83816-47-1

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 18295-60-8 allenylmagnesium bromide 
• 53915-69-8 allenyltributylstannane 
• 18295-60-8 propargyl magnesium bromide 
• 865350-17-0 4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane 
• 106-96-7 propargyl bromide 
• 57186-58-0 2-allenyl-5,5-dimethyl-1,3,2-dioxaborinane 
• 146432-19-1 B-allenyl-9-BBN 

Downstream Products

• 215256-90-9 1-(4-nitrophenyl)buta-2,3-dien-1-one 
• 1356451-43-8 C₁₀H₈BrNO₃ 
• 10348-08-0 5-(4-nitrophenyl)-dihydro-2(3H)-furanone 

Relevant academic research and scientific papers

Catalytic propargylation of aldehydes with allenyltributylstannane by ytterbium triflate

The first ytterbium triflate [Yb(OTf)3]-catalyzed propargylation of various aldehydes with allenyltributylstannane to afford homopropargyl alcohols in good yields is described. The present result provides a versatile tool for preparation of an array of homopropargyl alcohols from the reaction of aldehydes with allenyltributylstannane; which are known to possess low reactivity.

Allenone-Mediated Racemization/Epimerization-Free Peptide Bond Formation and Its Application in Peptide Synthesis

Allenone has been identified as a highly effective peptide coupling reagent for the first time. The peptide bond was formed with an α-carbonyl vinyl ester as the key intermediate, the formation and subsequent aminolysis of which proceed spontaneously in a racemization-/epimerization-free manner. The allenone coupling reagent not only is effective for the synthesis of simple amides and dipeptides but is also amenable to peptide fragment condensation and solid-phase peptide synthesis (SPPS). The robustness of the allenone-mediated peptide bond formation was showcased incisively by the synthesis of carfilzomib, which involved a rare racemization-/epimerization-free N to C peptide elongation strategy. Furthermore, the successful synthesis of the model difficult peptide ACP (65-74) on a solid support suggested that this method was compatible with SPPS. This method combines the advantages of conventional active esters and coupling reagents, while overcoming the disadvantages of both strategies. Thus, this allenone-mediated peptide bond formation strategy represents a disruptive innovation in peptide synthesis.

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

The propargylation of aldehydes promoted by microwave irradiation using allenylboron compounds in a chemo- and regioselective way is described. The corresponding products were obtained in short reaction time, high yield and purity without the need of any solvent when allenylboronic acid pinacol ester was used, or using a minimal amount of acetone when potassium allenyltrifluoroborate was used.

ANTICANCER PRODRUG FOR OVERCOMING DRUG RESISTANCE

Disclosed is an anticancer prodrug that disturbs energy metabolism in cancer cells to overcome drug resistance. The anticancer prodrug has a structure including a pyruvate dehydrogenase kinase (PDK) inhibitor moiety, a mitochondrial targeting group, and a

A facile lipase-catalyzed KR approach toward enantiomerically enriched homopropargyl alcohols

Compounds possessing propargylic (prop-2-ynylic) system are very important building blocks for organic chemistry. Among them, preparation of enantiomeric homopropargyl alcohols (but-3-yn-1-ols) constitutes a key-challenge for asymmetric synthesis and thus

A bicyclization reaction with two molecular allenyl ketones and isocyanides: Synthesis of a lactone-containing azaspirocycle derivative

A novel bicyclization reaction of two molecular allenyl ketones and isocyanides has been disclosed. This strategy allows for the construction of structurally complex spirocyclic lactam-lactone systems in an efficient manner. This protocol also demonstrate

Overcoming Drug Resistance by Targeting Cancer Bioenergetics with an Activatable Prodrug

Nearly without exception, all known cancer chemotherapeutics elicit a resistance response over time. The resulting resistance is correlated with poor clinical outcomes. Here, we report an approach to overcoming resistance through reprogramming oncogene-di

Regioselective propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil

The propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil, an inexpensive and readily available clay, in a chemo- and regioselective way is described. The method is simple and avoids the use of air and moisture sensitive organometallics and products were obtained in good to moderate yields.

Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate

Zinc amide catalyzed, regioselective allenylation and propargylation of ketones with allenyl boronate is reported. Tertiary allenyl and homopropargyl alcohols were obtained, respectively, in high selectivities, from the same starting materials, simply by changing the reaction conditions. The substrate scope was wide. Mechanistic studies suggest that the reactions are controlled under kinetic and thermodynamic conditions.

Propargylation of aldehydes using potassium allenyltrifluoroborate

The commercially available resin Amberlyst A-31 was efficiently used to promote the propargylation of aldehydes using potassium allenyltrifluoroborate. The method is simple and fast, and the products were obtained in short reaction times in high yields and purity at room temperature in a regio- and chemoselective manner.