1845-25-6

Usage

Uses

Used in Synthesis:
(1S,2S,5S)-(-)-2-Hydroxy-3-pinanone is used as a chiral auxiliary for the synthesis of various compounds, providing a stereoselective approach to the formation of complex molecules.
Used in Cosmetics:
(1S,2S,5S)-(-)-2-Hydroxy-3-pinanone is used as an essential oil in cosmetics for its unique fragrance and potential benefits to the skin.
Used in the Production of Essential Oils:
(1S,2S,5S)-(-)-2-Hydroxy-3-pinanone is found in the essential oils of Hyssopus officinalis L. and Cymbopogon jwarancusa (Jones) Schult., which are used in various applications such as aromatherapy and perfumery.

InChI:InChI=1/C10H16O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-7,12H,4-5H2,1-3H3/t6?,7?,10-/m0/s1

Upstream product

• 7785-70-8 (+)-α-pinene 
• 176896-75-6 tert-butyl 2-[(E)-((1S,2S,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylidene)amino]acetate 
• 329710-76-1 2-(trifluoromethoxy)ethyl trifluoromethanesulphonate 
• 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 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 138175-23-2 (1R,2R,5R)-2,6,6-Trimethyl-3-[(E)-pyridin-2-ylmethylimino]-bicyclo[3.1.1]heptan-2-ol 
• 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 
• 14575-93-0 isopinocamphone 
• 473-62-1 (1S,5R)-2,6,6-Trimethyl-bicyclo[3.1.1]heptan-3-one 
• 80-56-8 Pinene 
• 21803-49-6 (1S,2S,3R,5S)-(+)-pinanediol 
• 18680-27-8 pinanediol 

Downstream Products

• 125423-99-6 [(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid cyclohexyl ester 
• 18680-27-8 pinanediol 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 126003-98-3 (1R,2R,5R)-3-[(1S)-α-methylbenzylimino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 1289376-23-3 (1R,2R,3R,5R)-3-[(1S)-α-methylbenzylamino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 1325620-10-7 C₃₄H₃₆O₂P₂ 
• 1325620-11-8 C₂₃H₂₉O₂P 

Relevant academic research and scientific papers

New optically active cn-palladacycles based on 2α-hydroxypinan-3-one and camphor derivatives

The ligand (-)-2α-hydroxypinan-3-one diphenylmethylimine was synthesized and studied. New dinuclear CN-palladacycles and their mononuclear triphenylphosphine derivatives were obtained. It was shown that ortho-palladation of terpene diphenylmethylimines pr

New unsymmetrical salen-type ligand from enantiomerically pure 2-hydroxypinan-3-one

The reaction of enantiomerically pure (-)-2-hydroxypinan-3-one with ethylenediamine was studied. Depending on the reagent ratio, the reaction can afford either mono- or bis-Schiff's bases. The enantiomerically pure unsymmetrical terpenoid salen-type ligan

Selective oxidation of tertiary-secondary vic-diols to α-hydroxyketones by dioxiranes

Isolated dimethyldioxirane (1a) and methyl(trifluoromethyl)dioxirane (1b) efficiently afford the conversion of bicyclic diols bicyclo [2.2.2]octane-1,2-diol (2) and (+)-pinane-2,3-diol (6), of tricyclic diols adamantane-1,2-diol (3), homoadamantane-3,4-diol (4), and of homopentaprismane-3,4-diol (5) into the corresponding α-hydroxy ketones in high yields and under mild conditions. In the oxidation of (+)-pinane-2,3-diol (6), (-)-2-hydroxy-3-pinanone (11) is obtained in optical yield> 97% with retention of configuration.

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.

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.

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.

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.

METHODS FOR THE SYNTHESIS OF SPHINGOMYELINS AND DIHYDROSPHINGOMYELINS

The present invention includes methods for the synthesis of sphingomyelins and dihydrosphingomyelins. The present invention also includes methods for the synthesis of sphingosines and dihydrosphingosines. The present invention further includes methods for the synthesis of ceramides and dihydroceramides.