703-03-7

Usage

Organophosphorus compound

Contains a phosphorus atom and a five-membered ring with a phosphorus and carbon atom

Use as a ligand

Commonly used in coordination chemistry

Use as a building block

For the synthesis of various organic compounds

Potential applications in catalysis

Particularly in the field of asymmetric synthesis

Potential use in materials science

Such as in the development of organic light-emitting diodes and other electronic devices

Versatile and important compound

Wide range of potential applications

Upstream product

• 2501-98-6 diallyl(phenyl)phosphine oxide 
• 5186-73-2 1-phenyl-3-phospholene 1-oxide 
• 98-80-6 phenylboronic acid 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 

Downstream Products

• 131480-35-8 6,6-dimethyl-1-oxide-1-phenyloctahydro-1H-phospholo<2,3-d>pyrrolo<1,2-b>isoxazole 
• 139254-73-2 (3S*,3aS*,4R_P*,6aS*)-3-methoxycarbonyl-2-methyl-4-phenyl-3,3a,4,5,6,6a-hexahydro-2H-phospholo<2,3-d>isoxazole 4-oxide 
• 139402-34-9 (+)-(S)-2,3-dihydro-1-phenyl-1H-phosphole 1-oxide 
• 171598-28-0 (R)-(-)-2,3-dihydro-1-phenyl-1H-phosphole oxide 
• 154878-85-0 (1S,3aR,7S,8S,8aR,8bR)-(+)-7,8-di-tert-butoxy-1-phenyloctahydro-1H-pyrrolo<1,2-b>phospholo<2,3-d>isoxazole 1-oxide 
• 125344-77-6 4-Bromo-1-phenyl-2-phospholene 1-oxide 
• 142386-31-0 (+/-)-erythro 2-bromo-3-hydroxy-1-phenylphospholane 1-oxide 
• 142386-31-0 (+/-)-threo 2-bromo-3-hydroxy-1-phenylphospholane 1-oxide 
• 52988-62-2 1-phenyl-2-phospholen-1-sulfide 
• 139254-74-3 (3S*,3aS*,4R_P*,6aS*)-3,4-diphenyl-2-methyl-3,3a,4,5,6,6a-hexahydro-2H-phospholo<2,3-d>isoxazole 4-oxide 

Relevant academic research and scientific papers

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

A series of 1-substituted-3-methyl-2-phospholene oxides was prepared from the corresponding 3-phospholene oxides by double bond rearrangement. The 2-phospholene oxides could be obtained by heating the 3-phospholene oxides in methanesulfonic acid, or via the formation of cyclic chlorophosphonium salts. Whereas mixtures of the 2- and 3-phospholene oxides formed, when the isomerization of 3-phospholene oxides was attempted under thermal conditions, or in the presence of a base. The mechanisms of the various double bond migration pathways were elucidated by quantum chemical calculations.

Dynamic Kinetic Resolution in Rhodium-Catalyzed Asymmetric Arylation of Phospholene Oxides

The reaction of 2,5-dihydro-1H-phosphole 1-oxide 1 with ArB(pin) 3 in the presence of a chiral (R)-segphos-rhodium catalyst under highly basic conditions (10 equiv of KOH) gave high yields of (1S,3S)-3-arylphospholane 1-oxide 4 with high diastereoselectivity as well as high enantioselectivity. Equilibration of 1 with its 2,3-dihydro isomer 2, which is chiral and racemic, by base-catalyzed olefin isomerization followed by kinetic resolution of 2 with the chiral rhodium catalyst realized the present dynamic kinetic resolution.

Preparation and characterization of novel 4-bromo-3,4-dimethyl-1-phenyl-2- phospholene 1-oxide and the analogous phosphorus heterocycles or phospha sugars

4-Bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (3c) was first synthesized from 3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (2c) by a bromo-radical substitution reaction occurred at C-4 position by N-bromosuccinimide and 2,2′-azobisisobutyronitrile. The novel phospha sugar analogue 3c exerted high anti-proliferative effect on U937 cells evaluated by MTT in vitro methods and was much more efficient than that of Gleevec, which is known as a molecule targeting chemotherapeutical agent. The substitution of 2-phospholenes at C-3 and C-4 position with methyl groups as well as 4-bromo substituent suggests a good anti-proliferative effect.