106033-56-1

Basic information

• Product Name: Cyclohexanone, 2,2,6-trimethyl-, (R)-
• CAS NO: 106033-56-1
• Molecular Formula: C9H16O
• Molecular Weight: 140.225
• Mol File: 106033-56-1.mol

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, 2,2,6-trimethyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 2,2,6-trimethyl-, (R)-(106033-56-1)
• EPA Substance Registry System: Cyclohexanone, 2,2,6-trimethyl-, (R)-(106033-56-1)

Safety Data

• Hazardous Substances Data: 106033-56-1(Hazardous Substances Data)

Upstream product

• 1193-47-1 2,2-dimethyl-cyclohexanone 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 83999-44-4 2,6,6-trimethyl-1-trimethylsilyloxycyclohexene 
• 362044-40-4 (-)-(1S,6R)-2,2,6-trimethylcyclohexanol 
• 60046-49-3 (6R)-levodione 

Relevant articles and documents

Asymmetric organocatalytic protonation of silyl enolates catalyzed by simple and original betaines derived from Cinchona alkaloids

The asymmetric protonation of silyl enolates derived from tetralone, benzosuberone, and cyclohexanone has been successfully achieved by using simple and original betaine catalysts derived from Cinchona alkaloids (quinine and quinidine series) to afford th

Rate of deprotonation of a simple ketone by lithium diisopropylamide

Rate studies on deprotonation of a simple ketone (R-2,2,6- trimethylcyclohexanone) with lithium diisopropylamide are described. The data are consistent with the reaction being first order in ketone and half order in the base, corresponding to the rate equation: v = k[ketone][LDA](1/2).

Asymmetric protonation of lithium enolates of alpha-amino acid derivatives with alpha-amino acid-based chiral Bronsted acids.

The reaction of lithium enolates of alpha-amino acid derivatives with chiral amides, easily synthesized from L-tert-leucine, gives corresponding optically active unnatural alpha-amino acid derivatives with up to 87% ee.

Catalytic Enantioselective Protonation of Lithium Enolates with Chiral Imides

The catalytic enantioselective protonation of simple enolates was achieved using a catalytic amount of chiral imides and stoichiometric amount of achiral proton sources. Among the achiral proton sources examined in the protonation of the lithium enolate of 2,2,6-trimethylcyclohexanone catalyzed by (S,S)-imide 1, 2,6-di-tert-butyl-p-cresol (BHT) and its derivatives gave the highest enantiomeric excess. For example, 90% ee of (R)-enriched ketone was obtained when (S,S)-imide 1 (0.1 equiv) and BHT (1 equiv) were used. Use of 0.01 equiv of the chiral catalyst still caused a high level of asymmetric induction. For catalytic protonation of the lithium enolate of 2-methylcyclohexanone, chiral imide 6 possessing a chiral amide portion was superior to (S,S)-imide 1 as a chiral proton source and the enolate was effectively protonated with up to 82% ee.

Enantioselective protonation of silyl enolates catalyzed by a Binap·AgF complex

Silver lining: A catalytic enantioselective protonation of trimethylsilyl enolates uses a binap/silver(I) fluoride complex as a chiral catalyst in a mixture of dichloromethane and methanol (see scheme). Various ketones with tertiary asymmetric carbon cent

Organocatalyzed enantioselective protonation of silyl enol ethers: Scope, limitations, and application to the preparation of enantioenriched homoisoflavones

In the present work, enantioselective protonation of silyl enol ethers is reported by means of a variety of chiral nitrogen bases as catalysts, mainly derived from cinchona alkaloids, in the presence of various protic nucleophiles as proton source. A detailed study of the most relevant reaction parameters is disclosed allowing high enantioselectivities of up to 92% ee with excellent yields to be achieved under mild and eco-friendly conditions. The synthetic utility of this organocatalytic protonation was demonstrated during the preparation of two homoisoflavones 4a and 4b, isolated from Chlorophytum Inornatum and Scilla Nervosa, which were obtained with 81% and 78% ee, respectively.

Effects of lithium salts on the enantioselectivity of protonation of enolates with chiral imide

An increase in enantioselectivity was observed in the asymmetric protonation of prochiral enolates with a chiral imide using lithium salt as an additive. For example, (R)-enriched 2-n-pentylcyclopentanone 6 was obtained in high yield with 90% ee when the silyl enol ether 4 was treated with n-BuLi in the presence of 5 equiv of LiBr in Et2O and the resulting lithium enolate 5 was then protonated by a solution of (S,S)-imide 1 in THF. In contrast, the product 6 obtained without LiBr exhibited a lower enantiomeric excess (74% ee).

Enantioselective protonation of prochiral enolates with chiral imides

New chiral proton sources possessing an asymmetric 2-oxazoline ring, (S,S)-imide 1 and related imides, were synthesized from Kemp's triacid and optically active 2-amino alcohols. With these chiral imides, various lithium enolates of α-monoalkylated cycloalkanones were effectively protonated with excellent to moderate enantioselectivity. An increase in enantioselectivity was observed in the asymmetric protonation of prochiral enolates with (S,S)- imide 1 using lithium salt as an additive. For example, (R)-enriched 2-n- pentylcyclopentanone 35 was obtained in high yield with 90% ee when the silyl enol ether 33 was treated with n-BuLi in the presence of 5 equiv of LiBr in Et2O, and the resulting lithium enolate 34 was then protonated by a solution of (S,S)-imide 1 in THF. In contrast, the product 35 obtained without LiBr exhibited a lower enantiomeric excess (74% ee).

ENANTIOSELECTIVE DEPROTONATION OF TWO RACEMIC CYCLIC CARBONYL COMPOUNDS BY A CHIRAL LITHIUM AMIDE

The cyclic carbonyl compounds 2 and 8 have been obtained in optical active form (o.y. 46percent and 36percent, respectively) from the racemic compounds by a deprotonation/protonation sequence, using chiral lithium amide 1.The optical activity of 2 is caus