1845-25-6

Basic information

• Product Name: (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone
• Synonyms: (1S,2S,5S)-(-)-2-HYDROXY-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-3-ONE;(1S,2S,5S)-2-HYDROXY-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPTAN-3-ONE;(-)-(1S,2S,5S)-2-HYDROXY-3-PINANONE;(1S,2S,5S)-(-)-2-HYDROXY-3-PINANONE;(1S,2S,5S)-(-)-2-HYDROXYPINAN-3-ONE;Hydroxypinanone; (-)-2a-Hydroxypinocamphone;(1S 2S 5S)-(-)-2-HYDROXYPINAN-3-ONE 99+%
• CAS NO: 1845-25-6
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23
• Product Categories: Chiral Reagents;Asymmetric Synthesis;Bicyclic Monoterpenes;Biochemistry;Synthetic Organic Chemistry;Terpenes;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1845-25-6.mol
• Article Data: 30

Chemical Properties

• Melting Point: 36-38 °C(lit.)
• Boiling Point: 245 °C(lit.)
• Flash Point: 224 °F
• Appearance: /
• Density: 1.059 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00491mmHg at 25°C
• Refractive Index: -33 ° (C=0.5, CHCl3)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate, Methanol
• PKA: 12.93±0.40(Predicted)
• BRN: 3196635
• CAS DataBase Reference: (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone(1845-25-6)
• EPA Substance Registry System: (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone(1845-25-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1845-25-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 1845-25-6 differently. You can refer to the following data:
1. A useful chiral auxillary for synthesis
2. (1S,2S,5S)-(-)-2-Hydroxy-3-pinanone is an essential oil from Hyssopus officinalis L. and Cymbopogon jwarancusa (Jones) Schult.
3. An essential oil from Hyssopus officinalis L. and Cymbopogon jwarancusa (Jones) Schult. It is used in cosmetics.

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 
• 7785-26-4 (-)-α-pinene 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 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 
• 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 
• 176896-75-6 tert-butyl 2-[(E)-((1S,2S,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylidene)amino]acetate 
• 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 
• 125423-98-5 [(1S,2S,5S)-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 [(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-acetic acid (1R,2S,5R)-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 (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 
• 90473-00-0 ethyl 2-((S,2S,5S)-2-hydroxypinan-3-imino)glybioncin C 
• 90473-01-1 (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate 
• 126003-96-1 (1S,2S,5S)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 126003-97-2 (1R,2R,5R)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 18680-27-8 pinanediol 
• 328000-43-7 (1S,2S,5S)-3-(4,5-Diphenyl-1,3-oxazol-2-ylmethylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 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 articles and documents

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

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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.

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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.