92254-66-5

Upstream product

• 536-74-3 phenylacetylene 
• 2579-22-8 Phenylpropargyl aldehyde 
• 108-59-8 malonic acid dimethyl ester 
• 186581-53-3 diazomethane 
• 16900-64-4 4-phenylbut-1-en-3-yne-1,1-dicarboxylic acid 

Downstream Products

• 66684-74-0 dimethyl (E)-cinnamylidenemalonate 
• 1402578-94-2 C₁₉H₁₈O₅ 
• 1206604-33-2 dimethyl 2-(2-phenylethynyl)cyclopropane-1,1-dicarboxylate 

Relevant academic research and scientific papers

Three-Component Reaction of Dimethyl Malonate with α,β-Acetylenic Aldehydes and Amines. Synthesis of Push–Pull Buta-1,3-dienes

Abstract: Three-component reaction of dimethyl malonate with α,β-acetylenic aldehydes and cyclic secondary amines (pyrrolidine, piperidine, morpholine, and piperazine) under mild conditions afforded dimethyl 2-(3-aminoprop-2-en-1-ylidene)malonates in 50–9

Regioselective Synthesis of 5-Metalated 2-Pyrones by Intramolecular Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide

The oxyindation of carbonyl-ene-yne compounds with indium trihalides proceeded efficiently to give di-, tri-, and tetrasubstituted 2-pyrones bearing a carbon-indium bond. The metalated 2-pyrone and a zwitterion intermediate were identified by X-ray crystallographic analysis. The application of organoindium compounds to oxidation or cross-coupling provided easy access to various multifunctionalized 2-pyrones. Some 2-pyrone derivatives show intense fluorescence only in the solid state (aggregation-induced emission).

Phosphine-Mediated Dimerization of Conjugated Ene-Yne Ketones: Stereoselective Construction of Dihydrobenzofurans

A new strategy for the phosphine-mediated dimerization of conjugated ene-yne ketones to produce functionalized dihydrobenzofurans has been developed, affording diversified 4,5-dihydrobenzofurans in moderate to excellent yields with high diastereoselectivities under mild conditions. This new synthetic method can tolerate a variety of functional groups and can be performed on a gram scale and in an asymmetric variant using the chiral phosphine Xyl-BINAP to give the desired products with up to 94% ee. (Figure presented.).

Tetrahydro-1,3-oxazepines via Intramolecular Amination of Cyclopropylmethyl Cation

An efficient synthesis of tetrahydro-1,3-oxazepines was developed involving the regioselective intramolecular amination of cyclopropylmethyl cation. The cation was generated by the abstraction of one imidate group in bis-imidate bearing a carbocation-stabilizing substituent. Using 1,1,2,3-tetrasubstituted cyclopropane substrates, highly diastereoselective intramolecular amination to trans-tetrahydro-1,3-oxazepines was achieved. The resulting tetrahydro-1,3-oxazepines were transformed to the homoallylamine derivatives in high yields.

Organocatalytic asymmetric anti-selective Michael reactions of aldehydes and the sequential reduction/lactonization/pauson-khand reaction for the enantioselective synthesis of highly functionalized hydropentalenes

A new method has been developed for the enantioselective synthesis of highly functionalized hydropentalenes bearing up to four stereogenic centers with high stereoselectivity (up to 99% ee). This process combines an enantioselective organocatalytic anti-selective Michael addition with a highly efficient one-pot reduction/lactonization/Pauson-Khand reaction sequence. The structures and absolute configurations of the products were confirmed by X-ray analysis.