120681-10-9

Basic information

• Product Name: (E)‐3‐(naphthalen‐1‐yl)acryloyl chloride
• CAS NO: 120681-10-9
• Molecular Weight: 216.667
• Mol File: 120681-10-9.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (E)‐3‐(naphthalen‐1‐yl)acryloyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (E)‐3‐(naphthalen‐1‐yl)acryloyl chloride(120681-10-9)
• EPA Substance Registry System: (E)‐3‐(naphthalen‐1‐yl)acryloyl chloride(120681-10-9)

Safety Data

• Hazardous Substances Data: 120681-10-9(Hazardous Substances Data)

Upstream product

• 66-77-3 1-naphthaldehyde 
• 98978-43-9 (E)-ethyl 3-(naphthalen-1-yl)acrylate 
• 13026-12-5 (E)-3-(naphthalen-1-yl)acrylic acid 

Downstream Products

• 120301-52-2 (E)-N-[4-(4-Benzhydryl-piperazin-1-yl)-butyl]-3-naphthalen-1-yl-acrylamide 
• 85992-25-2 1-chloronaphtho<2,1-b>thiophene-2-carboxoyl chloride 
• 56252-02-9 2-hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-1-one 
• 65874-44-4 2-hydroxy-9-(4'-methoxyphenyl)-1H-phenalen-1-one 
• 65874-43-3 9-(4-methoxyphenyl)-1H-phenalen-1-one 
• 548-39-0 Perinaphthenon 
• 1333163-20-4 (E)-N-(4-(3-chlorophenylamino)quinazolin-6-yl)-3-(naphthalen-4-yl)acrylamide 

Relevant articles and documents

Non-thiol farnesyltransferase inhibitors: utilization of an aryl binding site by 5-arylacryloylaminobenzophenones.

We recently described a novel aryl binding site of farnesyltransferase. The 2-naphthylacryloyl residue was developed as an appropriate substituent for our benzophenone-based AAX-peptidomimetic capable of occupying this binding site, resulting in a non-thiol farnesyltransferase inhibitor with nanomolar activity. The activity of this inhibitor is readily explained on the basis of docking studies which show the 2-naphthyl residue fitting into the aryl binding site.

Modular Cyclopentenone Synthesis through the Catalytic Molecular Shuffling of Unsaturated Acid Chlorides and Alkynes

We describe a general strategy for the intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis. Overall, this reaction is achieved via a molecular shuffling process involving an alkyne, an α,β-unsaturated acid chloride, which serves as both the alkene and carbon monoxide source, and a hydrosilane to create three new C-C bonds. This new carbon monoxide-free pathway delivers the products with excellent yields. Furthermore, the regioselectivity is complementary to conventional methods for cyclopentenone synthesis. In addition, a set of regio- and chemodivergent reactions are presented to emphasize the synthetic potential of this novel strategy.

Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer

Concise total syntheses of the natural phytoalexins 2-hydroxy-8-(4-hydroxyphenyl)phenalen-1-one (1), 2-hydroxy-8-(3,4-dihydroxyphenyl)phenalen-1-one (2), and hydroxyanigorufone (4), together with regioisomer 3 are accomplished in 11 or 12 steps. The synthetic strategy features a Friedel-Crafts acylation to construct the 1H-phenalen-1-one tricyclic core followed by a Suzuki cross-coupling to obtain the target compounds.