82936-58-1

Basic information

• Product Name: Cyclohexene, 1-(1,3-butadiynyl)- (9CI)
• Synonyms: Cyclohexene, 1-(1,3-butadiynyl)- (9CI)
• CAS NO: 82936-58-1
• Molecular Formula: C₁₀H₁₀
• Molecular Weight: 130.1864
• Mol File: 82936-58-1.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclohexene, 1-(1,3-butadiynyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexene, 1-(1,3-butadiynyl)- (9CI)(82936-58-1)
• EPA Substance Registry System: Cyclohexene, 1-(1,3-butadiynyl)- (9CI)(82936-58-1)

Safety Data

• Hazardous Substances Data: 82936-58-1(Hazardous Substances Data)

Upstream product

• 85678-39-3 1-[4-(trimethylsilyl)-1,3-butadiyn-1-yl]cyclohexene 
• 108-94-1 cyclohexanone 
• 931-49-7 1-ethenylcyclohexene 
• 352296-86-7 6-(cyclohex-1-en-1-yl)-2-methylhexa-3,5-diyn-2-ol 
• 13757-08-9 1-(1-hydroxycyclohexyl)-1,3-butadiyne 

Downstream Products

• 1370017-56-3 1-(4-fluorobuta-1,3-diynyl)cyclohex-1-ene 
• 1380540-05-5 C₂₇H₂₂F₄N₂O₂ 
• 74751-57-8 di-cyclohex-1-enyl-octatetrayne 
• 1394290-90-4 1-(6,6,6-trifluorohexa-1,3-diyn-1-yl)cyclohex-1-ene 
• 1314872-22-4 (R)-5-cyclohexenyl-1-cyclohexylpenta-2,4-diyn-1-ol 
• 1314872-09-7 (R)-5-cyclohexenyl-1-phenylpenta-2,4-diyn-1-ol 
• 82936-59-2 1-(1-cyclohexenyl)-1,3-butanedione 
• 1415638-84-4 N-(5-(cyclohex-1-en-1-yl)-1-phenylpenta-2,4-diyn-1-yl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Syntheses of trifluoroethylated unsymmetrical 1,3-diynes by using 1,1-dichloro-2,2,2-trifluoroethane

Copper-mediated reaction of terminal 1,3-diynes with 1,1-dichloro-2,2,2-trifluoroethane (CF3CHCl2) using ethanolamine as ligand gave trifluoroethylated unsymmetrical 1,3-diynes in moderate to good yields. The reaction were carried out under mild conditions, and were easy to operate. Aryl groups with weak electron-withdrawing group or electron-donating group, and alkyl substitutents at terminal 1,3-diynes were tolerated. Synthesis of a trifluoroethylated conjugated triyne by using this method was demonstrated. Further transformation of the trifluoroethylated unsymmetrical 1,3-diyne to provide trifluoroethyl-substituted 1,2,3-triazole and isoxazole as application examples were successfully realized.

Zinc-mediated enantioselective addition of terminal 1,3-diynes to N-arylimines of trifluoropyruvates

A facile and effective enantioselective addition of terminal 1,3-diynes to acyclic α-CF3 ketimine esters has been developed by using zinc/Binol complexes. The reaction works well with a variety of aromatic-, aliphatic- and silyl-substituted diynes, providing the desired products in up to 97% yield and 97% enantiomeric excess.

Enantioselective prophenol-catalyzed addition of 1,3-diynes to aldehydes to generate synthetically versatile building blocks and diyne natural products

A highly enantioselective method for the catalytic addition of terminal 1,3-diynes to aldehydes was developed using our dinuclear zinc ProPhenol (1) system. Furthermore, triphenylphosphine oxide was found to interact synergistically with the catalyst to substantially enhance the chiral recognition. The generality of this catalytic transformation was demonstrated with aryl, α,β-unsaturated and saturated aldehydes, of which the latter were previously limited in alkynyl zinc additions. The chiral diynol products are also versatile building blocks that can be readily elaborated; this was illustrated through highly selective trans-hydrosilylations, which enabled the synthesis of a β-hydroxyketone and enyne. Additionally, the development of this method allowed for the rapid total syntheses of several biologically important diynol-containing natural products.