169233-83-4

Upstream product

• 3378-82-3 1-bromo-2-naphthaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 925441-39-0 2-ethenylnaphthalene-1-carbaldehyde 
• 2065-66-9 methyl-triphenylphosphonium iodide 

Downstream Products

• 1365840-95-4 benzyl[(2-ethenylnaphthalen-1-yl)methyl]amine 
• 1365840-96-5 tert-butyl N-benzyl-N-[(2-ethenylnaphthalen-1-yl)methyl]-carbamate 
• 1365840-97-6 tris(propan-2-yl)silyl N-benzyl-N-[(2-ethenylnaphthalen-1-yl)methyl]carbamate 
• 1365840-98-7 tris(propan-2-yl)silyl N-benzyl-N-[(2-formylnaphthalen-1-yl)methyl]carbamate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel (-)-cercosporamide derivatives as potent selective PPARγ modulators

Selective peroxisome proliferator-activated receptor gamma (PPARγ) modulators are expected to be a novel class of drugs improving plasma glucose levels without PPARγ-related adverse effects. As a continuation of our studies for (-)-Cercosporamide derivatives as selective PPARγ modulators, we synthesized substituted naphthalene type compounds and identified the most potent compound 15 (EC50 = 0.94 nM, Emax = 38%). Compound 15 selectively activated PPARγ transcription and did not activate PPARα and PPARδ. The potassium salt of compound 15 showed a high solubility and a good oral bioavailability (58%). Oral administration of the potassium salt remarkably improved the plasma glucose levels of female Zucker diabetic fatty rats at 1 mg/kg. Moreover, it did not cause a plasma volume increase or a cardiac enlargement in Wistar-Imamichi rats, even at 100 mg/kg.

A New Member of the BN-Phenanthrene Family: Understanding the Role of the B - N Bond Position

3,4-Dihydro-4-aza-3-boraphenanthrene, which shows the highest fluorescence quantum yield of all nonsubstituted BN-phenanthrenes reported to date (φF = 0.61), has been synthesized in only three steps (76% overall yield) from easily accessible 1-bromo-2-vinylnaphthalene, along with several substituted derivatives. The reactivity of these previously unknown BN-aromatic compounds toward organolithium compounds and bromine has been studied. This latter reaction affords bromo-substituted compounds that are suitable for further functionalization via Suzuki and Sonogashira couplings, with complete regioselectivity. The optical properties and excited state deactivation mechanisms of selected compounds were studied using computational methods.

Carbosulfenylation of Alkenes with Organozinc Reagents and Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate

The electrophilic alkylthiolation of alkenes, initiated by dimethyl(methylthio)sulfonium salts and the subsequent addition of various heteronucleophilies has been well-established. Regarding the use of carbon nucleophiles, however, only carefully designed sp-type carbon sources have been successfully applied. We herein present our findings on the methylthiolation of alkenes with dimethyl(methylthio)sulfonium trifluoromethanesulfonate, followed by carbon-carbon bond formation in the presence of organozinc reagents, thus achieving a catalyst-free protocol toward to the carbosulfenylation of alkenes.

Intramolecular Crossed [2+2] Photocycloaddition through Visible Light-Induced Energy Transfer

Herein, we present the intramolecular [2+2] cycloadditions of dienones promoted through sensitization, using a polypyridyl iridium(III) catalyst, to form bridged cyclobutanes. In contrast to previous examples of straight [2+2] cycloadditions, these efficient crossed additions were achieved under irradiation with visible light. The reactions delivered desired bridged benzobicycloheptanone products with excellent regioselectivity in high yields (up to 96%). This process is superior to previous syntheses of benzobicyclo[3.1.1]heptanones, which are readily converted to B-norbenzomorphan analogues of biological significance. Electrochemical, computational, and spectroscopic studies substantiated the mechanism of triplet energy transfer and explained the unusual regiocontrol.

Catalytic Intramolecular Ketone Alkylation with Olefins by Dual Activation

Two complementary methods for catalytic intramolecular ketone alkylation reactions with unactivated olefins, resulting in Conia-ene-type reactions, are reported. The transformations are enabled by dual activation of both the ketone and the olefin and are atom-economical as stoichiometric oxidants or reductants are not required. Assisted by Kool's aniline catalyst, the reaction conditions can be both pH- and redox-neutral. A broad range of functional groups are thus tolerated. Whereas the rhodium catalysts are effective for the formation of five-membered rings, a ruthenium-based system that affords the six-membered ring products was also developed.

Copper-catalyzed regioselective ortho C-H cyanation of vinylarenes

A copper-based catalytic technique for the regioselective ortho C-H cyanation of vinylarenes has been developed. This method provides an effective means for the selective functionalization of vinylarene derivatives. A copper-catalyzed cyanative dearomatiz

Formation of optically pure cyclic amines by intramolecular conjugate displacement

Intramolecular conjugate displacement (ICD) has been applied to the Morita-Baylis-Hillman adducts formed from (5S)-5-(l-menthyloxy)-2(5H)-furanone and aldehydes that carry a protected β- or γ-amino group. DIBAL-H reduction of the resulting ICD products releases optically pure six- or seven-membered cyclic amines having a stereogenic center α to nitrogen.

A visible-light-mediated oxidative C-N bond formation/aromatization cascade: Photocatalytic preparation of N-arylindoles

Just add light and air: Structurally diverse N-arylindoles can be prepared from readily prepared o-styryl anilines through visible-light photocatalysis. The reaction, which is conducted open to air, is mediated by [Ru(bpz) 3](PF6)2 (bpz=2,2'-bipyrazine) and involves both C-N bond formation and aromatization (see scheme). Using suitably substituted substrates, a 1,2-carbon shift can be also incorporated into this cascade reaction. Copyright

NOVEL CERCOSPORAMIDE DERIVATIVE

The present invention relates to a novel cercosporamide derivative, a pharmacologically acceptable salt thereof or an ester thereof which has an excellent hypoglycemic effect and is useful as a therapeutic and/or prophylactic agent for diabetes. A cercosporamide derivative having the general formula (I): [wherein X represents an oxygen atom or the like, R1 represents a hydrogen atom or a C1-C6 alkyl group, R2 represents a hydrogen atom, a C1-C6 alkyl group or a C1-C6 halogenated alkyl group, R3 represents a hydrogen atom or a C1-C6 alkyl group, R4 represents a C6-C10 aryl group which may be substituted with one to five group(s) independently selected from Substituent Group a, or the like, n represents 1, 2 or 3, and Substituent Group a represents a halogen atom, a C1-C6 alkyl group, a C1-C6 halogenated alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 alkoxy group, a C1-C6 halogenated alkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group and the like], a pharmacologically acceptable salt thereof or an ester thereof.

Synthesis of a new olefin polymerization catalyst supported by an sp 3-C donor via insertion of a ligand-appended alkene into the Hf-C bond of a neutral pyridylamidohafnium trimethyl complex

A new living and isoselective propylene polymerization precatalyst was generated via the intramolecular insertion of a ligand-appended vinyl group into the Hf-C bond of a neutral pyridylamidohafnium trimethyl complex. The Royal Society of Chemistry.