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

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

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

Downstream Products

• 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 
• 120301-52-2 (E)-N-[4-(4-Benzhydryl-piperazin-1-yl)-butyl]-3-naphthalen-1-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.

Enantioselective Synthesis of 3,4-Dihydropyran-2-ones via Phase-Transfer-Catalyzed Addition-Cyclization of Acetylacetone to Cinnamic Thioesters

Herein, we present the first example of synthesis of 3,4-dihydropyran-2-ones from cinnamic thioesters via a stereoselective phase-transfer-catalyzed domino Michael-cyclization reaction with acetylacetone. The reaction proceeded under the catalysis of Cinchona-derived quaternary ammonium phenoxide that, in combination with inorganic bases, provided 3,4-dihydropyran-2-ones in yields of up to 93% and enantioselectivities of up to 88% enantiomeric excess.

Co(iii)-catalyzed: Z -selective oxidative C-H/C-H cross-coupling of alkenes with triisopropylsilylacetylene

A Co(iii)-catalyzed direct oxidative C-H/C-H cross-coupling reaction of acrylamides with triisopropylsilylacetylene is presented. It is applicable to unsubstituted, internal and terminal acrylamides with a broad functionality tolerance. The feasibility of

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.

Synthesis of new N-(arylcyclopropyl)acetamides and N-(arylvinyl)acetamides as conformationally-restricted ligands for melatonin receptors

N-(Arylcyclopropyl)acetamides and N-(arylvinyl)acetamides or methyl ureas have been prepared as constrained analogues of melatonin. The affinity of these new compounds for chicken brain melatonin receptors and recombinant human MT1 and MT2 receptors was evaluated using 2-[ 125I]-iodomelatonin as radioligand. Strict ethylenic or cyclopropyl analogues of the commercialized agonist agomelatine (Valdoxan) were equipotent to agomelatine in binding bioassays. However, the ethylenic analogue was more effective than the cyclopropyl one in the melanophore aggregation bioassay, but was still less potent than the disubstituted 2,7-dimethoxy- naphtalenic compounds.

The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis

Double asymmetric induction has been employed as a tool to optimise pyrazolidinone-derived organocatalysts for the asymmetric iminium ion catalysed Diels-Alder reaction. Mechanistic studies revealed a superior hydrazide catalyst deriving from methanolysis of the chiral pyrazolidinone precursor. This catalyst displays unusually high endo diastereoselectivity and good enantioselectivity with a range of β-arylenals and cyclic dienes at catalyst loadings as low as 1 mol%.

Photoinduced DNA cleavage by anthracene based hydroxamic acids

Two different series of naphthalene and anthracene based hydroxamic acids having amino acid derivatives were synthesized. Single strand DNA cleavage was achieved on irradiation of newly synthesized hydroxamic acids by UV light (≥350 nm). Both reactive oxy

The combination of 4-anilinoquinazoline and cinnamic acid: A novel mode of binding to the epidermal growth factor receptor tyrosine kinase

A novel type of cinnamic acid quinazoline amide derivatives (20-42), which designed the combination between quinazoline as the backbone and various substituted cinnamic acid as the side chain, have been synthesized and their biological activities were evaluated within cytotoxicity assay firstly and then potent EGFR inhibitory activity. Compound 42 demonstrated the most potent inhibitory activity (IC50 = 0.94 μM for EGFR), which could be optimized as a potential EGFR inhibitor in the further study. Docking simulation was performed to position compound 42 into the EGFR active site to determine the probable binding model. Analysis of the binding conformation of 42 in active site displayed compound 42 was stabilized by hydrogen bonding interactions with Lys822, which was different from other derivatives. In the further study, Compounds 43 and 44 had been synthesized and their biological activities were also evaluated, which were the same as that we expected. Compound 43 has demonstrated significant EGFR (IC50 = 0.12 μM) and tumor growth inhibitory activity as a potential anticancer agent.

Design and evaluation of 'Linkerless' hydroxamic acids as selective HDAC8 inhibitors

In this report, we describe new HDAC inhibitors designed to exploit a unique sub-pocket in the HDAC8 active site. These compounds were based on inspection of the available HDAC8 crystal structures bound to various inhibitors, which collectively show that the HDAC8 active site is unusually malleable and can accommodate inhibitor structures that are distinct from the canonical 'zinc binding group-linker-cap group' structures of SAHA, TSA, and similar HDAC inhibitors. Some inhibitors based on this new scaffold are >100-fold selective for HDAC8 over other class I and class II HDACs with IC50 values 1 μM against HDAC8. Furthermore, treatment of human cells with the inhibitors described here shows a unique pattern of hyperacetylated proteins compared with the broad-spectrum HDAC inhibitor TSA.