57069-86-0

Usage

Physical state

Colorless liquid

Odor

Strong, sweet floral

Uses

a. Fragrance ingredient in perfumes and personal care products
b. Synthesis of other organic compounds

Safety precautions

a. Can be irritating to the skin
b. Can be irritating to the eyes
c. Can be irritating to the respiratory system

Handling

Should be handled with care and proper safety precautions

InChI:InChI=1/C13H22O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h5-6,11,14H,7-9H2,1-4H3

Upstream product

• 20483-36-7 4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)butan-2-one 
• 14398-35-7 (3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one 
• 79-77-6 (E)-β-ionone 

Downstream Products

• 65416-59-3 (2RS,5SR)-vitispirane 
• 65416-59-3 (2RS,5RS)-vitispirane 

Relevant academic research and scientific papers

Syntheses of theaspirone and vitispirane via palladium(II)-catalyzed oxaspirocyclization

Total syntheses of theaspirone (A and B) and vitispirane (A and B) are described. The key step in the syntheses is the palladium(II)-catalyzed intramolecular oxaspirocyclization of diene alcohol 4 to either vitispirane or the allylic alcohol 9. The outcome of the oxaspirocyclization is very much dependent on the solvent employed. In water-acetic acid (4:1) a 1:1 mixture of the diastereomeric alcohols 9A and 9B was exclusively formed. In water with 8 equiv of a strong non-nucleophilic acid, vitispiranes A and B (1:1) were obtained. An alternative procedure to obtain vitispirane with the use of LiCl and K2CO3 is described. In the latter reaction vitispirane B is formed preferentially. This result is explained by an equilibrium between the two possible π-allyl complexes 5A and 5B, the kinetically favored 5B being transformed into vitispirane 3B before isomerization to 5A occurs.

Palladium-catalyzed oxaspirocyclizations

Palladium-catalyzed oxidation of 1-(3-hydroxyalkyl) and 1-(4- hydroxyalkyl)-1,3-cycloalkadienes results in a stereocontrolled oxaspirocyclization. The reaction proceed via a spirocyclic (π- allyl)palladium intermediate, which is attacked by an acetate or a chloride nucleophile leading to an overall 1,4-addition across the diene. The intermediate (π-allyl) palladium complex was independently prepared and characterized. The stereochemistry of the 1,4-addition can be controlled to give either cis or trans 1,4-addition across the double bonds. The oxaspirocyclization was applied to the total synthesis of theaspirone.