65416-59-3

Usage

Uses

Used in Fragrance Industry:
1-Oxaspiro4.5dec-7-ene, 2,10,10-trimethyl-6-methyleneis used as a fragrance ingredient for its characteristic odor, contributing to the scent profiles of various consumer products such as perfumes, colognes, and air fresheners.
Used in Cosmetics and Personal Care Products Industry:
In addition to its application in fragrances, 1-Oxaspiro4.5dec-7-ene, 2,10,10-trimethyl-6-methyleneis also utilized in the manufacturing of cosmetics and personal care products, enhancing their sensory appeal and consumer experience.
Safety Precautions:
It is crucial to handle 1-Oxaspiro4.5dec-7-ene, 2,10,10-trimethyl-6-methylenewith care due to its potential to cause irritation to the skin, eyes, and respiratory system. Proper safety measures should be taken during its use and handling to minimize any adverse effects.

InChI:InChI=1/C13H20O/c1-10-6-5-8-12(3,4)13(10)9-7-11(2)14-13/h5-6,11H,1,7-9H2,2-4H3

Upstream product

• 78830-90-7 6,6-dimethyl-2-methylene-1-(3-oxobutyl)-3-cyclohexen-1-ol 
• 57069-86-0 7,8-dihydro-3,4-dehydro-β-ionol 
• 14398-35-7 (3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one 
• 78830-89-4 6,6-dimethyl-2-methylene-1-(3-oxo-1-butenyl)-3-cyclohexen-1-ol 
• 39763-31-0 (±)-(3E)-4-[1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one 
• 78830-92-9 (6RS,9SR)-1-(3-hydroxybutyl)-6,6-dimethyl-2-methylene-3-cyclohexen-1-ol 
• 66965-88-6 (2R*,5R*)-2,6,10,10-Tetramethyl-1-oxaspiro<4.5>dec-6-en 
• 36431-72-8 2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-ene 
• 23526-45-6 6,9-dihydroxymegastigma-4,7-dien-3-one 

Relevant academic research and scientific papers

Elucidation of the regio- and chemoselectivity of enzymatic allylic oxidations with Pleurotus sapidus - Conversion of selected spirocyclic terpenoids and computational analysis

Allylic oxidations of olefins to enones allow the efficient synthesis of value-added products from simple olefinic precursors like terpenes or terpenoids. Biocatalytic variants have a large potential for industrial applications, particularly in the pharmaceutical and food industry. Herein we report efficient biocatalytic allylic oxidations of spirocyclic terpenoids by a lyophilisate of the edible fungus Pleurotus sapidus. This ''mushroom catalysis'' is operationally simple and allows the conversion of various unsaturated spirocyclic terpenoids. A number of new spirocyclic enones have thus been obtained with good regio- and chemoselectivity and chiral separation protocols for enantiomeric mixtures have been developed. The oxidations follow a radical mechanism and the regioselectivity of the reaction is mainly determined by bond-dissociation energies of the available allylic CH-bonds and steric accessibility of the oxidation site.

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.

A New Route to Vitispiranes

Diastereoisomeric vitispiranes have been synthesized from 2,6,6-trimethyl-1-(3-oxo-1-butenyl)-1,3-cyclohexadiene by five-step reactions including photooxygenation.

New Syntheses of Edulans and Theaspiranes from α-Inone

New syntheses of edulans and theaspiranes are described.The key step involves the cyclization of 4-(2',6',6'-trimethyl-2'-hydroxy-3'-cyclohexen-1'-yl)-butan-2-ol (7) and 4-(2',6',6'-trimethyl-1',2'-dihydroxy-3'-cyclohexen-1'-yl)-butan-2-ol (8) derived from α-ionone.The diol (7) and triol (8) were cyclized with acetic acid into the corresponding tetrahydropyran derivatives ; the latter two compounds were dehydrated to edulan I and II (13a, 13b).On treatment with tosyl chloride in pyridine, however, triol (8) gave spiro-compounds (11a, 11b and 12); (11a and 11b) were easily converted to cis- and trans-theaspirone by oxidation and 5,6-erythro-6-hydroxy-dihydrotheaspiranes (15a and 15b) by reduction.