52692-51-0

Upstream product

• 25542-62-5 6-bromo-hexanoic acid ethyl ester 
• 2996-92-1 phenyl trimethylsiloxane 
• 13159-24-5 ethyl 6-iodohexanoate 
• 122822-50-8 6-<(4-methylbenzenesulfonyl)oxy>hexanoic acid, ethyl ester 
• 100-58-3 phenylmagnesium bromide 
• 104-53-0 3-phenyl-propionaldehyde 
• 623-51-8 ethyl 2-sulfanylacetate 
• 19493-09-5 Methylenetriphenylphosphorane 
• 768-56-9 4-Phenylbut-1-ene 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 64-17-5 ethanol 
• 5581-75-9 6-phenylhexanic acid 
• 4119-41-9 1-iodo-3-phenylpropan 
• 140-88-5 ethyl acrylate 

Downstream Products

• 89108-84-9 4-Hydroxy-1-phenyl-3-(4-phenyl-butyl)-1H-[1,8]naphthyridin-2-one 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 21325-53-1 5-(4-phenyl-butyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 100316-77-6 6-phenyl-hexanoic acid hydrazide 

Relevant academic research and scientific papers

Visible-light induced metal-free cascade Wittig/hydroalkylation reactions

Cascade reactions are green and powerful transformations for building multiple carbon-carbon bonds in one step. Through a relay olefination and radical addition process, we were able to develop the cascade Wittig/hydroalkylation reactions induced by visible light. This metal-free radical approach features mild conditions, robustness, and excellent functionality compatibility. It allows access to saturated C3 homologation products directly from aldehydes or ketones. The synthetic utility of this method is demonstrated by a two-step synthesis ofindolizidine 209D.

Synthesis of Elongated Esters from Alkenes

A convenient method for synthesizing elongated aliphatic esters from alkenes is reported. An (alkoxycarbonyl)methyl radical species is generated upon visible-light irradiation of an ester-stabilized phosphorus ylide in the presence of a photoredox catalyst. This radical species adds onto the carbon–carbon double bond of an alkene to produce an elongated aliphatic ester.

Synthesis of 4-(ω-X-alkyl)benzonitriles (X = 1,3-dioxan-2-yl, CN, CO2Et) by the reaction of terephthalonitrile dianion with ω-X-alkyl bromides in liquid ammonia

The main products of the reaction of terephthalonitrile dianion disodium salt with ω-X-alkyl bromides (2-(2-bromoethyl)-1,3-dioxane, 5-bromovaleronitrile, ethyl 6-bromohexanoate) in liquid ammonia are the corresponding 4-(ω-X-alkyl)benzonitriles. Similar

Structure-Based Design of Potent Nicotinamide Phosphoribosyltransferase Inhibitors with Promising in Vitro and in Vivo Antitumor Activities

Inhibition of nicotinamide phosphoribosyltransferase (NAMPT) has the potential to directly limit NAD production in cancer cells and is an effective strategy for cancer treatment. Using a structure-based strategy, we have designed a new class of potent small-molecule inhibitors of NAMPT. Several designed compounds showed promising antiproliferative activities in vitro. (E)-N-(5-((4-(((2-(1H-Indol-3-yl)ethyl)(isopropyl)amino)methyl)phenyl)amino)pentyl)-3-(pyridin-3-yl)acrylamide, 30, bearing an indole moiety, has an IC50 of 25.3 nM for binding to the NAMPT protein and demonstrated promising inhibitory activities in the nanomolar range against several cancer cell lines (MCF-7 GI50 = 0.13 nM; MDA-MB-231 GI50 = 0.15 nM). Triple-negative breast cancer is the most malignant subtype of breast cancer with no effective targeted treatments currently available. Significant antitumor efficacy of compound 30 was achieved (TGI was 73.8%) in an orthotopic MDA-MB-231 triple-negative breast cancer xenograft tumor model. This paper reports promising lead molecules for the inhibition of NAMPT which could serve as a basis for further investigation.

Acceleration of CuI-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents using lithium chloride

In the presence of LiCl, CuI-catalyzed coupling reaction of R(alkyl)-X with Ar(aryl)MgBr at rt was completed within 2 h. Effective leaving groups X in R-X were Br, I, OTs, but not Cl. Grignard reagents ArMgBr with both standard and bulky Ar such as 2-MeC

Borohydride-mediated radical addition reactions of organic iodides to electron-deficient alkenes

Cyanoborohydrides are efficient reagents in the reductive addition reactions of alkyl iodides and electron-deficient olefins. In contrast to using tin reagents, the reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine or carbon-chlorine bond. The reaction system was successfully applied to three-component reactions, including radical carbonylation. The rate constant for the hydrogen abstraction of a primary alkyl radical from tetrabutylammonium cyanoborohydride was estimated to be 4 M-1 s-1 at 25 °C by a kinetic competition method. This value is 3 orders of magnitude smaller than that of tributyltin hydride.

Cross-coupling of alkyl halides with aryl or alkyl Grignards catalyzed by dinuclear Ni(ii) complexes containing functionalized tripodal amine-pyrazolyl ligands

Structurally distinctive dinuclear Ni(ii) complexes with furan or thiophene tethered amine-pyrazolyl tripodal hybrid ligands have been synthesized and crystallographically characterized. All complexes are catalytically active towards cross-coupling of aryl/alkyl Grignard reagents with β-H containing alkyl halides at room temperature in the presence of N,N,N',N'- tetramethylethylenediamine (TMEDA). The catalytic efficacy of the complexes is dependent on the tether substituent at the central amine. Two species, Ni(ii) TMEDA and Mg(ii) TMEDA complexes, have been isolated from the catalytic reaction mixtures under different conditions. Some ligand-stabilized Ni(ii) and Mg(ii) bimetallic species have also been identified in the ESI-MS spectra.

Iron-catalyzed cross-coupling of alkyl sulfonates with arylzinc reagents

Iron-catalyzed cross-coupling reactions of primary and secondary alkyl sulfonates with arylzinc reagents proceed smoothly In the presence of excess TMEDA and a concomitant magnesium salt. The arylzinc reagents are prepared from the corresponding aryllithium or magnesium reagents with ZnI2. The In situ formation of alkyl Iodides and consecutive rapid cross-coupling avoids discrete preparation of the unstable secondary alkyl halides and also achieves high product selectivity.

Iron-catalyzed chemoselective cross-coupling of primary and secondary alkyl halides with arylzinc reagents

Functional-group-compatible cross-coupling reaction of alkyl halides with arylzinc reagents takes place under iron catalysis in the presence of TMEDA, producing a variety of aromatic compounds in good to excellent yield. The pronounced effect of a magnesium salt was found to be the key to the promotion of the iron-catalyzed coupling reaction. Georg Thieme Verlag Stuttgart.

Room-temperature Hiyama cross-couplings of arylsilanes with alkyl bromides and iodides

The first method for achieving Hiyama couplings of unactivated alkyl bromides and iodides is reported. The desired carbon-carbon bond formation proceeds under mild conditions (room temperature) with good functional-group tolerance. Copyright