35671-18-2

Usage

Uses

Used in Organic Synthesis:
(1alpha,3alpha,5alpha,7alpha)-3,8,8-trimethyl-4-oxatricyclo[5.1.0.03,5]octane is utilized as a building block in organic synthesis for the assembly of more complex molecules. Its unique structure and functional groups facilitate the synthesis of a variety of organic compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (1alpha,3alpha,5alpha,7alpha)-3,8,8-trimethyl-4-oxatricyclo[5.1.0.03,5]octane serves as an important intermediate for the production of pharmaceuticals. Its distinctive molecular architecture and functional groups make it a key component in the development of new drugs.
Used in Fragrance Industry:
(1alpha,3alpha,5alpha,7alpha)-3,8,8-trimethyl-4-oxatricyclo[5.1.0.03,5]octane is also employed in the fragrance industry, where its unique molecular structure contributes to the creation of novel and complex scents.
Used in Other Organic Compounds Production:
Beyond its applications in organic synthesis, medicinal chemistry, and the fragrance industry, (1alpha,3alpha,5alpha,7alpha)-3,8,8-trimethyl-4-oxatricyclo[5.1.0.03,5]octane is used as a versatile intermediate for the production of a wide range of other organic compounds, highlighting its importance in the chemical industry.

InChI:InChI=1S/C12H20O/c1-9(2)11(4)6-8-10(3,13-8)7-12(9,11)5/h8H,6-7H2,1-5H3/t8-,10+,11-,12+/m1/s1

Upstream product

• 498-15-7 Δ³-carene 
• 498-15-7 (+)-Δ³-carene 
• 13466-78-9 3-carene 
• 20296-50-8 δ-3-carene 

Downstream Products

• 10395-46-7 3β,4α-dihydroxy-3-carane 
• 85392-33-2 Bis(3-hydroxy-4-caranyl) suldide 
• 2517-19-3 3-caren-10-ol 
• 3479-89-8 3,7,7-trimethyl-cyclohepta-1,3,5-triene 
• 86361-47-9 cara-3⁽¹⁰⁾,4-diene 
• 13466-78-9 3-carene 
• 13124-67-9 3,6,6-trimethylbicyclo<3.1.0>hexane-3-carboxaldehyde 
• 4176-01-6 trans-4-caranone 
• 99-87-6 4-methylisopropylbenzene 
• 4176-01-6 cis-carane-4-one 
• 1753-35-1 3⁽¹⁰⁾-caren-4-ol 
• 13124-72-6 3,3,6-trimethylbicyclo<3.1.0>hex-3-ylmethanol 
• 41043-92-9 3,3,6-trimethylcycloheptanone 
• 93905-76-1 4-caren-3-ol 

Relevant academic research and scientific papers

Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions - Synthesis of halohydrins and epoxides

β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br+ and I+ ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-halocarbonyl compounds.

Epoxidation of olefins by β-bromoalkoxydimethylsulfonium ylides

Olefins can be converted to their respective epoxides in a one-pot procedure by dissolving the olefin in anhydrous DMSO, adding NBS to the reaction mixture to generate a β-bromoalkoxydimethylsulfonium ylide, and then adding DBU to the reaction mixture. A large variety of alkenes were successfully epoxi-dized with yields largely dependent on the structure of the alkene. Most importantly, the facial selectivity of this one-pot process is the opposite of that observed when using traditional epoxidizing reagents. Electron-poor alkenes are not epoxidized under these conditions.

Diastereoselective epoxidation of olefins by organo sulfonic peracids, II

We have investigated the behaviour of sulfonic peracids 2 in situ generated towards olefins 7a, 7b, 9, 11, 14, 16, 18, allylic acid and homoallylic alcohols 20, 22, 24, 26, 28, 30, 33 and α,β-unsaturated ketones 35, 37, 39. Generally, the epoxidation proceeds in a peracid-like manner with greater diastereoselectivity than those by common oxidants. In particular, the epoxidation of Δ4 3-ketosteroids 39a-i led to 4α,5α-epoxides 40a-i with remarkable high de-values. Enhanced α-selectivity was also found in the epoxidation of cholesterol 28b. Due to the mild reaction conditions, even acid sensitive epoxides 8a, 8b, 10, 12, 13, 15, 17, 19 were obtained in good yields.

A NEW PARADIGM FOR ALKENE EPOXIDATION. ACTIVATION OF HYDROGEN PEROXIDE BY ORGANOPHOSPHORUS ELECTROPHILES

Diphenylphosphinic anhydride and certain other organophosphorus electrophiles mediate the high-yield conversion of alkenes to epoxides by hydrogen peroxide in buffered aqueous tetrahydrofuran.

Synthesis of naturally-occurring (-)-Δ9(12)-Capnellene and its antipode: An application of the photo-induced vinylcyclopropane-cyclopentene rearrangement

Abundantly available (+)-Δ3-Carene, 1 has been transformed into enantiomerically pure key intermediates viz. the enones (-)-7 and (+)-7, thus constituting a formal synthesis of both the enantiomers of Δ9(12)-Capnellene.