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

• 7785-26-4 (-)-α-pinene 
• 7785-70-8 (+)-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

• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 1013027-63-8 (1R,2R,3R,5R)-3-(benzylamino)-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

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 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.