Structure of 115595-27-2
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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. : | 115595-27-2 |
| Formula : | C11H12O3 |
| M.W : | 192.21 |
| SMILES Code : | O=C(O)C1=CC=C(OCCC=C)C=C1 |
| MDL No. : | MFCD00191325 |
| InChI Key : | QXZIOUAINSTHGI-UHFFFAOYSA-N |
| Pubchem ID : | 544452 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 |
* 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 |
|---|---|---|
| General procedure: Ethyl 4-(5-hexenyloxy)benzoate (1.2 g, 0.0048 mol) was added to a solution of sodium hydroxide (1.2 g, 0.030 mol) in 90 % methanol (30 mL). The solution was heated to reflux for 3 h. The solution was cooled and poured into 10 mL of 6 N HCl and the solution was then extracted with 30 mL of dichloromethane. The extraction solution was dried over anhydrous magnesium sulfate. Following removal of the solvent by evaporation under reduced pressure, the residue was purified by recrystallization from ethanol to yield 1.00 g (95 %) of white crystal. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dicyclohexyl-carbodiimide;dmap; In dichloromethane; at 20℃; | Example 10; Ethyl 8-(4-[4-(but-3-en-l-yloxy)bezoyloxy]phenyl)-2-(4-piperidinophenyl)-2-phenyl-2-H- naphtho[l,2-6]pyran-5-carboxylate (IUk) was prepared by the following procedure. Ethyl 8-(4-hydroxyphenyl)-2-(4-piperidinophenyl)-2-phenyl)-2-H-naphtho[l,2-6]pyran-5- carboxylate (obtained from ethyl 8-bromo-2-(4-piperidinophenyl)-2-phenyl)-2-H- naphtho[l,2-6]pyran-5-carboxylate and 4-hydroxyphenylboronic acid in the manner described for Example 1) 0.4g (0.69 mmol) and 4-(but-3-en-l-yloxy)benzoic acid 0.145 g (0.75 mmol) were dissolved in methylene chloride (30 ml). Dicyclohexyldiimide (DCC) 0.156g (0.75 mmol) and catalytic amount of dimethylaminopyridine (DMAP) were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered, the solvent was removed and the residue was flash chromatographed using petroleum ether - ethyl acetate (95-5) on silica gel. Recrystallization from ethyl acetate and hexane gave the title compound (m.p. 1000C; S=O.703). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 69% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 24h;Inert atmosphere; | General procedure: 4-(5-Hexenyloxy)benzoic acid (8) (1.6 g, 0.0081 mol) and 4-methoxyphenol (1 g, 0.0081 mol) dissolved in dry dichloromethane (100 mL), N,N-dicyclohexylcarbodiimide (DCC, 2.0 g, 0.0097 mol) and 4-(N,N-dimethylamino)pyridine (DMAP, 0.2 g) were added to react under nitrogen. The reaction mixture was stirred for 24 h at room temperature. The solution was filtered. After removal of the solvent by evaporation under reduced pressure, the residue was purified by recrystallization from ethanol to yield 1.74 g (66 %) of white crystal. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 86 g | With dmap; diisopropyl-carbodiimide; In dichloromethane; at 3 - 20℃; for 12h;Inert atmosphere; | Next, 60 g of the obtained compound (S-1-2), 73 g of the compound of (S-1-3)5.0 g of 4,4-dimethylaminopyridine was dissolved in 1,000 ml of dichloromethane and cooled to 3 C. under a nitrogen atmosphere.40 g of diisopropylcarbodiimide diluted with 200 ml of dichloromethane was added dropwise,After completion of the dropwise addition, the mixture was stirred at room temperature for 12 hours. After completion of stirring, the organic layer was washed with 10% hydrochloric acid,After washing with saturated brine, dichloromethane was distilled off under reduced pressure to obtain 140 g of crude product of (S-1-4).This was purified by column chromatography (silica gel, dichloromethane / ethyl acetate),And purified by recrystallization from methanol to give 86 g of the compound of (S-1-4). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 63 g | With water; sodium hydroxide; In ethanol; for 4h;Reflux; | 76 g of methyl 4-hydroxybenzoate, 54 g of 4-bromo-1-butene and 34 g of potassium carbonate were dissolved in 500 ml of dimethylformamide and stirred at 60 C. for 7 hours.The reaction solution was cooled to room temperature, 1000 ml of water and 100 ml of 10% hydrochloric acid aqueous solution were added,Extraction was performed using toluene, and toluene was distilled off under reduced pressure to obtain 93 g of a crude product of (S-1-1), 108 g.400 ml of water, 400 ml of ethanol and 20 g of sodium hydroxide were added thereto, followed by heating under reflux for 4 hours.After the reaction solution was cooled to room temperature, 500 ml of water was added, and a 10% hydrochloric acid aqueous solution was further added dropwise.The dropwise addition was continued until the aqueous layer became weakly acidic, and crystals precipitated. The precipitated liquid crystal was collected by filtration and dried to obtain 63 g of the compound of (S-1-2). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 71% | With [2,2]bipyridinyl; (1,2-dimethoxyethane)dichloronickel(II); water; bis(pinacol)diborane; lithium tert-butoxide; In methanol; N,N-dimethyl acetamide; at 30℃; for 24h;Schlenk technique; | Take a 10ml dry Schlenk reaction tube.In this order, for example, 0.3 mmol of B2Pin20.01 mmol NiCl 2 (DME),0.02 mmol organic ligand L4,0.2 mmol of the starting material (I) and 0.4 mmol of lithium t-butoxide were operated in a double-row tube three times;2 ml of DMA was injected in sequence, 50 ul of water, 0.1 mmol of methanol, and then vigorously stirred at 30 C for 24 h.After the reaction was completed, the pH was adjusted to 2 by adding 1 M hydrochloric acid, and then 20 ml of water was added thereto, and extracted with 20 ml of ethyl acetate, and the organic phase was collected and washed with saturated brine.It is dried over anhydrous magnesium sulfate, concentrated, and then separated with a 200 mesh silica gel column.Thus, the product (II) was obtained in a yield of 71%. |
| 71% | With 6,6'-dimethyl-2,2'-bipyridine; (1,2-dimethoxyethane)dichloronickel(II); bis(pinacol)diborane; lithium tert-butoxide; In methanol; N,N-dimethyl acetamide; water; at 30℃; for 24h;Inert atmosphere; Glovebox; Sealed tube; | General procedure: In glovebox, B2pin2 (76.17 mg, 0.3 mmol, 1.5 equiv), NiCl2(DME) (2.20 mg, 0.01 mmol, 0.05 equiv),6,6-dimethyl-2,2-dipyridyl (3.68 mg, 0.02 mmol, 0.10 equiv), LiOtBu (32 mg, 0.4 mmol, 2.0 equiv), and protected phenol (if solid) (0.2 mmol) were added to an oven-dried tube. The reaction tube wasequipped with a magnetic stir bar and sealed with Teflon-lined cap, refilled the system with argonand performed two more evacuation-backfill cycles, protected phenol was added by syringe underargon flow (if liquid). DMA (2.00 mL), H2O (50 μL), MeOH (25 μL) were added to the tubesequentially. The reaction mixture turned dark and was stirred at 30 C for 24 h. When the reactionwas finished, 10 mL aqueous HCl (0.1 M) was added to the mixture and extracted with CH2Cl2 (2 ×10 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The resulting residue was purifiedby silica gel flash chromatography to give the product. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | With potassium tert-butylate; In tetrahydrofuran; at 20℃; for 24h;Inert atmosphere; | General procedure: To a solution of phenol (10.00 mmol) and K2CO3 (30.00 mmol) in acetone (30.00 mL) was added4-bromo-but-1-ene (1.22 mL, 12.00 mmol). The mixture was refluxed for 12 h. It was then cooledto RT and the solvent was removed in vacuo. The residue was partitioned between CH2Cl2 andsaturated brine and the aqueous layer was extracted with CH2Cl2 (2 x 10 mL). The combinedorganic extracts were washed with brine (2 x 10 mL), dried and concentrated in vacuo. Theresulting residue was purified by silica gel flash chromatography and concentrated in vacuo toprovide the title compounds. |

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