Structure of 3478-88-4
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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. : | 3478-88-4 |
Formula : | C17H18O |
M.W : | 238.32 |
SMILES Code : | CC1=CC(C)=C(C=C1)C(=O)C1=C(C)C=C(C)C=C1 |
MDL No. : | MFCD00060094 |
InChI Key : | KFNQSAKXSGGDAA-UHFFFAOYSA-N |
Pubchem ID : | 12274022 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H317-H319 |
Precautionary Statements: | P280-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 |
---|---|---|
With hydrogenchloride; n-butyllithium; In tetrahydrofuran; | EXAMPLE 59 1,1-Bis(2,4-dimethylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanol. A solution of 1,5-dimethyltetrazol (8.9 g, 91.0 mmoles) in 100 mL of dry tetrahydrofuran at -60 C. was treated with n-butyl lithium (48 mL of 1.89M solution, 91.0 mmoles). After stirring for 20 minutes, <strong>[3478-88-4]2,2',4,4'-tetramethylbenzophenone</strong> (18 g, 76 mmoles) [prepared by the procedure described in J. Am. Chem. Soc., 81, 4858 (1959)] in 50 mL dry tetrahydrofuran was added and the solution was stirred for 1 hour during which time it was allowed to warm to -20 C. The reaction was quenched with 1N HCl, then extracted with chloroform. The combined organic extracts were dried (MgSO4) and evaporated to give 22 g of the title compound; m.p.=175-177 C. IR (KBr) νmax: 3390 (br), 1620 (s), 1460 (s), 1200 (s), 820 (s) cm-1; 1 H NMR (CDCl3) δ: 7.26 (2H, d), 6.95-6.83 (4H, m), 4.00 (1H, s), 3.82 (2H, s), 3.41 (3H, s), 2.23 (6H, s), 1.83 (6H, s) ppm; 13 C NMR (CDCl3) δ: 152.34, 139.28, 137.32, 135.79, 133.24, 126.26, 125.92, 77.47, 35.04, 32.99, 21.28, 20.76 ppm; Anal. Calcd. for C20 H24 N4 O: C, 71.41; H, 7.20; N, 16.67. Found: C, 70.82; H, 7.26; N, 16.45. | |
With hydrogenchloride; n-butyllithium; In tetrahydrofuran; | EXAMPLE 15 1,1-Bis(2,4-dimethylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanol A solution of 1,5-dimethyltetrazole (8.9 g, 91.0 mmoles) in 100 mL of dry tetrahydrofuran at -60 C. was treated with n-butyl lithium (48 mL of 1.89M solution, 91.0 mmoles). After stirring for 20 minutes, 2,2',4,4'tetramethylbenzophenone (18 g, 76 mmoles) [prepared by the procedure described in J. Am. Chem. Soc., 81, 4858 (1959)] in 50 mL dry tetrahydrofuran was added and the solution was stirred for 1 hour during which time it was allowed to warm to -20 C. The reaction was quenched with 1N HCl, then extracted with chloroform. The combined organic extracts were dried (MgSO4) and evaporated to give 22 g of the title compound; m.p.=175-177 C. IR (KBr) νmax: 3390 (br), 1620 (s), 1460 (s), 1200 (s), 820 (s) cm-1. 1 H NMR (CDCl3) δ: 7.26 (2H, d), 6.95-6.83 (4H, m), 4.00 (1H, s), 3.82 (2H, s), 3.41 (3H, s), 2.23 (6H, s), 1.83 (6H, s) ppm. 13 C NMR (CDCl3) δ: 152.34, 139.28, 137.32, 135.79, 133.24, 126.26, 125.92, 77.47, 35.04, 32.99, 21.28, 20.76 ppm. Anal. Calcd. for C20 H24 N4 O: C, 71.41; H, 7.20; N, 16.67. Found: C, 70.82; H, 7.26; N, 16.45. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; ammonia; sodium; | EXAMPLE 5 0.5 g of Fe(NO3)3.9H2 O and 49 g of sodium are added to liquid ammonia (1.5) to produce sodium amide. Then acetylene gas is introduced into the reaction mixture at a temperature of -40 C. to -65 C. (whilst cooling using dry ice-methanol) for one hour while stirring. Then, an anhydrous tetrahydrofuran solution containing 476 g of di-(2,4-dimethylphenyl) ketone is added dropwise to the reaction mixture while cooling and stirring. After further stirring for 2 hours, the mixture is left at room temperature overnight. After removal of ammonia from the reaction solution by evaporation, 3N diluted HCl (300 ml) is added to the solution. After extraction with ether, the ether layer is washed with water and dried. After removal of ether by evaporation, 1,1-bis(2,4-dimethylphenyl)-2-propyn-1-ol is obtained as colourless oily product with a yield of 450 g. |
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