146048
2-Adamantanone
ReagentPlus®, 99%
Synonym(s):
2-Oxoadamantane, Tricyclo[3.3.1.13,7]decanone (9CI)
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About This Item
Empirical Formula (Hill Notation):
C10H14O
CAS Number:
Molecular Weight:
150.22
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
211-847-2
Beilstein/REAXYS Number:
1210235
MDL number:
Product Name
2-Adamantanone, ReagentPlus®, 99%
InChI key
IYKFYARMMIESOX-SPJNRGJMSA-N
InChI
1S/C10H14O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9H,1-5H2/t6-,7+,8-,9+
SMILES string
O=C1C2CC3CC(C2)CC1C3
product line
ReagentPlus®
assay
99%
form
solid
mp
256-258 °C (subl.) (lit.)
functional group
ketone
Quality Level
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Application
2-Adamantanone was used in the synthesis of dispiro N-Boc-protected 1,2,4-trioxane and (+/-)-1-(adamantan-2-yl)-2-propanamine.
General description
2-Adamantanone on deprotonation in the gas phase affords the corresponding β-enolate anion. It reacts with 1,1-dilithio-1-sila-2,3,4,5-tetraphenylsilole to yield 5-silafulvene.
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
Regulatory Information
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Irina S Toulokhonova et al.
Journal of the American Chemical Society, 126(17), 5336-5337 (2004-04-29)
Reaction of 1,1-dilithio-1-sila-2,3,4,5-tetraphenylsilole with 2-adamantanone produces a 5-silafulvene. This represents a new method for synthesis of silenes, leading to the first example of a silapentafulvene.
Sunil Sabbani et al.
Bioorganic & medicinal chemistry letters, 18(21), 5804-5808 (2008-10-11)
Dispiro N-Boc-protected 1,2,4-trioxane 2 was synthesised via Mo(acac)(2) catalysed perhydrolysis of N-Boc spirooxirane followed by condensation of the resulting beta-hydroperoxy alcohol 10 with 2-adamantanone. N-Boc 1,2,4-trioxane 2 was converted to the amine 1,2,4-trioxane hydrochloride salt 3 which was subsequently used
Matthew M Meyer et al.
The Journal of organic chemistry, 75(12), 4274-4279 (2010-05-26)
Deprotonation of 2-adamantanone (1) in the gas phase affords the corresponding beta-enolate anion. This ion was independently prepared by the fluoride-induced desilylation of 4-trimethylsilyl-2-adamantanone, and its reactivity and thermodynamic properties were measured (DeltaH degrees(acid) = 394.7 +/- 1.4, EA =
W T Nolan et al.
International journal of radiation biology and related studies in physics, chemistry, and medicine, 39(2), 195-205 (1981-02-01)
The repair of sublethal radiation damage (SLD) in Chinese hamster (V79) cells was investigated as a function of temperature in the presence and absence of the membrane lipid perturbers, butylated hydroxytoluene (BHT) or adamantanone, which decrease the viscosity of the
E Mariani et al.
Il Farmaco; edizione scientifica, 35(5), 430-440 (1980-05-01)
The synthesis of (+/-)-1-(adamantan-2-yl)-2-propanamine (VI), its N,N-dimethyl derivative (VII) and other amines (VIII), (IX) and (X), starting from 2-adamantanone, is described. Some of these amines showed antiparkinson activity in mice.
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