75992-52-8

Upstream product

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 141-05-9 Diethyl maleate 
• 4192-77-2 ethyl cinnamate 
• 623-91-6 diethyl Fumarate 
• 64-17-5 ethanol 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 102-92-1 Cinnamoyl chloride 
• 75949-27-8 3-<7-(Cinnamoyloxy)heptyl>-6-<6-(cinnamoyloxy)hexyl>-2-pyridone 
• 75949-33-6 2-Methoxy-3-<7-(cinnamoyloxy)heptyl>-6-<6-(cinnamoyloxy)hexyl>pyridine 

Relevant academic research and scientific papers

Heteroleptic copper(I) complexes as energy transfer photocatalysts for the intermolecular [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides

The [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides can be effectively catalyzed by heteroleptic copper(I) complexes. The reactions were carried out under mild reaction conditions and the products were obtained in 20–72% yield under visible light irradiation. The copper-based photocatalyst comprised of the rigid phenanthroline ligand with substituents at the 2,9-positions and the 4,7-positions showed high activity in the photodimerization via an energy transfer pathway.

Donor-acceptor fluorophores as efficient energy transfer photocatalysts for [2 + 2] photodimerization

Mild [2 + 2] photodimerization of enone substrates was induced by donor-acceptor fluorophores. Enone substrates were activated efficiently for anti-head to head dimerizations with a high yield (up to 83%) and high selectivity. The adjustable excited state potential also allows donor-acceptor fluorophores to be used for isomerization of the above substrates, confirming the potential of donor-acceptor fluorophores as energy transfer photocatalysts.

Effect of Reaction Media on Photosensitized [2+2]-Cycloaddition of Cinnamates

The outcome of photosensitized [2+2]-cycloaddition reactions of various cinnamates has been compared in different reaction media, including homogeneous organic solutions under inert conditions, degassed water, and aerated physical gels. The reactions were performed under LED blue light (λmax=455 nm) irradiation and [Ir{dF(CF3)ppy}2(dtb-bpy)]PF6 (1.0 mol%) as photocatalyst. The processes were optimized taking into consideration solvent, gelator, and substrate. Comparative kinetics analyses, as well as the effect of the reaction media on the diastereoselectivity of the process, were evaluated during this investigation. In a number of cases, carrying out the reaction in a less polar solvent, like toluene or highly polar solvent, like water had a tremendous impact on the diastereoselectivity of the process, pointing towards an effect on the stabilization of the putative diradical intermediate in this medium. Moreover, while for reactions run in homogeneous solution oxygen needs to be excluded, no erosion in yield is observed when the photoadditions were run in aerated gel media.

General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible-Light Catalysis

[2+2] Photocycloaddition, for example, the dimerization of chalcones and cinnamic acid derivatives, is a unique strategy to construct cyclobutanes, which are building blocks for a variety of biologically active molecules and natural products. However, most attempts at the above [2+2] addition have focused on solid-state, molten-state, or host–guest systems under ultraviolet-light irradiation in order to overcome the competition of facile geometric isomerization of nonrigid olefins. We report a general and simple method to realize the intermolecular [2+2] dimerization reaction of these acyclic olefins to construct cyclobutanes in a highly regio- and diastereoselective manner in solution under visible light, which provides an efficient solution to a long-standing problem.

Photosensitised regioselective [2+2]-cycloaddition of cinnamates and related alkenes

An efficient method for the synthesis of substituted cyclobutanes from cinnamates, chalcones, and styrenes has been developed utilizing a visible-light triplet sensitisation mode. This reaction provides a diverse range of substituted cyclobutanes in high yields under mild conditions without the need of external additives. Good regioselectivity is obtained due to strong π-π-stacking of arene moieties, whereas diastereoselectivity relies on the electronic effects or ortho-substitution of the arene substrate. The utility of this transformation is demonstrated by the formal synthesis of the lignane natural product (±)-Tanegool.

Using non-covalent interactions to direct regioselective 2+2 photocycloaddition within a macrocyclic cavitand

The relative orientation of guests within ternary inclusion complexes is governed by the host-guest and guest-guest supramolecular interactions. Selectivity in 2+2 photocycloaddition between two alkenes included within a macrocyclic cavitand (γ-cyclodextrin) can be controlled using non-covalent interactions. In this manuscript, we report cavitand-mediated control of regioselectivity between alkyl cinnamates using non-covalent interactions. Using this method, we have shown that regioselectivity can be switched completely from a head-to-head dimer to a head-to-tail dimer. The reactions were also stereoselective in most cases. Stoichiometry experiments were performed to explore relative stabilities of the complexes, which indicate that the ternary complex is more stable than others. Selectivity in the photocycloaddition reaction was also applied retrospectively to deduce intermolecular orientations. Time-dependent conversion study we performed indicates that the observed reactivity of alkenes is representative of the intermolecular orientations in the bulk of the complex medium. Experimental observations and computational studies were used to qualitatively understand the complex structures, and relative magnitudes of the weak interactions. The reactions of complexes were studied in slurry form, and the extent of reaction control suggests a solid-state-like behavior.

Regio- and stereochemical control in the photodimerization of methyl 3-(2-furyl)acrylate

The photochemical dimerization of methyl 3-(2-furyl)acrylate in acetonitrile in the presence of benzophenone as triplet sensitizer was reinvestigated in order to understand regio- and stereochemical control. Hplc purification of the dimers and 1/sup

Photocycloaddition in Liquid Ethyl Cinnamate and in Ethyl Cinnamate Glasses. The Photoreaction as a Probe into the Micromorphology of the Solid

Irradiation of neat liquid ethyl cinnamate at room temperature and of ethyl cinnamate glasses at -80 and -196 deg C produces cyclodimers in high yield.Six of the possible eleven isomers have been identified in the products.Their contributions to the overa

Molecular Organization by Hydrogen Bonding: Juxtaposition of Remote Double Bonds for Photocyclization in a 2-Pyridone Dimer

Irradiation of the hydrogen bonded dimer of 3--6--2-pyridone (1) provides the δ-truxinic acid ester 3 and the β-truxinic acid ester 4, respectively.The photocyclization occurs via a 25-membered ring in yields