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146048

Sigma-Aldrich

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:
700-58-3
Molecular Weight:
150.22
Beilstein:
1210235
EC Number:
211-847-2
MDL number:
MFCD00074737
UNSPSC Code:
12352100
PubChem Substance ID:
24848757
NACRES:
NA.22

Quality Level

100

product line

ReagentPlus®

Assay

99%

form

solid

mp

256-258 °C (subl.) (lit.)

SMILES string

O=C1C2CC3CC(C2)CC1C3

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+

InChI key

IYKFYARMMIESOX-SPJNRGJMSA-N

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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.

Application

2-Adamantanone was used in the synthesis of dispiro N-Boc-protected 1,2,4-trioxane and (+/-)-1-(adamantan-2-yl)-2-propanamine.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP8642
MKCJ4671
MKCF9794
MKBX0223V
08919HE

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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
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.
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 =
A Corma et al.
Nature, 412(6845), 423-425 (2001-07-27)
The Baeyer-Villiger oxidation, first reported more than 100 years ago, has evolved into a versatile reaction widely used to convert ketones-readily available building blocks in organic chemistry-into more complex and valuable esters and lactones. Catalytic versions of the Baeyer-Villiger oxidation
An adamantanone derivative that is an original modulator of redox processes in the cytochrome P-450 system can serve as an effective remedy against obliterating angiopathy of lower extremities.
I E Kovalev et al.
Doklady. Biochemistry and biophysics, 391, 201-203 (2003-10-09)
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