99254-92-9

Upstream product

• 766-82-5 1-ethynyl-3-methyl-benzene 
• 7681-65-4 copper(l) iodide 

Downstream Products

• 1310329-81-7 3-methylphenylethynyl diphenylphosphine oxide 

Relevant academic research and scientific papers

Design, Synthesis, and Bioactivities of Phthalide and Coumarin Derivatives Based on the Biosynthesis and Structure Simplification of Gossypol

Because gossypol and hemigossypol show antiviral activity but are structurally complex, we designed and synthesized a series of structurally simpler phthalide and coumarin derivatives. The phthalide derivatives were synthesized by opening the naphthalene ring of hemigossypol, and the coumarin derivatives were synthesized by ring-opening reactions of the phthalide derivatives with the goal of investigating the effect of the lactone ring size on bioactivity. The bioassay results showed that the two series of target compounds possessed moderate to good activities against tobacco mosaic virus, One of the compounds showed in vivo inactivation, curative, and protection activities of 50 ± 1, 53 ± 3, and 48 ± 2% at 500 mg/L, values which are higher than those of gossypol (32 ± 1, 35 ± 1, 29 ± 1%, respectively) and comparable to those of hemigossypol (55 ± 1, 49 ± 1, and 48 ± 1%, respectively) and the commercial antiviral agent ningnanmycin (56 ± 2, 54 ± 1, 58 ± 1%) at the same dose. Thus, this compound is a promising candidate for the development of new anti-plant-virus agents. In addition, most of the synthesized compounds showed broad-spectrum activity when tested against 14 kinds of phytopathogenic fungi and showed selectivity against Sclerotinia sclerotiorum, Physalospora piricola, and Rhizoctonia cerealis. Moreover, some of the compounds exhibited activity against Plutella xylostella larvae; the two most active compounds exhibited larvicidal activities (LC50) of 4.10 and 5.47 mg/L, respectively. Further studies showed that these compounds also exhibited insecticidal activities against Mythimna separata, Helicoverpa armigera, and Pyrausta nubilalis larvae.

Room-Temperature Alkynylation of Phosphine Oxides with Copper Acetylides: Practical Synthesis of Alkynylphosphine Oxides

An efficient procedure for the synthesis of alkynylphosphine oxides based on the oxidative alkynylation of secondary phosphine oxides with copper acetylides was developed. Activation with molecular oxygen in the presence of either a mixture of 1,2-dimethylimidazole and triethylamine or N-methylimidazole alone enabled the formal umpolung of the poorly nucleophilic copper acetylides, which were coupled with phosphine oxides under remarkably mild conditions. Notable features of this procedure are the availability of the starting materials, its user-friendliness, and its mild conditions, which allow the synthesis of complex alkynylphosphine oxides.

Tandem synthesis of 3-halo-5-substituted isoxazoles from 1-copper(I) alkynes and dihaloformaldoximes

A tandem synthesis of 3-halo-5-substituted isoxazoles has been developed from 1-copper(I) alkynes and dihaloformaldoximes under base-free conditions. Thus, 1,3-dipolar cycloaddition and all its drawbacks can now be avoided completely.

Room-temperature direct alkynylation of arenes with copper acetylides

C-H bond in azoles and polyhalogenated arenes can be smoothly activated by copper acetylides to give the corresponding alkynylated (hetero)arenes by simple reaction at room temperature in the presence of phenanthroline and lithium tert-butoxide under an oxygen atmosphere. These stable, unreactive, and readily available polymers act as especially efficient and practical reagents for the introduction of an alkyne group to a wide number of arenes under remarkably mild conditions.

Access to difluoromethylated alkynes through the castro-stephens reaction

An efficient synthesis of difluoromethylated alkynes is described. A panel of readily available CuI acetylides undergo direct difluoromethylation by using BrCF2CO2Et, which is an inexpensive, easy to handle, commercially available fluorinated reagent. The reaction, which is based on a Castro-Stephens transformation, proceeds smoothly under mild conditions offering a new synthetic route for the direct introduction of the difluoromethylated group into alkynes that does not involve ozone-depleting reagents. The resulting products were obtained with good yields by using CsOPiv and Cu(OAc)2 as additives.