66965-89-7

Basic information

• Product Name: (2S,5R)-2,7,10,10-tetramethyl-1-oxaspiro[4.5]dec-7-ene
• Synonyms: (2R,5S)-2,6,10,10-Tetramethyl-1-oxaspiro[4.5]dec-6-ene; 1-Oxaspiro(4.5)dec-6-ene, 2,6,10,10-tetramethyl-, (2R,5S)-rel-; 1-oxaspiro[4.5]dec-6-ene, 2,6,10,10-tetramethyl-, (2R,5S)-
• CAS NO: 66965-89-7
• Molecular Formula: C₁₃H₂₂O
• Molecular Weight: 194.3132
• Mol File: 66965-89-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 254.1°C at 760 mmHg
• Flash Point: 103.8°C
• Density: 0.94g/cm³
• Vapor Pressure: 0.0281mmHg at 25°C
• Refractive Index: 1.488
• CAS DataBase Reference: (2S,5R)-2,7,10,10-tetramethyl-1-oxaspiro[4.5]dec-7-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-2,7,10,10-tetramethyl-1-oxaspiro[4.5]dec-7-ene(66965-89-7)
• EPA Substance Registry System: (2S,5R)-2,7,10,10-tetramethyl-1-oxaspiro[4.5]dec-7-ene(66965-89-7)

Safety Data

• Hazardous Substances Data: 66965-89-7(Hazardous Substances Data)

Upstream product

• 446293-91-0 4-(2,6,6-trimethyl-cyclohex-1-enyl)-butan-2-ol 
• 65017-80-3 (Z)-1-(3-Hydroxy-1-butenyl)-2,6,6-trimethyl-2-cyclohexen-1-ol 
• 854912-94-0 1-(3-Hydroxybutyl)-2,6,6-trimethyl-2-cyclohexen-1-ol 
• 61693-40-1 (2,6,6-trimethylcyclohex-2-enylidene)butan-2-ol 
• 79-77-6 (E)-β-ionone 
• 41641-11-6 2,6,6-trimethyl-1-hydroxy-1-[3-hydroxy-but-1-ynyl]-cyclohex-2-ene 
• 20013-73-4 2,6,6-trimethylcyclohex-2-en-1-one 
• 113832-58-9 (E)-1-<2-(Cyclohexylimino)ethyl>-2,6,6-trimethyl-2-cyclohexen-1-ol 
• 113832-27-2 (Z)-2,6,6-Trimethyl-1-<3-(tetrahydro-2-pyranyloxy)-2-propen-1-yl>-2-cyclohexen-1-ol 
• 113832-38-5 (2R*,5R*)-6,10,10-Trimethyl-1-oxaspiro<4.5>dec-6-en-2-ol 
• 36431-72-8 2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-ene 

Relevant articles and documents

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.

Structure-Odor Correlation, VII. - Synthesis and Olfactive Properties of Theaspirane Analogues

The spirodihydrofurans 8-12 were prepared by addition of the respective alkynols to the ketone 20 (-->21-25), Lindlar hydrogenation (-->26-30), and cyclization. - The saturated derivatives 1-6 were available either by hydrogenation (8-10-->1,2,4) or via the lactol 47 and its reaction to the diols 31-36.Addition of the ethyl acetate anion to 20 (-->71), reduction (71-->73), and cyclization yielded the spirooxetane 13. - From the ynediols 76 and 77, Lindlar hydrogenation (-->78,79), cyclization (-->80,81), and further hydrogenation led to the spirotetrahydropyranes 16and 17. - Key compound for the synthesis of the ketone 18 was the geranic acid derivative 94, which could be obtained in two different ways.Cyclization of 94 to the diester 92 and Dieckmann condensation of 92 under simultaneous methylation (-->99) led to 18.The diastereoisomers 18a and b could be assigned after reduction of 18 to the separable alcohols 19a-c. - The olfactive properties (strength and quality) of the theaspirane analogues are determined by the conformational flexibility of the respective molecule.Thus, the almost rigid 13 has a very strong camphoraceous-herbaceous odor.Augmenting flexibility, particularly by increasing of the ring size (-->1,-->16), but also by alkyl substitution at C-2, results in remarkably weaker, woody-flowery notes.

Vitispiranes, important constituents of vanilla aroma

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