107487-41-2

Upstream product

• 959-27-3 (Z)-1,4-diphenylbut-2-ene-1,4-dione 
• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 
• 96-09-3 styrene oxide 
• 98-86-2 acetophenone 
• 15295-43-9 1-benzoyl-2-phenylcyclopropane 
• 66090-52-6 3,6-diphenyl-3,4,5,6-tetrahydropyrazine 
• 1145-92-2 (1SR,2SR)-phenyl(2-phenylcyclopropyl)ketone 
• 100-42-5 styrene 
• 7654-06-0 3-phenyl-2H-azirine 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 591-51-5 phenyllithium 
• 86769-17-7 3-iodo-3-phenylpropyl phenyl ketone 
• 1197195-65-5 C₁₃H₂₀OTe 
• 98-88-4 benzoyl chloride 

Downstream Products

• 113446-20-1 1,4-diphenyl-4-methoxy-1-butanone 
• 495-71-6 phenacylacetophenone 
• 86769-18-8 1,4-diphenylpentane-1,4-diol 
• 53910-00-2 1,4-diphenyl-4-penten-1-ol 
• 5604-61-5 4-ethoxy-1,4-diphenylbutan-1-one 

Relevant academic research and scientific papers

Synthesis of Substituted Furan/Pyrrole-3-carboxamides through a Tandem Nucleopalladation and Isocyanate Insertion

Access to furanyl- and pyrrolyl-3-carboxamides from readily available 3-alkyne-1,2-diols and 1-amino-3-alkyn-2-ols using isocyanate as amido surrogate is demonstrated. The approach constitutes a successful unprecedented combination of heteropalladation an

Total syntheses of hyperaspidinols A and B enabled by a bioinspired diastereoselective cascade sequence

A bioinspired acid-triggered hemiacetalization/dehydration/[3 + 3]-type cycloaddition cascade process was disclosed, diastereoselectively furnishing furo[2,3-b]chromene skeleton under mild conditions. The viability of this approach was demonstrated by syntheses of a series of furo[2,3-b]chromene and pyrano[2,3-b]chromene derivatives. The successful total syntheses of two lignan-phloroglucinol hybrids, hyperaspidinols A and B, exemplified the synthetic utility of our biomimetic methodology.

Nonclassical Mechanism in the Cyclodehydration of Diols Catalyzed by a Bifunctional Iridium Complex

1,4- and 1,5-diols undergo cyclodehydration upon treatment with cationic N-heterocyclic carbene (NHC)–IrIII complexes to give tetrahydrofurans and tetrahydropyrans, respectively. The mechanism was investigated, and a metal-hydride-driven pathway was proposed for all substrates, except for very electron-rich ones. This contrasts with the well-established classical pathways that involve nucleophilic substitution.

Synthesis of Aromatic Retinoids and Curcuminoids and Evaluation of their Antiproliferative, Antiradical, and Anti-inflammatory Activities

Natural retinoids and curcuminoids are known for their broad spectrum of biological properties, such as antioxidant, anti-inflammatory, antitumor, and so forth. In this work, a convenient synthesis of aromatic retinoids and curcuminoids from vinyl or allyl ketones, and the corresponding alcohols, using olefin metathesis as a key reaction, was elaborated. The best yields and diastereoselectivities were obtained from allylic or homoallylic alcohols by employing the two-step cross-metathesis/oxidation procedure. The synthesized analogues were tested for their antiproliferative activity on human cancer cell lines of various origin (leukemia CEM, adenocarcinoma MCF7, cervical carcinoma HeLa) as well as for their antioxidant and anti-inflammatory activity in vitro. All examined derivatives exhibited strong anti-inflammatory activity in vitro without affecting cell viability. They also showed strong cytotoxicity against leukemia cell line CEM, except for 18 and 35. The antioxidant activity of the tested compounds was rather weak.

A metal-free transformation of alkynes to carbonyls directed by remote OH group

A remote OH group-directed metal-free transformation of alkynes to carbonyl compounds has been developed. Using only HOAc and EtOH solvent, this reaction elegantly converts alkynes into valuable ketones by remote hydroxyl group activation. Through comparison and isotope labeling experiments, it was confirmed that the process operates via a hydration reaction involving an acetic acid molecule, instead of a water molecule.

Cleavage of 3-aryl-5,6-dihydro-4H-1,2-oxazines using zinc and aqueous chelating ethers: Efficient methodology for N-O bond cleavage

A mild and efficient methodology for single pot ring opening of 3-aryl-4H-1,2-oxazines to γ-hydroxy ketones was developed using zinc and aqueous chelating ethers. The ether acts as ligand and co-solvent for the reaction. The ability of zinc ions to form stable complexes with chelating ethers activates the zinc towards reduction. Water is the proton source.

Copper-catalyzed oxaziridine-mediated oxidation of C-H bonds

The highly regio- and chemoselective oxidation of activated C-H bonds has been observed via copper-catalyzed reactions of oxaziridines. The oxidation proceeded with a variety of substrates, primarily comprising allylic and benzylic examples, as well as one example of an otherwise unactivated tertiary C-H bond. The mechanism of the reaction is proposed to involve single-electron transfer to the oxaziridines to generate a copper-bound radical anion, followed by hydrogen atom abstraction and collapse to products, with regeneration of the catalyst by a final single-electron transfer event. The involvement of allylic radical intermediates was supported by a radical-trapping experiment with TEMPO.

Functionalized organozincates and organocuprates derived from γ-hydroxytellurides in the preparation of 1,4-hydroxyketones

A C-O-dianionic zincate was generated by a Te/Li exchange reaction of an alkyltelluride, followed by Li/Zn transmetallation and reaction with methyllithium. The reaction between the enantiomerically pure (99% ee) (R)-dianionic zincate and benzoyl chloride

New cleavage of the azirine ring by single electron transfer: The synthesis of 2H-imidazoles, pyridazines and pyrrolines

Here we report the first example of the dimerisation of azirines to 2H-imidazoles or 3,5-disubstituted pyridazines from a reaction promoted by FeCl2. An azirine complex with a radical structure is proposed as an intermediate. Cyclopropyl ketones and pyrrolines are isolated when the reaction is carried out in the presence of styrenes.

Oxazaborolidine-catalysed reduction of alk-2-ene-1,4-diones. A convenient access to chiral 1,4-diols

An efficient method for the preparation of C2-symmetric, chiral alk-2- ene-1,4-diols (4) has been achieved, based on the borane-mediated reduction of symmetric alk-2-ene-1,4-diones (2) in the presence of oxazaborolidine (R)- 1. In general, the presence of the double bond in 2 has been beneficial (compared with the related saturated 1,4-diketones 3) not only as far as the stereoselectivity in the reduction step is concerned, but also because it allowed us to remove meso-4 by chomatography and/or to improve the stereochemical purity of several resulting mixtures of diols 4 by Sharpless' epoxidation. Enantioenricbed compounds 4 have been readily reduced to saturated diols with negligible loss of optical purity.