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Structure of 162709-84-4
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 162709-84-4 |
Formula : | C43H79ClO3 |
M.W : | 679.54 |
SMILES Code : | CCCCCCCCCCCCOC1=C(C(OCCCCCCCCCCCC)=CC(CCl)=C1)OCCCCCCCCCCCC |
MDL No. : | MFCD31697662 |
InChI Key : | TZPUTMAFBSQBFS-UHFFFAOYSA-N |
Pubchem ID : | 66959757 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H335-H314 |
Precautionary Statements: | P260-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P403+P233-P405-P501 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
91% | With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 5h; | A mixture of methyl 3,4,5-trihydroxybenzoate (1.03 g, 5.59 mmol), 7 (11.4 g, 16.8 mmol), and K2CO3 (6.95 g, 50.3 mmol) was stirred in DMF (80 mL) for 5 h at 70 C. After the reaction mixture was poured into water, the resulting precipitate was collected by filtration and subjected to column chromatography (SiO2, CHCl3) to afford the product ester (10.7 g, 91%) as a colorless solid. 1H NMR (270 MHz, CDCl3) δ 0.88 (t, J=6.6 Hz, 27H, CH3), 1.17-1.52 (m, 162H), 1.62-1.82 (m, 18H), 3.75 (t, J=6.6 Hz, 4H, -OCH2-), 3.88 (s, 3H, -OCH3), 3.88 (t, J=6.6 Hz, 10H, -OCH2-), 3.93 (t, J=6.6 Hz, 4H, -OCH2-), 5.03 (s, 4H, ArCH2OR), 5.04 (s, 2H, ArCH2OR), 6.60 (s, 2H, ArH), 6.63 (s, 4H), 7.38 (s, 2H, ArH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With pyridine; thionyl chloride; In tetrahydrofuran; at 20℃; for 1.5h; | A mixture of 23 (2.00 g, 3.03 mmol), THF (30 mL), pyridine (0.733 mL, 9.09 mmol) and thionyl chloride (0.456 mL, 6.06 mmol) was stirred at ambient temperature for 1.5 h. After filtration, solvent inthe filtrate was removed under reduced pressure to give 1.96 g (95 %) of 24 as brown oil |
95% | With thionyl chloride; In dichloromethane; at 20℃; for 3h; | Next, the compound shown in Chemical formula C is chlorinated with SOCl 2,To obtain the compound shown in Chemical Formula D.In this case, CH 2 Cl 2 was used as a solvent,The reaction was carried out at room temperature for 3 hours. The yield was 95%. |
92% | With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 0.5h; | A mixture of 3,4,5-tridodecyloxybenzyl alcohol (5.49 g, 8.30 mmol), thionyl chloride (0.844 mL, 11.6 mmol), and DMF (0.10 mL) was stirred in CH2Cl2 (55 mL) for 30 min at room temperature. Removal of the solvent and excess thionyl chloride under reduced pressure gave 7 (5.20 g, 92%) as a colorless solid. 1H NMR (270 MHz, CDCl3) δ 0.88 (t, J=6.6 Hz, 9H, CH3), 1.15-1.40 (m, 48H), 1.40-1.54 (m, 6H, -O(CH2)2CH2-), 1.73 (tt, J=7.2, 7.2 Hz, 2H, -OCH2CH2-), 1.79 (tt, J=7.2, 7.2 Hz, 4H, -OCH2CH2-), 3.94 (t, J=7.2 Hz, 2H, -OCH2-), 3.97 (t, J=7.2 Hz, 4H, -OCH2-), 4.51 (s, 2H, CH2Cl), 6.56 (s, 2H, ArH); 13C NMR (68 MHz, CDCl3) δ 14.1, 22.7, 26.08, 26.11, 29.35, 29.37, 29.39, 29.60, 29.63, 29.65, 29.69, 29.72, 29.74, 30.32, 31.92, 31.94, 47.0, 69.1, 73.4, 107.1, 132.3, 153.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | at 90℃; for 6h; | next,The compound shown in Chemical Formula D was reacted with N (CH 2 CH 3) 3 at 90 C. for 6 hours,To give the compound shown in Chemical Formula E. The yield was 68%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium azide; In N,N-dimethyl-formamide; at 70℃; for 1.5h; | To 24 (1.96 g, 2.88 mmol) in DMF (30 mL), sodium azide (0.468 g, 7.20 mmol) was added. The mixture was stirred at 70 C for 1.5 h and was poured into water (100 mL). It was extracted with diethylether, and the combined organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporation to give of 25 as pale yellow oil |