140709-89-3

Basic information

• Product Name: 2-Cyclohexen-1-one, 2-ethenyl-
• CAS NO: 140709-89-3
• Molecular Formula: C8H10O
• Molecular Weight: 122.167
• Mol File: 140709-89-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-one, 2-ethenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one, 2-ethenyl-(140709-89-3)
• EPA Substance Registry System: 2-Cyclohexen-1-one, 2-ethenyl-(140709-89-3)

Safety Data

• Hazardous Substances Data: 140709-89-3(Hazardous Substances Data)

Upstream product

• 930-68-7 cyclohexenone 
• 50870-61-6 2-bromocyclohex-2-en-1-one 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 141237-72-1 1,4-dioxa-6-formylspiro[4,5]dec-6-ene 
• 70156-98-8 6-bromo-1,4-dioxaspiro[4,5]dec-6-ene 
• 1826-67-1 vinyl magnesium bromide 
• 118949-96-5 2-vinylcyclohex-2-en-1-one ethylene glycol ketal 

Downstream Products

• 124292-44-0 1-methyl-2-vinylcyclohex-2-en-1-ol 
• 96894-91-6 (+)-(3R,4S)-tanshindiol B 
• 97465-70-8 tanshindiol B 
• 96839-30-4 (+)-(3S,4S)-tanshindiol C 
• 96839-30-4 tanshindiol C 
• 96839-30-4 (±)-tanshindiol C 
• 96839-29-1 6-hydroxy-1,6-dimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione 
• 77769-21-2 1,6-dimethyl-8,9-dihydrophenanthro[1,2-b]furan-10,11-dione 
• 568-73-0 Tanshinone I 
• 403694-37-1 3-methoxy-3-methyl-2-vinylcyclohexene 
• 403694-38-2 3-methoxy-2-vinylcyclohexene 
• 503836-82-6 1-phenyl-2-vinylcyclohex-2-en-1-ol 
• 503836-83-7 1-allyl-2-vinylcyclohex-2-en-1-ol 
• 503836-85-9 1-isopropenyl-2-vinylcyclohex-2-en-1-ol 

Relevant articles and documents

Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C

A concise and efficient approach was established for the divergent total synthesis of (±)-tanshindiol B and C and tanshinone I from a ubiquitous ene intermediate in 1-2 steps. This critical intermediate was derived from (±)-tanshinol B, which was synthesized in 50% overall yield over 3 steps using an ultrasound-promoted cycloaddition as a key step. Compared to a previously reported strategy, our approach is more step-economic, thus greatly improving the synthetic efficiency. The bioactivity evaluation indicates that the diol stereochemistry of the tanshidiols has an impact on the EZH2 inhibitory activity.

Heteroatom influence on the π-facial selectivity of Diels-Alder cycloadditions to 1-oxa-4-thia-6-vinylspiro[4.5]dec-6-ene, 3-Methoxy-3-methyl-2-vinylcyclohexene, and 3-methoxy-2-vinylcyclohexene

The facial selectivities of the Diels-Alder cycloadditions of several dienophiles to the title substrates were studied. The observed selectivities are interpreted as a consequence of the relative steric interactions offered by the substituents. The addition of dimethylacetylene dicarboxylate (DMAD) is influenced by the electrostatic repulsion arising from the interaction of an electron pair orbital on the acetal oxygen and the orthogonal π-orbital of the acetylene unit in DMAD in the syn-to-oxygen addition of the latter. This repulsion is offset on coordination of Li+ to the said oxygen electron pair orbital, and the addition thus proceeds syn to oxygen. The enhanced and accelerated syn-to-oxygen addition in lithium perchlorate in nitromethane is interpreted as a consequence of the coordination of Li+ to both the acetal oxygen and a heteroatom in the dienophile that brings them in close proximity to facilitate a reaction. The Li+-oxygen combination, however, also exerts some steric effect that results in reduced syn-to-oxygen addition of dienophiles having large substituents such as N-phenylmaleimide.

Modified stille coupling utilizing α-iodoenones

α-Iodoenones undergo Pd-catalyzed coupling with alkenyl- and aryltributylstannanes providing an efficient route to the corresponding α-substituted enones.