups. Itis a colorless to white adhering crystals. It is found in wood of the camphor laurel (Cinnamomum camphora), a large evergreen tree found in Asia (particularly in Borneo and Taiwan) and also of Dryobalanops aromatica, a giant of the Bornean forests. It also occurs in some other related trees in the laurel family, notably Ocotea usambarensis. It can also be synthetically produced from oil of turpentine. It is used as a chemical building block in organic synthesis.
Physical properties about Norcamphor are: (1)ACD/LogP: 0.892; (2)ACD/LogD (pH 5.5): 0.89; (3)ACD/LogD (pH 7.4): 0.89; (4)ACD/BCF (pH 5.5): 2.80; (5)ACD/BCF (pH 7.4): 2.80; (6)ACD/KOC (pH 5.5): 72.79; (7)ACD/KOC (pH 7.4): 72.79; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.511; (10)Molar Refractivity: 30.465 cm3; (11)Molar Volume:101.71 cm3; (12)Polarizability: 12.077 10-24cm3; (13)Surface Tension: 37.9020004272461 dyne/cm; (14)Density: 1.083 g/cm3; (15)Flash Point: 33.889 °C; (16)Enthalpy of Vaporization: 40.641 kJ/mol; (17)Boiling Point: 169.999 °C at 760 mmHg; (18)Vapour Pressure: 1.5 mmHg at 25°C
When you are using Norcamphor, please be cautious about it as the following:
1. Keep away from sources of ignition - No smoking;
2. Take precautionary measures against static discharges;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C7H10O/c8-7-4-5-1-2-6(7)3-5/h5-6H,1-4H2;
(2)InChIKey=KPMKEVXVVHNIEY-UHFFFAOYSA-N;
(3)SmilesC1[C@@H]2C(C[C@@H]1CC2)=O
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 180mg/kg (180mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04039, |
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View