123376-75-0

Basic information

• Product Name: (S*)-3-((R*)-but-3-en-2-yl)cyclohexan-1-one
• CAS NO: 123376-75-0
• Molecular Weight: 152.236
• Mol File: 123376-75-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S*)-3-((R*)-but-3-en-2-yl)cyclohexan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S*)-3-((R*)-but-3-en-2-yl)cyclohexan-1-one(123376-75-0)
• EPA Substance Registry System: (S*)-3-((R*)-but-3-en-2-yl)cyclohexan-1-one(123376-75-0)

Safety Data

• Hazardous Substances Data: 123376-75-0(Hazardous Substances Data)

Upstream product

• 7515-62-0 (E)-5-bromo-2-pentene 
• 930-68-7 cyclohexenone 
• 123376-82-9 ((E)-But-2-enyl)-ethoxy-dimethyl-silane 
• 123376-81-8 ((Z)-But-2-enyl)-ethoxy-dimethyl-silane 
• 123376-83-0 ((Z)-But-2-enyl)-isopropoxy-dimethyl-silane 
• 91034-74-1 (E)-but-2-en-1-yl(methyl)diphenylsilane 
• 91034-75-2 (Z)-but-2-en-1-yl(methyl)diphenylsilane 
• 17486-12-3 (E)-but-2-en-1-yltrimethylsilane 
• 17486-13-4 (Z)-crotyltrimethylsilane 
• 165825-70-7 (E)-methyl 3-oxo-2-diazo-7-nonanoate 
• 104933-86-0 (1R*,6R*,7R*)-methyl 2-oxo-7-exo-methylbicyclo<4.1.0>heptane-1-carboxylate 
• 104933-84-8 (E)-methyl 3-oxo-7-nonenoate 

Downstream Products

• 123376-85-2 (R)-4-((R)-1-Methyl-allyl)-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 123376-85-2 (R)-4-((S)-1-Methyl-allyl)-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 123376-87-4 (R)-2-Methanesulfonyloxy-4-((S)-1-methyl-allyl)-cyclohexanecarboxylic acid methyl ester 
• 73484-31-8 (S)-4-((R)-2-Chlorocarbonyl-1-methyl-ethyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 72457-75-1 3-(methyl-4-carboxyl-3-cyclohexenyl)butanoic acid 
• 123376-90-9 Methanesulfonic acid (R)-2-methyl-5-((S)-1-methyl-allyl)-cyclohexyl ester 
• 123376-91-0 Methanesulfonic acid (R)-5-((R)-2-hydroxy-1-methyl-ethyl)-2-methyl-cyclohexyl ester 
• 123393-62-4 (R)-2-Hydroxy-4-((S)-1-methyl-allyl)-cyclohexanecarboxylic acid methyl ester 
• 123376-79-4 (S)-4-((R)-1-Methyl-allyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 123376-89-6 (S)-2-Methyl-5-((R)-1-methyl-allyl)-cyclohexanol 
• 70518-81-9 RR-p-Menth-1-en-9-ol 
• 16981-74-1 (+/-)-erythro-juvabione 
• 123376-87-4 (R)-2-Methanesulfonyloxy-4-((R)-1-methyl-allyl)-cyclohexanecarboxylic acid methyl ester 
• 73484-31-8 (S)-4-((S)-2-Chlorocarbonyl-1-methyl-ethyl)-cyclohex-1-enecarboxylic acid methyl ester 

Relevant articles and documents

Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones

A method for the site-selective and diastereoselective conjugate addition of boron-stabilized allylic nucleophiles to α,β-unsaturated ketones is disclosed. Transformations involve easily prepared γ,γ-disubstituted allyldiboron reagents and proceed in the presence of a fluoride activator at 80 °C. Reactions proceed with a wide variety of enones and allyldiboron reagents efficiently to deliver ketone products that contain otherwise difficult-to-access vicinal β-tertiary and γ-quaternary carbon stereogenic centers and an alkenylboron moiety. The utility of the method is highlighted by several transformations, including cross-coupling and carbocyclizations.

EFFICIENT STEREOSELECTIVE SYNTHESIS OF BOTH (+/-)-JUVABIONE AND (+/-)-EPI-JUVABIONE BY NEW EXTRACYCLIC STEREOCONTROL METHODOLOGY

The Hosomi-Sakurai reactions of E- and Z-crotylsilanes with cyclohexenone at -78 degC showed respectively high erythro and relatively low threo selectivities, modification of the silyl substituents giving a variable effect.In the reaction with Z-alkoxycrotylsilanes, the threo selectivity could be improved by the utilization of the kinetic difference between the diastereomeric products 4 and 5 to the secondary cyclization.Starting from 4 and 5 thus obtained, the syntheses of both (+/-)-juvabione and (+/-)-epi-juvabione have been respectively achieved in a concise way.