10334-26-6

Usage

Uses

Used in Dental Applications:
(1R)-(-)-Camphorquinone is used as a visible light photoinitiator for biomedical applications, particularly in dental surgery. It plays a crucial role in the curing of resin composites, ensuring effective and efficient dental restorations.
Used in Chemical Synthesis:
(1R)-(-)-Camphorquinone serves as a chiral starting material for the preparation of various compounds, including:
α-Hydroxycamphors, which are produced by selective reduction of keto groups using various vegetables.
Camphor-1,2-diamine platinum(II) complexes, which are utilized in DNA interaction studies.
Camphoric anhydride, obtained through unsensitized photo-oxidation in the presence of oxygen and polar solvents.
Camphorquinone-based chiral homoallylic amine, which reacts with aldehydes to produce homoallylic primary amines via imine formation followed by 2-azonia-Cope rearrangement.
Used in Analytical Chemistry:
(1R)-(-)-Camphorquinone may be used as an analytical standard for determining the analyte in dental resin composite restorations. It aids in the analysis of the oral environment when in contact with food, beverages, and biological samples through various analytical techniques.

Purification Methods

It can be purified by steam distillation, recrystallisation (yellow prisms) from EtOH, *C6H6 or Et2O/pet ether and it can be sublimed in a vacuum. The (±)-quinone forms needles from EtOH, m 197-198o, 203o. [Buxtorf & Flatt Helv Chim Acta 13 1026 1930, Asahena et al. Chem Ber 67 1432 1934, Beiltein 7 I 325.]

InChI:InChI=1/C10H14O2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6H,4-5H2,1-3H3/t6?,10-/m0/s1

Upstream product

• 76-22-2 Camphor 
• 7519-74-6 thiocamphor 
• 17697-12-0 benzeneseleninic anhydride 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 464-48-2 (1S)-camphor 
• 50-00-0 formaldehyd 
• 33162-63-9 3-endo-aminobornan-2-one 
• 67-66-3 chloroform 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 31571-14-9 (1R,E)-(+)-camphorquinone 3-oxime 
• 95589-30-3 (1S,2R,4R,4'R)-4'-Chloromethyl-4,7,7-trimethylbicyclo<2.2.1>heptane-2-spiro-2'-(1',3'-dioxolan)-3-one 
• 464-17-5 1,7,7-trimethylbicyclo[2.2.1]hept-2-ene 
• 64-19-7 acetic acid 
• 10373-81-6 3-hydroxy-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 

Downstream Products

• 595-29-9 camphoric anhydride 
• 15210-83-0 2,2,3-trimethyl-4-oxo-cyclohexanecarboxylic acid 
• 71681-69-1 (+/-)-3-((Ξ)-4-bromo-phenylimino)-bornan-2-one 
• 117122-83-5 (+/-)-3-((Ξ)-2-bromo-phenylimino)-bornan-2-one 
• 110463-08-6 (+/-)-3-(3-ethoxy-phenylimino)-bornan-2-one 
• 3278-94-2 homocamphorquinoline 
• 21488-68-6 (1R)-3exo-hydroxy-bornan-2-one 
• 10373-79-2 DL-3-endo-(4-Methyl-benzyl)-3-exo-hydroxy-bornan-2-on 
• 101980-80-7 1,2,2-trimethylcyclopentyl p-methylbenzyl ketone 
• 10373-80-5 DL-2-endo-(4-Methyl-benzyl)-2-exo-hydroxy-bornan-3-on 
• 101980-83-0 2,2,3-trimethylcyclopent-3-enyl p-methylbenzyl ketone 
• 101980-82-9 2,2-dimethyl-3-methylenecyclopentyl p-methylbenzyl ketone 
• 101980-84-1 cis-2,2,3-trimethylcyclopentyl p-methylbenzyl ketone 
• 101980-81-8 trans-2,3,3-trimethylcyclopentyl p-methylbenzyl ketone 

Relevant academic research and scientific papers

Synthesis of 1,11,11-trimethyl-3,6-diazotricyclo [6.2.1.0 2,7]undeca-2,6-diene and 1,15,15-trimethyl-3,10-diazotetracyclo[10.2. 1.02,11.04,9]pentadeca-2,4(9),5,7,10-pentaene from camphoroquinone enantiomers

Optically active camphordihydro-2,3-pyrazine and camphorquinoxaline were prepared from camphoroquinone enantiomers. It was shown that (1S,4R)-(+)-camphoroquinone was formed by oxidation of (1S,3R, 4R)-(-)-3-bromocamphor and (1R,4S)-(-)-camphoroquinone from (1R,3S, 4S)-(+)-3-bromocamphor, respectively. Camphor anhydride was a side product (6-10%) of the reaction. Springer Science+Business Media, Inc. 2007.

An improved synthesis of camphorquinone-3-oxime

Camphorquinone 3-oxime is prepared in 77% yield in one step from camphor. The synthesis avoids the use of toxic selenium reagents, and provides the syn compound as the major stereoisomer.

Synthesis of terpene diamines based on camphor-derived dinitriles

Diamines are useful as additional ligands in enantioselective hydrogenations. A new route for synthesizing such a rigid diamine from naturally available camphor via camphor oxime/camphor furoxan/deoxygenation in large scale was developed. The resulting dinitriles were subjected to hydrogenation with Raney Ni or other heterogenous catalysts. In most cases, the reduction resulted in complex mixtures. The best results were obtained with Raney Ni in THF/H2O in strongly basic media (NaOH), which affords compound 5b only in good yield. Homogenous catalyst like Grubbs 2nd generation reduced only the less hindered CN group to yield an amino nitrile.

The Role of Side-Arms for Supramolecular Affinity Materials Based on 9,9′-Spirobifluorenes

An eightfold functionalized D2d-symmetric 9,9′-spirobifluorene was condensed with a collection of diketones with elaborated structural features to form three-dimensional supramolecular architectures with active surfaces. Gas-sorption measuremen

Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Chiral O,N,O-tridentate Phenol Ligands Derived from Camphor

Chiral O,N,O-tridentate phenol ligands bearing a camphor backbone were found to be effective chiral catalysts for the enantioselective addition of diethylzinc to aromatic aldehydes, resulting in high enantioselectivities (80-95% ee) at room temperature.

Synthesis and evaluation of camphor and cytisine-based cyanopyrrolidines as DPP-IV inhibitors for the treatment of type 2 diabetes mellitus

In this study, bornyl- and cytisine-based cyanopyrrolidines as potent dipeptidyl peptidase-IV (DPP-IV) inhibitors were synthesised. The in vitro inhibiting activities of bornyl- and cytisine derivatives towards DPP-IV were evaluated. Bornyl-based cyanopyrrolidines were shown to have moderate inhibitory activity with regard to DPP-IV (1.27–15.78 μM). A docking study was performed to elucidate the structure-activity relationship of the obtained compounds. The in vivo hypoglycemic activities of the same compounds were evaluated with the oral glucose tolerance test (OGTT) in mice. Bornyl-based cyanopyrrolidines were shown to have good hypoglycemic activity.

An environment friendly preparation of 3-bromocamphor and camphorquinone

The bromination of camphor has been carried out on a multi-gram scale by a mixture of KBr and KBrO3 in the presence of acid or with HBr/NaBr - H+ and H2O2/oxone as the oxidant. The 3-bromocamphor is then efficiently converted to camphorquinone by an improved oxidation protocol using DMSO and sodium carbonate of tetrabutyl ammonium iodide.

Stereoselective cyclopalladation of 2,3-camphorquinone 3-diphenylmethylimine

A reaction of (1R,4 S)-3-diphenylmethylimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one with lithium tetrachloropalladate gives a palladium(II) complex with a monodentately coordinated ligand, whereas chiral palladacyclic compounds are formed in the case o

Efficient synthesis of camphorquinone from camphor

In this study, we discussed an efficient approach for the synthesis of camphorquinone from camphor by the continuous reaction of bromination and oxidation. The oxidation of 3-bromocamphor was catalyzed by Fe-porphyrins with air. The catalytic activity of iron-metallated functional porphyrins was investigated under optimization conditions. The results showed that this method was a milder alternative to the reported methods, with a simple, greener procedure in which the advantages were the utilization of air as the oxidant and the use of metalloporphyrins as catalysts. Copyright Taylor & Francis Group, LLC.

(+)-Camphor and (?)-borneol derivatives as potential anti-orthopoxvirus agents

Although the World Health Organisation had announced that smallpox was eradicated over 40 years ago, the disease and other related pathogenic poxviruses such as monkeypox remain potential bioterrorist weapons and could also re-emerge as natural infections