65473-85-0

Upstream product

• 70388-65-7 (Z)-1,4-diphenyl-1-butene 
• 637-59-2 1-Bromo-3-phenylpropane 
• 122-97-4 3-Phenyl-1-propanol 
• 100-39-0 benzyl bromide 
• 14213-84-4 2-phenylethylstyrene 
• 7484-37-9 (3-phenylpropyl)triphenylphosphonium bromide 
• 847946-85-4 4-(4-phenyl-cis-but-3-enyl)-pyridine 

Relevant academic research and scientific papers

Method used for direct synthesis of epoxy compounds from alcohol

The invention discloses a method used for direct synthesis of an epoxy compounds from an alcohol. According to the method, an alcohol is taken as a raw material, Swern oxidation is adopted to synthesize an aldehyde, a bromo-hydrocarbon and an alkali are added into the aldehyde directly to construct epoxy functional groups, and generate the epoxy compound. According to the method, one-pot method is adopted to realize direct epoxidation of the alcohol, the synthesis route is simple, the preparation process is easy to control, no catalyst is needed in the process, substrate suitable range is wide, reagents are cheap and easily available, preparation conditions are mild, reaction yield is high, and the method is suitable for synthesis of epoxy compounds.

Novel chiral (salen)Mn(iii) complexes containing a calix[4]arene unit in 1,3-alternate conformation as catalysts for enantioselective epoxidation reactions of (Z)-aryl alkenes

Two new chiral calix[4]arene-salen ligands 1a,b, based on calix[4]arene platforms in 1,3-alternate conformation, have been prepared by a new general synthetic pathway. Their Mn(iii) complexes, 3a,b, have shown fairly good efficiency in the asymmetric epoxidation of styrene and substituted styrenes, whereas excellent catalytic activity and selectivity were observed with rigid bicyclic alkenes, namely 1,2-dihydro-naphthalene and substituted 2,2′-dimethyl-chromene. The higher catalytic properties of 3a may be ascribed to the more rigid and inherently chiral structure as proved by molecular modelling, NMR spectroscopy and X-ray data of the similarly structured UO2 complexes 2a,b.

Conformationally restricted dynamic supramolecular catalysts for substrate-selective epoxidations

A second generation of a substrate-selective dynamic supramolecular catalytic system consisting of a catalyst part and a receptor part, connected by a hydrogen-bonding motif, has been realized based on rational design. The results from analyses of the equilibrium mixture of the species generated by the components of the first generation system led us to selectively lock the cisoid conformation of the catalyst part to increase the amount of the substrate-selective catalytic cavity in the equilibrium mixture. This was realized by strapping the catalyst part by organic synthesis. This strapping led to an increase in substrate selectivity in the pair-wise competitive epoxidations of pyridyl- vs. phenyl-appended styrenes and pyridyl- vs. phenyl-appended stilbenes of both Z- and E- configuration compared to the first generation system, reaching 3.4:1 as the highest substrate selectivity for Z-mono-pyridyl-stilbene (27a) vs. the corresponding all-carbon analogue (28a) and for E-dipyridyl-stilbene (26b) vs. the corresponding all-carbon analogue (28b), respectively.

Modulation of the reactivity, stability and substrate- and enantioselectivity of an epoxidation catalyst by noncovalent dynamic attachment of a receptor functionality - Aspects on the mechanism of the Jacobsen-Katsuki epoxidation applied to a supramolecular system

The synthesis of the components of the dynamic supramolecular hydrogen-bonded catalytic system 2 + 3 is described. The catalytic performance and substrate- and enantioselectivity of Mn(salen) catalyst 2 were investigated in the presence and absence of the Zn(porphyrin) receptor unit 3. The effects of pyridine and pyridine N-oxide donor ligands were also studied. Some aspects on the mechanism of the Jacobsen-Katsuki epoxidation, based on literature observations, are introduced as a means to analyse the behaviour of 2 and its modulation by the formation of macrocycle 1 with 3. A complete association model of the metal-free system 4 + 5 refutes the earlier assumption that macrocycle 1 is the predominant form of catalyst 2 under the standard epoxidation reaction conditions with 2 + 3. Evidence are provided that receptor-binding substrates and nonbinding substrates, respectively, are epoxidised by two different catalytic species, or two distinct distributions of species in competitive epoxidations using catalytic system 2 + 3. The two species are assigned to the endo and exo faces of the Mn(salen) catalyst in macrocycle 1, and to equivalently folded oligomeric structures with monomers 2 and 3 in adjacent positions. The Royal Society of Chemistry 2006.

Novel chiral (salen)MnIII complexes containing a calix[4]arene unit as catalysts for enantioselective epoxidation reactions of (Z)-aryl alkenes

New asymmetric (salen)MnIII and UO2 complexes containing a calix[4]arene unit in the ligand framework were synthesized. The UO2 complexes were characterized by 1H-, 13C-, 2D TOCSY and T-ROESY NMR spectroscopy. Furthermore, the structure of one UO 2 complex was determined by single-crystal X-ray analysis. The data showed that UO2 complexes, which can be considered in first approximation models of the Mn=O oxidant active species, possess a chiral pocket and adopt relevant conformations for the selectivity of the oxygen transfer process. Epoxidation data of model alkenes with the MnIII complexes showed moderate ee values and were not conclusive in indicating that the calix[4]arene unit might be able to influence the selectivity by a molecular recognition mechanism. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

A dynamic supramolecular system exhibiting substrate selectivity in the catalytic epoxidation of olefins

A dynamic supramolecular system involving hydrogen bonding between a Mn(III) salen catalyst and a Zn(II) porphyrin receptor exhibits selectivity for pyridine appended cis-β-substituted styrene derivatives over phenyl appended derivatives in a catalytic ep

Diastereoselective Friedel-Crafts cyclization reactions to 2-substituted 1-phenyl-1,2,3,4-tetrahydronaphthalenes

1′-Substituted 1-phenyl-1-(3′-phenylprop-1′-yl)alkenes, 1-substituted 2-methyl-4-phenylbutanols, and 2,5-diphenyl-3-methyl-2-pentanol were synthesized from known starting materials. These compounds and the known epoxide 2-phenethyl-3-phenyloxirane were su