20883-90-3

Upstream product

• 67-56-1 methanol 
• 49711-14-0 (E)-3-(naphthalen-2-yl)acrylic acid 
• 60413-07-2 4-[2]naphthylazo-morpholine 
• 292638-85-8 acrylic acid methyl ester 
• 573-57-9 1,4-dihydronaphthalene-1,4-epoxide 
• 922-67-8 propynoic acid methyl ester 
• 66-99-9 β-naphthaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 450-58-8 2-naphthyldiazonium tetrafluoroborate 
• 79-20-9 acetic acid methyl ester 
• 612-55-5 2-iodonaphthalene 
• 580-13-2 2-bromonaphthalene 
• 1942-46-7 5-decyne 
• 32316-92-0 naphthalene-2-boronic acid 

Downstream Products

• 170166-53-7 methyl 2'-naphthoylformate 
• 122-97-4 3-Phenyl-1-propanol 

Relevant academic research and scientific papers

(2-Arylethenyl)-1,3,5-triazin-2-amines as a novel histamine H4 receptor ligands

Within the constantly growing number of histamine H4 (H4R) receptor ligands there is a large group of azine derivatives. A series of novel compounds in the group of 4-methylpiperazine-1,3,5-triazine-2-amines were designed and obtained. Considered structures were modified at the triazine 6-position by introduction of variously substituted arylethenyl moieties. Their affinities to histamine H4 receptors were evaluated in radioligand binding assays with use of Sf9 cells, transiently expressing human H4R. Pharmacological studies results allowed to identify 4-[(E)-2-(3-chlorophenyl)ethenyl]-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine (Ki Combining double low line 253 nM) as the most potent compound in the present series.

Nickel-catalyzed highly regio- and stereoselective cyclization of oxanorbornenes with alkyl propiolates: A novel method for the synthesis of benzocoumarin derivatives

7-Oxabenzonorbornadienes bearing various substituents react with propiolates in the presence of [NiBr2(dppe)] (dppe = bis(diphenylphosphanyl)ethane) as a catalyst precursor and zinc powder to give benzocoumarin derivatives [Eq. (1)]. The one-pot reactions proceed at 80°C in acetonitrile, and the products are obtained in good yields with high regio- and stereoselectivity.

Fluoromorphic substrates for fatty acid metabolism: Highly sensitive probes for mammalian medium-chain acyl-CoA dehydrogenase

(Chemical Equation Presented) Not fussy: A systematic study revealed considerable substrate tolerance of medium-chain acyl-CoA dehydrogenase (MCAD), a member of the β-oxidation pathway for the degradation of fatty acids. Three fluorogenic reporter substra

Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

Palladium-Catalyzed Decarbonylative Heck Coupling of Aromatic Carboxylic Acids with Terminal Alkenes

A palladium-catalyzed decarbonylative alkenylation of aromatic carboxylic acids was developed. Under the reaction conditions, various benzoic acids including those bearing functional groups coupled to terminal alkenes, producing the corresponding internal alkenes in good to high yields. Cinnamic acids and bioactive benzoic acids such as 3-methylflavone-8-carboxylic acid, probenecid, adapalin, and febuxostat were also applicable to this reaction, demonstrating the potential synthetic value of this new reaction in organic synthesis.

Selenium-catalyzed C(sp3)-H acyloxylation: Application in the expedient synthesis of isobenzofuranones

Oxidative Se-catalyzed C(sp3)-H bond acyloxylation has been used to construct a diverse array of isobenzofuranones from simple ortho-allyl benzoic acid derivatives. The synthetic procedure employs mild reaction conditions and gives high chemoselectivity enabled by an inexpensive organodiselane catalyst. The presented approach offers a new synthetic pathway toward the core structures of phthalide natural products.

Phospholane-catalyzed wittig reaction

We identified 2-phenylisophosphindoline 2-oxide as a suitable and potentially tunable catalyst for the catalytic Wittig reaction of aldehydes with activated organohalides. This catalyst was obtained by a straightforward two-step synthesis. Trimethoxysilane proved to be an efficient reducing agent for the in situ generation and regeneration of the catalyst from the corresponding phosphane oxide. Sodium carbonate was identified as a suitable base for the transformation. It is noteworthy that the particle size of the sodium carbonate had a tremendous effect on the outcome of the reaction. Under the optimized reaction conditions, 23 aldehydes were converted into the corresponding alkenes in high isolated yields of up to 88%. Moreover, an asymmetric catalytic Wittig reaction was performed for the desymmetrization of a prochiral diketone.

Scope and Limitation of the Microwave-Assisted Catalytic Wittig Reaction

We have developed a microwave-assisted catalytic Wittig reaction. In this paper, we give full account of the scope and limitations of this reaction. A screening of various commercially available phosphine oxides as precatalysts revealed Bu3P=O to be the most promising candidate. We tested 10 silanes for the in situ reduction of the phosphine oxide to generate Bu3P as the actual catalyst. Different epoxides were tested as masked bases. In this context, cyclohexene oxide as well as butylene oxide proved to be suitable. The reaction could be carried out at 125 C, but higher yields and E/Z selectivities were obtained at 150 °C. Under the optimised reaction conditions, more than 40 examples for the conversion of various aldehydes into the corresponding alkenes are reported. The products were obtained in yields of up to 88 with high E selectivities. Moreover, we also describe the further screening of several chiral phosphines as catalysts for the microwave-assisted enantioselective catalytic Wittig reaction. The scope and limitations of the microwave-assisted catalytic Wittig reaction have been evaluated with respect to the catalyst, silane, solvent, reaction conditions, and substrates.

Synthesis and evaluation of (E)-2-(acrylamido)cyclohex-1-enecarboxylic acid derivatives as HCA1, HCA2, and HCA3 receptor agonists

2-(3-(Naphthalen-2-yl)propanamido)cyclohex-1-enecarboxylic acid and its 6-hydroxynaphthalen-2-yl analogue are well-known hydroxyl-carboxylic acid (HCA) receptor HCA2 agonists. A series of novel aryl derivatives of 2-amidocyclohex-1-ene carboxylic acid tha

First Microwave-Assisted Catalytic Wittig Reaction

We introduce a novel catalytic Wittig reaction based on an inexpensive and readily available phosphane oxide as a precatalyst. The performance of the reaction under microwave irradiation led to significantly improved yields and reaction rates relative to those obtained under conventional heating. Moreover, herein we enclose the first example of the asymmetric catalytic Wittig reaction based on a chiral phosphane as the catalyst.