853065-37-9

Basic information

• Product Name: 2-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)quinoline
• Synonyms: 2-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)quinoline
• CAS NO: 853065-37-9
• Molecular Weight: 257.335
• Mol File: 853065-37-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)quinoline(853065-37-9)
• EPA Substance Registry System: 2-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)quinoline(853065-37-9)

Safety Data

• Hazardous Substances Data: 853065-37-9(Hazardous Substances Data)

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 91-63-4 2-methylquinoline 
• 104-55-2 3-phenyl-propenal 
• 1613-37-2 Quinoline N-oxide 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 91-22-5 quinoline 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 137845-37-5 4-methyl-N-(3-phenylallylidene)benzenesulfonamide 

Downstream Products

• 5426-20-0 2-(4-phenylbutyl)quinoline 

Relevant articles and documents

Nematocidal and trichomonacidal activities of 2-substituted quinolines

Several quinolines were synthesized and evaluated in vitro and in vivo against the nematodes Caenorhabditis elegans, Heligmosomoides polygyrus and the protozoa Trichomonas vaginalis. If some of them have shown in vitro nematocide activity (at 10 μM), however, their trichomonacidal activity reached 50% reduction at only 100 μM. The in vivo activity on Trichinella spiralis model was evaluated for some of the most in vitro active quinolines.

C2-Alkenylation of N-heteroaromatic compounds: Via Br?nsted acid catalysis

Substituted heteroaromatic compounds, especially those based on pyridine, hold a privileged position within drug discovery and medicinal chemistry. However, functionalisation of the C2 position of 6-membered heteroarenes is challenging because of (a) the difficulties of installing a halogen at this site and (b) the instability of C2 heteroaryl-metal reagents. Here we show that C2-alkenylated heteroaromatics can be accessed by simple Br?nsted acid catalysed union of diverse heteroarene N-oxides with alkenes. The approach is notable because (a) it is operationally simple, (b) the Br?nsted acid catalyst is cheap, non-toxic and sustainable, (c) the N-oxide activator disappears during the reaction, and (d) water is the sole stoichiometric byproduct of the process. The new protocol offers orthogonal functional group tolerance to metal-catalysed methods and can be integrated easily into synthetic sequences to provide polyfunctionalised targets. In broader terms, this study demonstrates how classical organic reactivity can still be used to provide solutions to contemporary synthetic challenges that might otherwise be approached using transition metal catalysis.

Cobalt-catalyzed direct alkenylation of 2-methylquinolines with aldehydes via C(sp3)-H functionalization in water

The direct C(sp3)-H alkenylation of 2-methylquinolines with aldehydes as a simple methodology to afford 2-alkenylated quinolines is reported. In the presence of catalytic CoCl2 in water, the economically and ecologically sound transformation is proposed to proceed via the direct benzylic addition to the aldehyde followed by an elimination step to provide 2-alkenylated quinolines in good to excellent yield of up to 95%. Georg Thieme Verlag Stuttgart New York.