28070-26-0

Upstream product

• 18530-01-3 Acetic acid (1S,4R)-3-bromo-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-en-2-yl ester 
• 100-52-7 benzaldehyde 
• 74636-48-9 C₁₀H₁₄LiO^(1-)*Li⁽¹⁺⁾ 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 100-58-3 phenylmagnesium bromide 
• 473929-46-3 (1R,4R)-3-[(E)-(dimethylamino)methylidene]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 75-36-5 acetyl chloride 

Downstream Products

• 87420-27-7 [(1R)-exo]-3-exo-(diphenylmethyl)borneol 
• 118205-69-9 (1R,3R,4R)-3-benzyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 38253-64-4 (1R,3S,4R)-3-benzyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 91419-02-2 3-trans-benzylideneisobornyl acetate endo-oxide 
• 91419-02-2 3-trans-benzylideneisobornyl acetate exo-oxide 
• 91419-01-1 3-trans-benzylideneisoborneol endo-oxide 
• 91419-01-1 3-trans-benzylideneisoborneol exo-oxide 
• 77078-79-6 3-exo-benzyl-1,7,7-trimethylbicyclo<2.2.1>heptane-3-endo-2-exo-diol 
• 77078-79-6 3-endo-benzyl-1,7,7-trimethylbicyclo<2.2.1>heptane-2-exo-3-exo-diol 
• 28070-25-9 3-trans-benzylideneisobornyl acetate 
• 28070-24-8 3-trans-benzylideneisoborneol 
• 15087-24-8 3-benzylidene-dl-camphor 
• 864851-06-9 1,2,2-trimethyl-3-styryl-cyclopentanecarboxylic acid 
• 21653-28-1 3-benzhydryl-1,7,7-trimethyl-norbornan-2-one 

Relevant academic research and scientific papers

Synthesis and structural characterization of novel camphor-derived amines

Two novel 4-substituted camphidine derivatives 10a,b have been prepared from (+)-camphor (1) in five steps, the Beckmann rearrangement being the bottleneck of the synthesis. Isoborneol derivative 5b, formed as a side product during the hydrogenation of arylidene ketone 3b, under Beckmann rearrangement conditions yielded interesting novel rearrangement products 11 and 12. (1S)-(+)-Camphorquinone (13) was transformed into diamines 15 and 16 in two steps, the former being cyclized into an imidazoline salt 17, an N-heterocyclic carbene precursor. The structures of all novel compounds have been meticulously characterized using NMR techniques and/or single crystal X-ray analysis. Copyright

Synthesis and structural elucidation of novel camphor-derived thioureas

Nine novel (+)-camphor-derived thioureas have been prepared. 3-((Dimethylamino)methylene)camphor (2) served as the common precursor for the preparation of both, 2-thiourea 15-20 and 3-thiourea functionalized camphor derivatives 6, 7/7′, respectively. Starting from 2, the latter were prepared in two or three steps whereas the former in five steps, respectively. Configuration of all novel compounds has been meticulously determined using NMR techniques and/or single crystal X-ray crystallography. Copyright

Simple and effective protocol for Claisen-Schmidt condensation of hindered cyclic ketones with aromatic aldehydes

A simple and effective methodology for Claisen-Schmidt condensation of (-)-menthone and other hindered cyclic ketones with aromatic aldehydes under highly basic conditions using a polar aprotic solvent and a strong base (alkali metal hydroxide or an alkoxide) is described and discussed. Georg Thieme Verlag Stuttgart.

A class II aldolase mimic

A class II aldolase-mimicking synthetic polymer was prepared by the molecular imprinting of a complex of cobalt (II) ion and either (1S,3S,4S)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (4a) or (1R,3R,4R)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (4b) in a 4-vinylpyridine-styrene-divinylbenzene copolymer. Evidence for the formation of interactions between the functional monomer and the template was obtained from NMR and VIS titration studies. The polymers imprinted with the template demonstrated enantioselective recognition of the corresponding template structure, and induced a 55-fold enhancement of the rate of reaction of camphor (1) with benzaldehyde (2), relative to the solution reactions, and were also compared to reactions with a series of reference polymers. Substrate chirality was observed to influence reaction rate, and the reaction could be competitively inhibited by dibenzoylmethane (6). Collectively, the results presented provide the first example of the use of enantioselective molecularly imprinted polymers for the catalysis of carbon-carbon bond formation.

Stereoselective additions to the exocyclic C{double bond, long}C bond of some α-alkylidene-(+)-camphor derivatives

Stereoselective additions to the exocyclic C{double bond, long}C double bond of some (1R,3E,4S)-3-alkylidene-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones and (1R,4E,5S)-4-alkylidene-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones were studied. All additions took place predominantly from the less hindered endo-face of the methylidene compounds to give the corresponding exo-adducts as the major isomers. Thus, catalytic hydrogenations afforded the α-alkylated (1R,3R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones and (1R,4R,5R)-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones in 28-100% de. Similarly, 1,3-dipolar cycloadditions of 2,4,6-trisubstituted benzonitrile oxides gave the corresponding spiro cycloadducts in 66-100% de. The structures were determined by 2D NMR techniques, NOESY spectroscopy and X-ray diffraction.

Synthesis and properties of benzylidene derivatives of terpenoid ketones

Optically active benzylidene derivatives of camphor and menthone were obtained in preparative yields by condensation of the ketones with aromatic aldehydes in DMSO in the presence of t-BuOLi. The synthesized α,β-unsaturated ketones show high specific rotation and thus are suitable to bedoping component to liquid-crystalline compositions.