Structure of 82304-66-3
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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. : | 82304-66-3 |
Formula : | C17H24O3 |
M.W : | 276.37 |
SMILES Code : | O=C1OC2(C=C(C(C)(C)C)C(C(C(C)(C)C)=C2)=O)CC1 |
MDL No. : | MFCD00733511 |
InChI Key : | ZTMZUYHXZPUDRF-UHFFFAOYSA-N |
Pubchem ID : | 545303 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-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 |
---|---|---|
87% | Product 2b (0.1g, 0.47 mmol) was dissolved in chloroform (5 ml) and triphenylphosphine(0,13g, 0.49 mmol) added. The reaction mixture was stirred until starting peroxide wasconsumed as determined by TLC (between 10 - 20 mins). para-Toluene sulfonic acid (9 mg,0.05 mmol) was added and the reaction heated to 50C. After 4 h, the reaction mixture wasreduced to dryness and purified directly by column chromatography to give the titlecompound (0.074g, 87%); IR (neat)/cm-1:2957, 1774, 1647; 1H NMR (500 MHz, CDCl3): delta6.51 (s, 2H), 2.77 (t, J = 8.3 Hz, 2H), 2.28 (t, J = 8.3 Hz, 2H), 1.23 (s, 18H); 13C NMR (125MHz, CDCl3):185.5, 175.8, 147.7, 137.1, 79.9, 34.9, 33.3, 29.3, 28.6; HRMS (ESI) calculatedfor C17H24O3Na [M+Na]+: 299.161762; found: 299.161663. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With cesium hydroxide; oxygen; triethyl phosphite; In dimethyl sulfoxide; at 25℃; under 760.051 Torr; for 12h; | General procedure: CsOH (7.5 mg, 0.05 mmol), P(OEt)3 (167 mg, 1.0 mmol), 3(0.5 mmol) were added to a 25 mL Schlenk tube with a magnetic bar under O2. DMSO (2.0 mL) was added and then the mixture was stirred at room temperature (25 C) under O2 (1 atm) for 12 h. The solution was then diluted with ethyl acetate (10 mL), washed with brine (3 mL), extracted with ethyl acetate (3×5 mL), dried over anhydrous Na2SO4, filtered, and evaporated under vacuum. The crude reaction mixture was purified by column chromatographyon silica gel to get the desired product 4.. |