371475

Sigma-Aldrich

2,2-Dimethylcyclopentanone

96%

Linear Formula:
(CH3)2C5H6(=O)
CAS Number:
Molecular Weight:
112.17
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

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-phosphabicyclo3.3.0octane family (PBO). It may be used in the synthesis of:
  • 2,6,6-trimethyl-2-azaspiro4.4nonane-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

Packaging

1, 5 g in glass bottle

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Risk Statement

10

Safety Statement

16-29-33

RIDADR

UN1224 - class 3 - PG 3 - Ketones, liquid, n.o.s., HI: all

WGK Germany

WGK 3

Flash Point(F)

91.4 °F - closed cup

Flash Point(C)

33 °C - closed cup

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)
Synthesis of pyrrolizidine oximes 222 and 236: Novel alkaloids of a dendrobatid poison frog.
Rutchinson KD, et al.
Tetrahedron, 50(21), 6129-6136 (1994)
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...
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...
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...
Articles
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.
Read More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.