159386-48-8

Upstream product

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 1079-66-9 chloro-diphenylphosphine 
• 645-59-0 dihydrocinnamonitrile 
• 4559-70-0 Diphenylphosphine oxide 
• 13338-63-1 2-(3,4,5-trimethoxyphenyl)acetonitrile 
• 159386-45-5 (α-Chloro-3,4,5-trimethoxybenzyl)diphenylphosphine oxide 

Downstream Products

• 61240-22-0 dehydrobrittonin A 
• 134029-62-2 (E)-3,4,4',5-tetramethoxystilbene 
• 134029-63-3 3,4,5,2'-tetramethoxy-trans-stilbene 
• 121042-96-4 (E)-1-(3',4',5'-Trimethoxyphenyl)-2-(4''-methoxy-3''-tert-butyldimethylsiloxyphenyl)ethene 
• 117048-59-6 trans-combretastatin A-4 

Relevant academic research and scientific papers

Preparation method of arylalkyl phosphorus oxide compounds

A preparation method of arylalkyl phosphorus oxide compounds is provided. The invention discloses a preparation method of several arylalkyl phosphorus oxide compounds. The preparation method includes:taking diphenylphosphine oxyhydrogen of 1.3 equivalent, 2.5% by mass nickel catalyst (with or without ligands) or palladium catalyst with ligands and a base of 1.5 equivalent from a glovebox, addingthem sequentially into a Schlenk reaction tube, adding a nitrile compound of 1.0 equivalent, vacuumizing, and backfilling with nitrogen; in the nitrogen atmosphere, adding a solvent, and allowing reaction to occur continuously at 120 DEG C for 16 h; after reaction, cooling to room temperature, and performing column chromatography separation to obtain the target product under high selectivity and high yield. The preparation method herein allows sp3C-CN\P-H cross coupling; reaction conditions are mild; operating is easy; the preparation process is simple; the target product has high conversion rate and high yield; the problems of other synthetic methods are solved that, for instance, two-step reaction system is complex, many organic and inorganic byproducts are produced, environmental pollution is caused easily, and the substrate range is narrow; the preparation method has a good industrial application prospect.

Catalytic sp3C-CN Bond Cleavage: Ni-Mediated Phosphorylation of Alkylnitriles

A direct phosphorylation of the sp3C-CN bond catalyzed by a nickel catalyst is disclosed. A wide range of primary nitriles readily coupled with secondary phosphine oxides to produce the corresponding phosphorylated products in high yields. As a key step, this new method was applied to the synthesis of anticancer drug Combretastatin-A4, significantly shortening its synthetic path.

The synthesis of (E) and (Z)-combretastatins A-4 and a phenanthrene from Combretum caffrum

The synthesis of the trans stilbene E-combretastatin A-4 has been achieved via a Horner-Wittig reaction of (3,4,5- trimethoxybenzyl)diphenylphosphine oxide. The anticancer drug Z- combretastatin A-4 was prepared by the hydroboration/protonation of a diaryl- alkyne.

Efficient synthesis of benzylphosphine oxides and E-stilbenes

A series of substituted benzylphosphine oxides has been synthesized by reduction of the corresponding (α-chlorobenzyl)phosphine oxide, derived from the benzaldehyde and chlorodiphenylphosphine, with either sodium borohydride (DMSO, 60-70 °C, 12 h) or tributyltin hydride and AIBN (C6H6, 80 °C, 2 h). Reaction of the (α-lithiobenzyl)phosphine oxide with aldehydes gave exclusively E-alkenes.