76152-65-3

Basic information

• Product Name: (R)-(+)-3-ethylcyclohexene
• Synonyms: (R)-(+)-3-ethylcyclohexene
• CAS NO: 76152-65-3
• Molecular Weight: 110.199
• Mol File: 76152-65-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (R)-(+)-3-ethylcyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-3-ethylcyclohexene(76152-65-3)
• EPA Substance Registry System: (R)-(+)-3-ethylcyclohexene(76152-65-3)

Safety Data

• Hazardous Substances Data: 76152-65-3(Hazardous Substances Data)

Upstream product

• 5614-35-7 3-phenoxycyclohexene 
• 925-90-6 ethylmagnesium bromide 
• 68735-62-6 cyclohexen-1-en-3-yl diethyl phosphate 
• 822-67-3 Cyclohex-2-enol 
• 12109-84-1 ethylzirconocene chloride 
• 2441-97-6 3-chloro-cyclohexene 
• 1521-51-3 rac-3-bromocyclohexene 
• 95674-80-9 (1R,1'R)-(+)-1-(2-cyclohexenyl)-1-ethanol 

Downstream Products

• 84275-94-5 (+)-(1S,2R)-2-ethylcyclohexanol 
• 89886-26-0 (-) Trans 2-ethyl cyclohexanol 
• 87759-25-9 (1S,3R)-3-ethyl-cyclohexanol 
• 87759-24-8 trans-1-Aethyl-cyclohexanol-⁽³⁾ 

Relevant articles and documents

Mechanistic Studies on a Cu-Catalyzed Asymmetric Allylic Alkylation with Cyclic Racemic Starting Materials

Mechanistic studies on Cu-catalyzed asymmetric additions of alkylzirconocene nucleophiles to racemic allylic halide electrophiles were conducted using a combination of isotopic labeling, NMR spectroscopy, kinetic modeling, structure-activity relationships, and new reaction development. Kinetic and dynamic NMR spectroscopic studies provided insight into the oligomeric Cu-ligand complexes, which evolve during the course of the reaction to become faster and more highly enantioselective. The Cu-counterions play a role in both selecting different pathways and in racemizing the starting material via formation of an allyl iodide intermediate. We quantify the rate of Cu-catalyzed allyl iodide isomerization and identify a series of conditions under which the formation and racemization of the allyl iodide occurs. We developed reaction conditions where racemic allylic phosphates are suitable substrates using new phosphoramidite ligand D. D also allows highly enantioselective addition to racemic seven-membered-ring allyl chlorides for the first time.1H and2H NMR spectroscopy experiments on reactions using allylic phosphates showed the importance of allyl chloride intermediates, which form either by the action of TMSCl or from an adventitious chloride source. Overall these studies support a mechanism where complex oligomeric catalysts both racemize the starting material and select one enantiomer for a highly enantioselective reaction. It is anticipated that this work will enable extension of copper-catalyzed asymmetric reactions and provide understanding on how to develop dynamic kinetic asymmetric transformations more broadly.

Chiral Synthesis via Organoboranes. Part 32. Synthesis of B-(Cycloalk-2-enyl)-diisopinocampheylboranes of High Enantiomeric Purity via the Asymmetric Hydroboration of Cycloalka-1,3-dienes. Successful Asymmetric Allylborations of Aldehydes with B-(Cycloalk-2-enyl)diisopinocampheylboranes

The hydroboration of cycloalka-1,3-dienes (CnH2n-4, n = 6, 7 and 8) with diisopinocampheylborane (dIpc2BH or lIpc2BH) at -25 deg C provides highly enantiomerically pure B-(cycloalk-2-enyl)diisopinocampheylboranes, l or dIpc2BCnH2n-3 (>/= 93percent ee).Surprisingly, these allylic borane derivatives retain their stereochemical integrity at -25 deg C although such compounds are capable of undergoing racemization through rapid allylic rearrangements.Furthermore, the B-(cycloalk-2-enyl)diisopinocampheylboranes achieve allylborations of aldehydes at -78 deg C and afford 1-(cycloalk-2-enyl)alkan-1-ols in 90-95percent ee and 100percent syn-diastereoselectivity.