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371475

Sigma-Aldrich

2,2-Dimethylcyclopentanone

96%

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About This Item

Formule linéaire :
(CH3)2C5H6(=O)
Numéro CAS:
4541-32-6
Poids moléculaire :
112.17
Numéro MDL:
MFCD00049164
Code UNSPSC :
12352100
ID de substance PubChem :
24863111
Nomenclature NACRES :
NA.22

Pureté

96%

Indice de réfraction

n20/D 1.433 (lit.)

Point d'ébullition

143-145 °C (lit.)

Densité

0.894 g/mL at 25 °C (lit.)

Groupe fonctionnel

ketone

Chaîne SMILES 

CC1(C)CCCC1=O

InChI

1S/C7H12O/c1-7(2)5-3-4-6(7)8/h3-5H2,1-2H3

Clé InChI

FTGZMZBYOHMEPS-UHFFFAOYSA-N

Description générale

2,2-Dimethylcyclopentanone is a ketone. Synthesis of various C-2 substituted vitamin D derivatives with a 2,2-dimethylcyclopentanone unit in side chains has been reported. Regioselective synthesis of 2,2-dimethylcyclopentanone, via its enolate precursor regioselectively obtained using the 2-pyrrolidone magnesium salt, has been reported.

Application

2,2-Dimethylcyclopentanone enolate may be used as starting reagent in the enantioselective synthesis of chiral phosphines belonging to the P-aryl-2-phosphabicyclo[3.3.0]octane family (PBO). It may be used in the synthesis of:
  • 2,6,6-trimethyl-2-azaspiro[4.4]nonane-1,3-dione, a spirosuccinimide moiety of asperparaline A
  • novel spiropentanopyrrolizidine oxime alkaloids, namely 2′,3′,5′,6′,7′,7a′-hexahydro-2,2-dimethylspirocyclopentane-1
  • δ,δ-dimethyl-δ-valerolactone, via Baeyer-Villiger oxidation

Pictogrammes

Flame
GHS02

Mention d'avertissement

Warning

Mentions de danger

H226

Classification des risques

Flam. Liq. 3

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

91.4 °F - closed cup

Point d'éclair (°C)

33 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificats d'analyse (COA)

Lot/Batch Number
BCCM0669
BCCG4223
BCCB2000
BCBS1171V
BCBP3738V

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Regioselective Synthesis of 2, 2-Dimethylcyclopentanone Using 2-Pyrrolidone Magnesium Salt as Electrogenerated Base.
Bonafoux D, et al.
Synthetic Communications, 28(1), 93-98 (1998)
Edwin Vedejs et al.
Journal of the American Chemical Society, 125(14), 4166-4173 (2003-04-03)
A new class of chiral phosphines belonging to the P-aryl-2-phosphabicyclo[3.3.0]octane family (PBO) has been prepared by enantioselective synthesis starting from lactate esters and 2,2-dimethylcyclopentanone enolate 5. A selective enolate alkylation method has been developed for preparation of 9 and 10
Synthesis of catalpalactone.
Lane KJ and Pinder AR.
The Journal of Organic Chemistry, 47(16), 3171-3172 (1982)
Synthesis of pyrrolizidine oximes 222 and 236: Novel alkaloids of a dendrobatid poison frog.
Rutchinson KD, et al.
Tetrahedron, 50(21), 6129-6136 (1994)
Hiroshi Saito et al.
The Journal of steroid biochemistry and molecular biology, 136, 3-8 (2013-02-19)
Up to the present, numerous vitamin D derivatives have been synthesized, but most of them have straight side chains, and there are few publications described about in vitro and in vivo evaluations on bone by vitamin D derivatives. In our
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Articles

Baeyer-Villiger Oxidation Reaction

The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.

Baeyer-Villiger Oxidation Reaction

The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.

Baeyer-Villiger Oxidation Reaction

The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.

Baeyer-Villiger Oxidation Reaction

The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.

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