188567-99-9

Usage

Uses

Used in Research Applications:
2-Cyclohexen-1-one, 5-(1-methylethenyl)-, (5R)is used as a research reagent for the preparation of ouabagenin, a naturally occurring steroidal glycoside with various biological activities, via anionic cyclization. This application is significant in the field of organic chemistry and pharmaceutical research, as it aids in the synthesis of complex molecules with potential therapeutic properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Cyclohexen-1-one, 5-(1-methylethenyl)-, (5R)is used as a key intermediate in the synthesis of various bioactive compounds, including those with potential applications in drug development. Its unique structure and reactivity make it a valuable building block for creating novel molecules with specific biological targets.
Used in Chemical Synthesis:
2-Cyclohexen-1-one, 5-(1-methylethenyl)-, (5R)is also utilized in chemical synthesis for the production of various specialty chemicals, such as fragrances, dyes, and other compounds with specific applications in the chemical and materials science industries. Its versatility in reactions and ability to form diverse products make it an important compound in the synthesis of specialty chemicals.

Upstream product

• 139561-13-0 (R)-methyl 3-(2,2-dimethoxyethyl)-4-methylpent-4-enoate 
• 731811-36-2 (R)-4-Methyl-3-(2-oxo-ethyl)-pent-4-enoic acid 
• 188568-04-9 (3R)-3-(2,2-dimethoxyethyl)-4-methyl-4-pentenoic acid 
• 872525-75-2 (R)-4-(2,2-Dimethoxy-ethyl)-5-methyl-hex-5-en-2-one 
• 188567-98-8 (R)-3-Isopropenyl-5-oxo-hexanal 

Downstream Products

• 188568-00-5 ((R)-5-Isopropenyl-cyclohex-1-enyloxy)-trimethyl-silane 
• 731811-35-1 (+)-5-isopropenyl-3-methyl-cyclohex-2-enone 
• 859843-12-2 (5R)-2-hydroxymethyl-5-isopropenyl-cyclohex-2-enone 
• 872525-97-8 (R)-4-Isopropenyl-6-oxo-cyclohex-1-enecarbaldehyde 
• 872525-82-1 (4S,4aS,7R,8aR)-4-{(R)-1-Acetoxy-2-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-4a-formyl-2-hydroxy-7-isopropenyl-5-oxo-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid allyl ester 
• 1449386-17-7 C₁₅H₂₀N₂O₄ 
• 1449385-98-1 C₂₁H₃₄N₂O₄Si 

Relevant academic research and scientific papers

Studies towards the total synthesis of ouabagenin

An anionic cyclization strategy developed in our laboratory was used to produce a versatile and convergent synthesis of an advanced tetracyclic intermediate for the construction of ouabagenin and closely related analogs.

Synthesis of (+)- and (-)-isocarvone

The first synthesis of 5-isopropenyl-3-methyl-cyclohex-2-enone, (isocarvone) (2), in enantiomerically pure form is reported. Both enantiomers of 2 can be produced by manipulation of carboxylic acid 5, which is available from R-(-)-carvone (1). These materials provide new chiral building blocks that could be used in total synthesis of natural products and related optically active compounds.

A stereoselective total synthesis of (-)-rishitin

A new synthesis of (-)-rishitin (1) is reported, starting with chiral pool molecules. The crucial step is a stereoselective vinyl radical cyclization, which gives a 10:1 ratio of 21 to 22.