43126-21-2

Usage

Uses

Used in Pharmaceutical Industry:
(2S,5R)-2,7,10,10-tetramethyl-1-oxaspiro[4.5]dec-7-ene is utilized as a potential active pharmaceutical ingredient due to its unique molecular arrangement and chirality, which may offer novel therapeutic effects and selectivity in drug development.
Used in Materials Science:
In the field of materials science, (2S,5R)-2,7,10,10-tetramethyl-1-oxaspiro[4.5]dec-7-ene is employed as a component in the design and synthesis of new materials with specific properties, such as improved stability, reactivity, or selectivity, owing to its intricate spiro structure.
Used in Chemical Research:
(2S,5R)-2,7,10,10-tetramethyl-1-oxaspiro[4.5]dec-7-ene serves as a subject of study in chemical research, where its structure and properties are analyzed to understand its behavior and potential applications in various chemical processes and reactions.

Upstream product

• 57069-87-1 4-(6,6-Dimethyl-2-methylene-cyclohex-3-enyl)-butan-2-ol 
• 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 
• 20013-73-4 2,6,6-trimethylcyclohex-2-en-1-one 
• 113832-38-5 (2R*,5R*)-6,10,10-Trimethyl-1-oxaspiro<4.5>dec-6-en-2-ol 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 446024-10-8 (R)-4-(2,6,6-trimethylcyclohex-1-enyl)butan-2-yl acetate 
• 446293-94-3 C₁₃H₂₄O 
• 160022-97-9 C₁₃H₂₄O 
• 113110-02-4 3-(3-hydroxy-butyl)-2,4,4-trimethyl-cyclohex-2-enol 
• 36431-72-8 2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-ene 
• 113832-27-2 (Z)-2,6,6-Trimethyl-1-<3-(tetrahydro-2-pyranyloxy)-2-propen-1-yl>-2-cyclohexen-1-ol 

Downstream Products

• 65416-59-3 (2RS,5RS)-vitispirane 
• 66965-89-7 (2R*,5S*)-2,6,10,10-Tetramethyl-1-oxaspiro<4.5>dec-6-en 
• 66965-88-6 (2R*,5R*)-2,6,10,10-Tetramethyl-1-oxaspiro<4.5>dec-6-en 

Relevant academic research and scientific papers

(2R,5S)-Theaspirane Identified as the Kairomone for the Banana Weevil, Cosmopolites sordidus, from Attractive Senesced Leaves of the Host Banana, Musa spp.

The principal active component produced by highly attractive senesced host banana leaves, Musa spp., for the banana weevil, Cosmopolites sordidus, is shown by coupled gas chromatography-electroantennography (GC-EAG), coupled GC-mass spectrometry (GC-MS),

PEST ATTRACTANT COMPOSITIONS COMPRISING THEASPIRANE

Described herein is a pest attractant composition comprising theaspirane or an attractive derivative, homologue, isomer or mixture of isomers thereof. Also described is use of the composition for attracting pests and a trap for catching pests comprising t

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.

New methods for the preparation of theaspiranes, megastigmane-5,7,9-trien-4-one and megastigmane-5,8-dien-4-one from γ-pyronene

γ-Pyronene, a terpenic synthon easily available from myrcene, an industrial raw material, is used as an intermediate in the synthesis of theaspiranes and various megastigmane derivatives. These compounds are useful in the preparation of perfumes and aromas. (C) 2000 Elsevier Science Ltd.

Amberlyst-15-catalyzed intramolecular S(N)2' oxaspirocyclization of secondary allylic alcohols. Application to the total synthesis of spirocyclic ethers theaspirane and theaspirone

A variety of substituted 1-oxaspiro[4.4]non-6-ene. 1-oxaspiro[4.5]dec-6- ene, 6-oxaspiro[4.5]dec-1-ene and 1-oxaspiro[5.5]undec-7-ene systems have been prepared by utilizing Amberlyst-15-catalyzed intramolecular S(N)2' oxaspirocyclizations of secondary allylic alcohols under mild reaction conditions in quantitative yields. This oxaspirocyclization was applied to the total synthesis of theaspirane and theaspirone from β-ionone in five steps. (C) 2000 Elsevier Science Ltd.

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.

A NOVEL SELENIUM-MEDIATED SPIROANNELATION: ONE-STEP PREPARATION OF d1-THEASPIRANE FROM α-DIHYDROIONOL

dl-Theaspirane (1) was prepared by the selenium-mediated electrochemical oxidation of α-dihydroionol (2), via a novel selenium-mediated spiroannelation.

AN ELECTROCHEMICAL CHLORINATIVE ENE-TYPE REACTION OF ISOPRENOIDS

The chlorinative ene-type reaction of isoprenoids (12) has been performed by electrolysis in CH2Cl2-H2O-NaCl system.The reaction provides useful allylic chlorides 2 for terpene synthesis in high yields and is affected strikingly by the nature of halide ions and solvents. dl-Theaspirane 21 was prepared from α-dihydroionol via the electrolysis.