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371475

Sigma-Aldrich

2,2-Dimethylcyclopentanone

96%

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Linear Formula:
(CH3)2C5H6(=O)
CAS Number:
4541-32-6
Molecular Weight:
112.17
MDL number:
MFCD00049164
UNSPSC Code:
12352100
PubChem Substance ID:
24863111
NACRES:
NA.22

Quality Level

200

Assay

96%

refractive index

n20/D 1.433 (lit.)

bp

143-145 °C (lit.)

density

0.894 g/mL at 25 °C (lit.)

SMILES string

CC1(C)CCCC1=O

InChI

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

InChI key

FTGZMZBYOHMEPS-UHFFFAOYSA-N

Related Categories

General description

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

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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Synthesis of catalpalactone.
Lane KJ and Pinder AR.
The Journal of Organic Chemistry, 47(16), 3171-3172 (1982)
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 pyrrolizidine oximes 222 and 236: Novel alkaloids of a dendrobatid poison frog.
Rutchinson KD, et al.
Tetrahedron, 50(21), 6129-6136 (1994)
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)
S Tanimori et al.
Bioscience, biotechnology, and biochemistry, 64(8), 1758-1760 (2000-09-19)
2,6,6-Trimethyl-2-azaspiro[4.4]nonane-1,3-dione (9), a spirosuccinimide moiety of asperparaline A (1), was synthesized by starting from 2,2-dimethylcyclopentanone (4) via trinitrile 6 in five steps in a moderate yield. This conversion establishes a model study for synthesis of the spirosuccinimide moiety of asperparaline
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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.

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