24047-72-1

Basic information

• Product Name: (1R,2R,5R)-(+)-2-Hydroxy-3-pinanone
• Synonyms: (1R,2R,5R)-(+)-2-HYDROXY-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-3-ONE;(1R,2R,5R)-2-HYDROXY-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPTAN-3-ONE;(+)-(1R,2R,5R)-2-HYDROXY-3-PINANONE;(1R,2R,5R)-(+)-2-HYDROXY-3-PINANONE;(+)-2-Hydroxy-3-pinanone;(1R，2R，5R)-2-Hydroxy-3-pinnone;(1R,2R,5R)-
• CAS NO: 24047-72-1
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23
• Product Categories: API intermediates;Chiral Reagents;Asymmetric Synthesis;Bicyclic Monoterpenes;Biochemistry;Synthetic Organic Chemistry;Terpenes;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 24047-72-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 37-39 °C(lit.)
• Boiling Point: 245 °C(lit.)
• Flash Point: 224 °F
• Appearance: White crystalline solid
• 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: Acetone (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (S
• PKA: 12.93±0.40(Predicted)
• BRN: 2249018
• CAS DataBase Reference: (1R,2R,5R)-(+)-2-Hydroxy-3-pinanone(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,5R)-(+)-2-Hydroxy-3-pinanone(24047-72-1)
• EPA Substance Registry System: (1R,2R,5R)-(+)-2-Hydroxy-3-pinanone(24047-72-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 24047-72-1(Hazardous Substances Data)

Usage

Chemical Properties

(1R,2R,5R)-(+)-2-Hydroxy-3-pinanone is white Crystalline Solid

Uses

Different sources of media describe the Uses of 24047-72-1 differently. You can refer to the following data:
1. (1R,2R,5R)-(+)-2-Hydroxy-3-pinanone is a useful chiral auxillary for synthesis
2. An essential oil from Hyssopus officinalis L. and Cymbopogon jwarancusa (Jones) Schult.

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-/m1/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 
• 80-56-8 rac-α-pinene 

Downstream Products

• 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 
• 90473-01-1 (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate 

Relevant articles and documents

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.