20536-50-9

Upstream product

• 473-62-1 (1S,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]heptan-3-one 
• 14575-93-0 isopinocamphone 
• 7785-70-8 (+)-α-pinene 
• 7785-26-4 (-)-α-pinene 
• 276253-82-8 tert-butyl 2-[(E)-((1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo-[3.1.1]heptan-3-ylidene)amino]acetate 
• 329710-76-1 2-(trifluoromethoxy)ethyl trifluoromethanesulphonate 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 80-56-8 rac-α-pinene 
• 126003-99-4 (1R,2R,5R)-3-[(E)-(S)-1,2-Diphenyl-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol 
• 126003-97-2 (1R,2R,5R)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 138175-23-2 (1R,2R,5R)-2,6,6-Trimethyl-3-[(E)-pyridin-2-ylmethylimino]-bicyclo[3.1.1]heptan-2-ol 

Downstream Products

• 499-75-2 carvacrol 
• 503-93-5 eucarvone 
• 1196-00-5 (-)-isopinocampheol 
• 125423-98-5 [(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 125423-98-5 [(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 328000-60-8 (1R,2R,5R)-3-(4,5-Diphenyl-1,3-oxazol-2-ylmethylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 

Relevant academic research and scientific papers

Chiral Titanium(IV) Complexes Containing Polydentate Ligands Based on α-Pinene. Catalytic Activity in Sulfoxidation with Hydrogen Peroxide

The reaction of TiCl4-n(OiPr)n (n = 0, 2, 4) with various terpenoid preligands based on α-pinene, C7H6Me3(OH)(NCH2CH2G) (G = NH2, I; NHMe, II; OH, III), stereoselectively affords a series of new chiral titanium(IV) complexes. Such complexes are either octahedral, [TiCl2X(OC7H6Me3NCH2CH2G-κ3N,N,O)] (X = Cl, G = NH2, 1; X = OiPr, G = NH2, 2; G = NHMe, 3), or trigonal bipyramidal, [Ti(OiPr)3(OC7H6Me3NCH2CH2G-κ2N,O)] (G = NH2, 4; NHMe, 5) and [TiX(OiPr)(OC7H6Me3NCH2CH2O-κ3N,O,O?)] (X = Cl, 6; OiPr, 8), depending on the acidity of titanium, the reaction conditions and the nature of the pendant ending group of the terpenoid ligand. Density functional theory (DFT) calculations have been carried out to assess the stability of the multiple possible diastereoisomers allowing us to propose structural suggestions. The new titanium complexes efficiently catalyze the selective oxidation of various types of sulfides to either sulfoxides or sulfones using aqueous hydrogen peroxide, under mild conditions. All compounds have been characterized by multinuclear NMR spectroscopy and the molecular structure for some of them has been determined by X-ray diffraction.

Synthesis and characterization of new palladium complexes based on polydentate chiral Schiff base and amines ligands derived from (+)-2-hydroxypinan-3-one

Seven novel palladium complexes of the type [Pd(HL)Cl2] and [Pd(L)Cl] containing chiral pinane ligands (HL = 3-[(2-aminoethyl)imino]-pinane-2-ol; 3,3′-(ethylenediimino)bis-pinane-2-ol; cis-3-(2-aminoethylamino)-pinane-2-ol; cis-3,3′(ethylenediamino)bis-pinane-2-ol; trans-3,3′(ethylenediamino)bis-pinane-2-ol; 3-[2-(2-hydroxybenzylamino)ethylamino]-pinane-2-ol; L = 3-[2-(3,5-di-tert-butyl-2-hydroxybenzylidene)aminoethylimino]pinane-2-ol) were synthesized in good yields from the direct reaction of chiral nitrogen ligands with Li2PdCl4 in MeOH. These synthesized complexes were characterized by means of elemental analysis, FT-IR, multidimensional and multinuclear NMR spectroscopic methods.

Synthesis and physical chemical properties of 2-amino-4-(trifluoromethoxy)butanoic acid-a CF3O-containing analogue of natural lipophilic amino acids

2-Amino-2-(trifluoromethoxy)butanoic acid (O-trifluoromethyl homoserine) was synthesized as a racemate and in both enantiomeric forms. The measured pKa and log D values establish the compound as a promising analogue of natural aliphatic amino acids.

NOVEL SYNTHESIS INTERMEDIATES FOR OBTAINING DERIVATIVES OF SPHINGOSINES, CERAMIDES AND SPHINGOMYELINS WITH GOOD YIELDS

The subject matter of the present invention is the novel molecules of formulae E, E′ and F. These molecules prove to be synthesis intermediates that are very advantageous for the manufacture of derivatives of sphingosine or of ceramides functionalized in position 1, with good yields, in which R1 and R2 are fatty chains, R3 is an alkyl group and R4 is a protective group for alcohol functions. Another subject of the invention is the use of the intermediates of type F for converting same into intermediates of type G, by means of reduction in the presence of lithium borohydride. The G molecules are precursors that are known to make it possible to obtain sphingolipids or sphingomyelin.

New chiral ligands derived from (+) and (-)-α-pinene for the enantioselective addition of diethylzinc to aldehydes

In this study, we synthesized five new chiral ligands from (+) and (-)-α-pinene, which were successfully employed in the stereoselective addition of diethylzinc to aldehydes, leading to secondary chiral alcohols in up to 99% yield and 94% e.e.

Synthesis of chiral 1,2-diamines from α-pinene and their use in asymmetric nitroaldol reaction

Abstract Chiral diamines with C 1 and C 2 symmetry have been synthesized from 2-hydroxypinan-3-one and tested as ligands in Cu-catalyzed asymmetric nitroaldol reaction of nitromethane with 4-nitrobenzaldehyde.

New chiral cyclopalladated complexes based on the pinane and bornane imines

2α-Hydroxypinan-3-one imino derivatives react with lithium tetrachloropalladate to form palladacycles, while similar bornane derivative undergo cyclopalladation only when treated with palladium acetate.

Novel α-pinene-derived mono- and bisphosphinite ligands: Synthesis and application in catalytic hydrogenation

Novel mono- and bisphosphinite (-)-pinane-based ligands have been synthesized from (-)-α-pinene. Mixed with [(COD)2Rh] +[BF4]-, these ligands displayed moderate up to high catalytic activity in hydrogenation of dimethyl itaconate with dihydrogen. It has been observed that the structure of the ligand, the reaction temperature and solvent are important to define productivity of the phosphinite-based Rh-catalysts. Bisphosphinite ligands in hydrogenation reactions suffered from an Arbuzov rearrangement, leading to fast deactivation of the hydrogenation catalyst. In contrast, monophosphinite-derived Rh-catalysts showed increased productivity as well as thermal stability. An almost quantitative conversion of dimethyl itaconate has been achieved at elevated temperatures in toluene. Alternatively, hydrogenation of dimethyl itaconate with monophosphinite ligands has been carried out in MeOH at room temperature or 40 °C and has led to a nearly quantitative conversion.

Chiral imines and amines based on 2-hydroxypinan-3-one

The new chiral derivatives of benzylamine and 2α-hydroxypinan-3-one (1R,2R,5R)-3-[(1S)-α-methylbenzylamino]-2,6,6-trimethylbicyclo[3.1.1] heptan-2-ol (2), (1S,2S,3S,5S)-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1] heptan-2-ol (3), and (1R,2R,3R,5R)-3-[(1S)-α-methylbenzylamino]-2,6,6- trimethylbicyclo[3.1.1]heptan-2-ol (4) were synthesized and characterized. It was shown that reduction of the benzylimines by sodium triacetoxyborohydride formed stereoselectively 3β-substituted pinanamines.

Synthesis of 1,2-diamine ligands based on natural monoterpenoids

New nitrogen-containing chiral ligands were synthesized containing terpene fragments of pinane and camphane structure.