105367-62-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(6R)-(-)-4,10-DIMETHYL-7-ISOPROPYL-1,5-DIOXASPIRO[5.5]UNDEC-3-EN-2-ON is used as a synthetic intermediate in the pharmaceutical industry for the synthesis of complex natural products and pharmaceuticals. Its unique chemical properties and reactivity make it a valuable component in the development of new drugs and therapeutic agents.
Used in Organic Chemistry:
In the field of organic chemistry, (6R)-(-)-4,10-DIMETHYL-7-ISOPROPYL-1,5-DIOXASPIRO[5.5]UNDEC-3-EN-2-ON serves as a key intermediate in the synthesis of various complex molecules. Its spirocyclic structure and stereochemistry allow for the creation of novel compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 10458-14-7 (2R,5S)-menthone 
• 105252-83-3 7-isopropyl-10-methyl-1,5-dioxaspiro[5.5]undecane-2,4-dione 
• 75-36-5 acetyl chloride 
• 1694-31-1 tert-butyl acetoacetate 
• 126874-25-7 (6R,7S,10R)-4-Bromomethyl-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-3-en-2-one 

Downstream Products

• 297135-61-6 (6R,7S,10R)-4-[(2S,4S)-5-[2-((2S,6R)-6-Benzyloxymethyl-4,4-dimethoxy-tetrahydro-pyran-2-ylmethyl)-[1,3]dithian-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-5-methyl-hexyl]-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-3-en-2-one 

Relevant academic research and scientific papers

Cycloadditions, 53. New Spirocyclic Chiral Dienes - Synthesis and Diastereoselective Diels-Alder Reactions with N-Phenylmaleimide

Synthesis and diastereoselective Diels-Alder reactions of new spirocyclic chiral dienes are reported.Starting with diketene and (-)-menthone (1), we prepared the diastereomeric diketene-menthone adducts 2 and 3.Further derivatization and olefination afforded four chiral dienes 12-15.Diastereoselective Diels-Alder reactions of these dienes with N-phenylmaleimide (NPM) under high-pressure conditions yielded the corresponding cycloadducts 16-19.Olefination of 6-diethylphosphonomethyl-2,2-dimethyl-1,3-dioxin-4-one 8 with formaldehyde led to unexpected compounds 9-11 resulting from the originally formed olefination product. - Key Words: Dienes, chiral / 1,3-Dioxin-4-ones / (-)-Menthone / Diels-Alder reactions, diastereoselective / Cycloadditions, high-pressure

(6S,7S,10R)- and (6R,7S,10R)-Isopropyl-10-methyl-4-oxo-1,5-dioxaspiroundec-2-enes having an Electron-withdrawing Substituent at the 2-Position: Synthesis and Use in Asymmetric Diels-Alder Reactions

Chiral spirocyclic dioxinones (S)-(6) and (S)-(7) have been synthesized from (-)-menthone and used in Diels-Alder reactions with cyclopentadiene; remarkable diastereofacial selectivity (isopropyl side) and endo preference observed in these reactions have offered a new methodology for asymmetric Diels-Alder reactions.

Note on Mono- and Bisadducts of Diketene to (-)-Menthone

Onium salt and acid catalyzed addition of diketene to (-)-menthone gives improved yields of 2 and 3.Excess of diketene leads to diastereomeric mixtures of compounds 4 and 6 from menthone and menthol, respectively. - Key words: 1,3-Dioxin-4-ones from Ketones