R-4-oxide-4-hydroxy-2,6-bis(4-nitrophenyl)- Dinaphtho[2,1-d
(11bR)-4-Hydroxy-2,6-bis(4-nitrophenyl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
CAS: 695162-89-1
Molecular Formula: C32H19N2O8P
R-4-oxide-4-hydroxy-2,6-bis(4-nitrophenyl)- Dinaphtho[2,1-d - Names and Identifiers
| Name | (11bR)-4-Hydroxy-2,6-bis(4-nitrophenyl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin |
| Synonyms | R-4-oxide-4-hydroxy-2,6-bis(4-nitrophenyl)- Dinaphtho[2,1-d R-3,3'-Bis(4-nitrophenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate (R)-3,3'-Bis(4-nitrophenyl)-1,1'-binapthyl-2,2'-diyl hydrogenphosphate |
| CAS | 695162-89-1 |
R-4-oxide-4-hydroxy-2,6-bis(4-nitrophenyl)- Dinaphtho[2,1-d - Physico-chemical Properties
| Molecular Formula | C32H19N2O8P |
| Molar Mass | 590.48 |
| Density | 1.59±0.1 g/cm3(Predicted) |
| Melting Point | 223.5-249.0 °C (decomp) |
| Boling Point | 856.0±75.0 °C(Predicted) |
| pKa | 1.08±0.20(Predicted) |
| Storage Condition | 2-8℃ |
R-4-oxide-4-hydroxy-2,6-bis(4-nitrophenyl)- Dinaphtho[2,1-d - Reference Information
| Application | (R)-3,3 '-bis (4-nitrophenyl)-1,1'-binaphthol phosphate is a chiral binaphthol-phosphoric acid derivative, which can be used as a catalyst for asymmetric Mannich-type reactions, asymmetric hydrophosphorylation reaction and asymmetric synthesis reaction of asymmetric N-heterodil Alder reaction. |
| preparation | 1) Add (R)-3 in a three-necked eggplant flask, 3 '-bis (dihydroxyborane)-2,2'-dimethoxy-1, 1 '-binaphthalene (4mmol), barium hydroxide 8 hydrate (12mmol), Pd(PPh3)4(0.28mmol) 1, 4-dioxane (24ml) and water (8ml) were stirred. 1-bromo-4-nitrobenzene (10mmol) was added dropwise to the solution and refluxed for 25 hours. Subsequently, 1, 4-dioxane was distilled off under reduced pressure, dichloromethane was added, washing was performed with 1M hydrochloric acid and a saturated aqueous solution of sodium chloride, and dehydration was performed with anhydrous sodium sulfate. Add the above product and 100ml of dichloromethane to a three-necked eggplant flask, cool to 0 °c, and add BBr3 Dropwise (18mmol,1 molar solution in dichloromethane). After completion of the dropwise addition, the mixture was stirred at room temperature for 8.5 hours, and then cooled to 0 ° C. Again, ml of water was added to stop the reaction. Washing was performed with water and a saturated aqueous solution of sodium chloride, followed by dehydration with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (Hexane: ethyl acetate = 5:1) to give (R)-3,3 '-bis (4-nitrophenyl)-1,1'-binaphthol (yield 82%). 2) Add (R)-3,3 '-bis (4-nitrophenyl)-1,1'-binaphthol (1mmol) and pyridine 1.4ml in a two-necked eggplant flask, POCl3(1.4mmol) was added dropwise over 3 minutes, and the mixture was stirred at room temperature for 2 hours. Water (150 μL) was added to the reaction solution, and the mixture was further stirred for 30 minutes. The pyridine was then distilled off from the reaction solution under reduced pressure. Subsequently, 6M hydrochloric acid (7ml) was added and refluxed for 2 hours. This was cooled, purified by silica gel column chromatography containing triethylamine, and a free product was formed using 6M hydrochloric acid. After dissolving it in a small amount of dichloromethane, it was precipitated by adding n-hexane to give (R)-3,3 '-bis (4-nitrophenyl)-1,1'-binaphthol phosphate (yield 62%). |
Last Update：2024-04-10 22:29:15
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Multiple Specifications
Product Name: (11bR)-4-Hydroxy-2,6-bis(4-nitrophenyl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin Visit Supplier Webpage Request for quotationCAS: 695162-89-1
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