371475
2,2-Dimethylcyclopentanone
96%
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About This Item
Linear Formula:
(CH3)2C5H6(=O)
CAS Number:
Molecular Weight:
112.17
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
96%
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.)
functional group
ketone
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
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
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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.
Baeyer-Villiger氧化是与羰基相邻的碳-碳键的氧化裂解，其可将酮转化为酯、环酮转化为内酯。
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 371475-1G | 04061836684884 |
| 371475-5G | 04061836684891 |