478166-26-6

Basic information

• Product Name: Cyclohexene, 1-(1E)-1-buten-3-ynyl-
• CAS NO: 478166-26-6
• Molecular Formula: C10H12
• Molecular Weight: 132.205
• Mol File: 478166-26-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Cyclohexene, 1-(1E)-1-buten-3-ynyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexene, 1-(1E)-1-buten-3-ynyl-(478166-26-6)
• EPA Substance Registry System: Cyclohexene, 1-(1E)-1-buten-3-ynyl-(478166-26-6)

Safety Data

• Hazardous Substances Data: 478166-26-6(Hazardous Substances Data)

Upstream product

• 18243-59-9 (2-bromoethynyl)trimethylsilane 
• 62072-23-5 ((E)-2-Cyclohex-1-enyl-vinyl)-dicyclohexyl-borane 
• 478166-21-1 ((E)-2-Cyclohex-1-enyl-vinyl)-bis-(1,2-dimethyl-propyl)-borane 

Downstream Products

• 1260102-41-7 C₁₇H₁₆O 
• 1356478-41-5 (E)-1-(cyclohex-1-en-1-yl)dec-1-ene-3,5-diyne 
• 1356478-27-7 (1E,7E)-1,8-di(cyclohex-1-en-1-yl)octa-1,7-diene-3,5-diyne 
• 1562381-56-9 (E)-N-(4-cyclohexenylbut-3-en-1-ynyl)-N,4-dimethylbenzenesulfonamide 

Relevant articles and documents

One-pot synthesis of 1-arylmethyl-4-[(E)-alk-1-enyl]-1H-1,2,3-triazoles via a cross-coupling/click reaction sequence

1-Arylmethyl-4-[(E)-alk-1-enyl]-1H-1,2,3-triazoles have been synthesized from terminal conjugated (E)-enynes, prepared by copper-mediated cross-coupling reaction of (E)-alk-1-enyldisiamylboranes with (trimethylsilyl)ethynyl bromide, benzyl bromides and sodium azide in a one-pot fashion. In this cross-coupling/click reaction sequence, the copper precursor Cu(acac) 2 can serve as a tandem catalyst.

One-pot synthesis of conjugated (E)-enynones via two types of cross-coupling reaction

(Trimethylsilyl)ethynyl bromide can be easily transformed into conjugated (E)-enynones, whose skeleton consists of consecutive carbonyl, ethynyl, and (E)-ethenyl units, via a one-pot multicomponent Suzuki-type reaction-Sonogashira reaction sequence. Thus,

Stereoselective syntheses of (E)- and (Z)-1-arylalk-3-en-1-ynes and (E,E)-, (Z,E)-, (E,Z)-, and (Z,Z)-alka-1,5-dien-3-ynes via a one-pot multicomponent coupling reaction

Both 1-arylalk-3-en-1-ynes and alka-1,5-dien-3-ynes have been synthesized under extremely mild reaction conditions in good to high yields via a sequential Suzuki-type and Sonogashira reaction in a one-pot manner. Thus, the protocol involves Cu-mediated cross-coupling reaction of (E)- or (Z)- alkenyldisiamylborane with (trimethylsilyl)ethynyl bromide in the presence of 1M NaOMe and Pd/Cu-catalyzed cross-coupling reaction with aryl or alkenyl iodide in the presence of aqueous n-Bu4NOH. The reaction with aryl iodide is tolerant of a wide variety of functional groups on the aromatic ring and leads to the stereoselective formation of (E)- and (Z)-1-arylalk-3-en-1-ynes. In addition, the reactions with (E)- and (Z)-1-iodoalk-1-enes have accomplished the construction of all possible combinations of geometrical isomers, (E,E)-, (Z,E)-, (E,Z)-, and (Z,Z)-alka-1,5-dien-3-ynes. Georg Thieme Verlag Stuttgart.