(DHQ)2PHAL
hydroquinine 1,4-phthalazinediyl diether
CAS: 140924-50-1
Molecular Formula: C48H54N6O4
(DHQ)2PHAL - Names and Identifiers
| Name | hydroquinine 1,4-phthalazinediyl diether |
| Synonyms | (DHQ)2PHAL (DHQ)2 PHAL (DHQ)2-PHAL 1,4-Bis(dihydroquinine)phthalazine 1,4-Bis(9-O-dihydroquininyl)phthalazine hydroquinine 1,4-phthalazinediyl diether 1,4-Bis((1R)-((1S,2S,4S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine (8alpha,9R,8'''alpha,9'''R)-9,9'-[phthalazine-1,4-diylbis(oxy)]bis(6'-methoxy-10,11-dihydrocinchonan) 4-((R)-((2S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-1-((R)-((2S,4R)-8-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine |
| CAS | 140924-50-1 |
| InChI | InChI=1/C48H54N6O4/c1-5-29-27-53-21-17-31(29)23-43(53)45(35-15-19-49-41-13-11-33(55-3)25-39(35)41)57-47-37-9-7-8-10-38(37)48(52-51-47)58-46(44-24-32-18-22-54(44)28-30(32)6-2)36-16-20-50-42-14-12-34(56-4)26-40(36)42/h7-16,19-20,25-26,29-32,43-46H,5-6,17-18,21-24,27-28H2,1-4H3/t29-,30-,31-,32-,43-,44-,45+,46+/m0/s1 |
| InChIKey | YUCBLVFHJWOYDN-PPIALRKJSA-N |
(DHQ)2PHAL - Physico-chemical Properties
| Molecular Formula | C48H54N6O4 |
| Molar Mass | 778.98 |
| Density | 1.30±0.1 g/cm3(Predicted) |
| Melting Point | 178°C (dec.)(lit.) |
| Specific Rotation(α) | 336 º (C=1.2 IN MEOH) |
| Solubility | Chloroform (Slightly), DMSO (Sligthly, Sonicated), Methanol (Slightly) |
| Appearance | White to light brown powder |
| Color | White to Off-White |
| BRN | 5475677 |
| pKa | 9.61±0.70(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 1.688 |
| MDL | MFCD00191975 |
(DHQ)2PHAL - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 9 |
(DHQ)2PHAL - Reference Information
| Application | Hydroquinine 1,4-(2, 3-diazaphthalene) diether Chinese alias Hydroquinine 1, 4-phthalazine diether is a chiral catalyst. Quinine is a very famous natural medicine. It has saved countless lives and is even considered to have affected the development process of human beings. The research on quinine has also left a very important record in the history of science. According to the chemical structure classification, quinine belongs to quinoline alkaloids (quinolines). From a biological point of view, this type of alkaloid is believed to be derived from o-aminobenzoic acid (o-aminobenzoic acid), and its parent structure contains the quinoline parent skeleton. Quinoline alkaloids are also the most numerous and complex alkaloids. The molecular composition, stereochemical structure, stereosynthesis and biological activity research of these alkaloids attract many organic chemists and pharmaceutical researchers. |
| Preparation | Preparation of hydrogenated quinine 1,4-(2, 3-diazaphthalene) diether from 1,4-dichlorophthalazine and hydrogenated quinine under alkaline conditions. The preparation reaction formula is as follows: hydroquinine 1,4-(2,3-diazaphthalene) diether preparation reaction formula Add 50 mL of sulfolane to a 250 mL flask, add 1,4-dichlorophthalazine and hydroquinine under stirring, then add potassium carbonate, stir and heat to 150 ℃ for reaction, and then control sampling analysis after 9 h of reaction, the content of hydroquinine is less than 0.5% (GC content) as the end point of the reaction. If it does not reach the end of the reaction, continue the heat preservation reaction until the end of the reaction. After the reaction is over, cool down to below 100 ℃, add 100 mL of hot water, raise the temperature to 95 ℃, and stir for 2 hours. After stirring, let it stand and layer, and the upper water layer is removed. The lower organic layer is washed twice with 200 mL of water, each time with 100 mL of water (the method of water washing is: heating to 95 ℃, stirring for 2 h, standing and layer, and the upper water layer is removed). Merge the upper water solution three times and wait for the next step to recover sulfolane. After washing, add 150 mL of water to the organic layer, raise the temperature to 95 ℃, stir for 2 hours, let stand and layer, and separate the upper water layer. Finally, 100 mL of water is added to the organic layer, heated to 95 ℃ and stirred for 30 min, then cooled down and crystallized. Cool down to about 35 ℃ and filter. After the filter cake is washed with water, it is dried to obtain hydrogenated quinine. |
| Use | Ligands are used for asymmetric dihydroxylation of unsaturated esters and trisubstituted C = C bonds. |
Last Update：2024-04-09 21:04:16
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