Structure of 17919-34-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 17919-34-5 |
Formula : | C22H32O6P2 |
M.W : | 454.43 |
SMILES Code : | CCOP(=O)(CC1=CC=C(C=C1)C1=CC=C(CP(=O)(OCC)OCC)C=C1)OCC |
MDL No. : | MFCD01321144 |
InChI Key : | DRCOGQJUVZRNSQ-UHFFFAOYSA-N |
Pubchem ID : | 635132 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | at 150℃; for 12h;Inert atmosphere; | A mixture of 4,4?-bis(bromoethyl)biphenyl (1) (0.204 g, 0.592 mmol) and P(OEt)3 (1 mL, 6.27mmol) was heated at 150C for 12 h under N2. The mixture was purified over silica gel columnchromatography using ethyl acetate as eluant, giving 258 mg of 3.Yield : 96 %. 1H NMR (CDCl3, 400 MHz)delta 7.53 (d, J = 8.3 Hz, 4H), 7.36 (d, J = 8.3 Hz, 4H), 4.04(q, J = 7.1 Hz, 8H), 3.19 (d, J = 21.7 Hz, 4H), 1.27 (t, J = 7.1 Hz, 12H). |
96% | at 150℃; for 12h; | 4,4?-bis(bromoethyl)-1,1?-biphenyl (0.204 g, 0.592 mmol) and P(OEt)3 (1 ml, 6.27 mmol) were stirred at 150 for 12 hours. The mixture was then cooled to room temperature and the product was purified by column chromatography on silica gel (ethyl acetate). The product was isolated as a colorless solid (0.258 g, 96). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | at 159℃; for 4h; | 5.8 g (199.71 mmol) 4,4'-Bis-chloromethyldiphenyle were reacted with 105 g (600.00 mmol) triethylphosphite at 159C for 4 hours. The excess amount of triethylphosphite was distilled off. The residue was diluted with toluene. The precipitated product was filtered, washed with toluene and dried under reduce pressure. 53.2 g (59%) of a white solid was obtained. Melting point: 111 C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With potassium tert-butylate; In DMF (N,N-dimethyl-formamide); at 5 - 20℃; for 24h;Product distribution / selectivity; | 1.13 g of tetraethyl 4,4'-dimethylbiphenyl-alpha,alpha'-diyl-diphosphonate and 1.42 g of 2'-formyl-alpha-phenylstilbene were dissolved in 10 ml of N,N-dimethylformamide. At 5 to 10 C., 0.65 g of potassium tert-butoxide was gradually added to the reaction over 10 minutes. The reaction mixture was then stirred at room temperature for 24 hours. 30 ml of ethanol was then added. The precipitate was recovered by filtration, washed with water and then dried to obtain pale yellow powders. The pale yellow powders were then re-crystallized from toluene, to obtain 0.82 g of pale yellow needle crystals (yield 79%). The melting point thereof was 242.0 to 247.0 C. The elementary analysis of this product resulted in 93.89% carbon (theoretical value as compound 1-82: 94.08%), and 5.81% hydrogen (theoretical value as compound 1-82: 5.92%). In infrared absorption spectrum (KBr tablet), stretching vibration due to aromatic rings was recognized at around 1590 cm-1. In proton nuclear magnetic resonance spectrum (solvent CDCl3, internal standard TMS), ring protons of aromatic rings and alkene protons were recognized at delta=6.9 to 7.8 ppm (42H). In mass spectrum, a molecular ion peak m/z=714 was recognized. From these results, it was confirmed that the compound thus obtained was compound No.1-82 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With potassium tert-butylate; In DMF (N,N-dimethyl-formamide); at 5 - 20℃; for 20h;Product distribution / selectivity; | 4.54 g of tetraethyl 4,4'-dimethylbiphenyl-alpha,alpha'-diyl-diphosphonate and 2.64 g of 2-methylbenzaldehyde were dissolved in 40 ml of N,N-dimethylformamide. At 5 to 10 C., 2.60 g of potassium tert-butoxide was gradually added to the reaction over 10 minutes. Subsequently, the reaction mixture was stirred at room temperature for 20 hours, and then poured into a mixture consisting of 150 ml of water and 150 ml of ethanol. The precipitate was recovered by filtration, washed with water and then dried to obtain pale yellow crystals. The crystals were re-crystallized from a mixed solvent of toluene and ethanol, to obtain 1.88 g of pale yellow crystals (yield 49%). The elementary analysis of this product resulted in 93.09% carbon (theoretical value as compound2-17: 93.22%), and 6.60% hydrogen (theoretical value as compound 2-17: 6.78%). In infrared absorption spectrum (KBr tablet), stretching vibration due to aromatic rings was recognized at around 1600 cm-1. In mass spectrum, a molecular ion peak m/z=386 was recognized. From these results, it was confirmed that the compound thus obtained was compound No.2-17. |