Structure of 2744-50-5
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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. : | 2744-50-5 |
| Formula : | C30H28O4 |
| M.W : | 452.54 |
| SMILES Code : | O=C(C(C1=CC=CC2=C31)=CC=C3C4=CC=CC5=C4C2=CC=C5C(OCC(C)C)=O)OCC(C)C |
| English Name : | Diisobutyl perylene-3,9-dicarboxylate |
| MDL No. : | MFCD00191681 |
| InChI Key : | YLNJGHNUXCVDIX-UHFFFAOYSA-N |
| Pubchem ID : | 75973 |
| Num. heavy atoms | 34 |
| Num. arom. heavy atoms | 20 |
| Fraction Csp3 | 0.27 |
| Num. rotatable bonds | 8 |
| Num. H-bond acceptors | 4.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 139.05 |
| TPSA ? Topological Polar Surface Area: Calculated from |
52.6 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
4.67 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
8.12 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
7.36 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.77 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
7.75 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
6.73 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-7.67 |
| Solubility | 0.00000971 mg/ml ; 0.0000000214 mol/l |
| Class? Solubility class: Log S scale |
Poorly soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-9.08 |
| Solubility | 0.000000375 mg/ml ; 0.0000000008 mol/l |
| Class? Solubility class: Log S scale |
Poorly soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-9.96 |
| Solubility | 0.0000000491 mg/ml ; 0.0000000001 mol/l |
| Class? Solubility class: Log S scale |
Poorly soluble |
| GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
| BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
| P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-3.3 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
| Ghose? Ghose filter: implemented from |
None |
| Veber? Veber (GSK) filter: implemented from |
0.0 |
| Egan? Egan (Pharmacia) filter: implemented from |
1.0 |
| Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
3.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<3.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.7 |
* 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 |
|---|---|---|
| /BRN= 3468164/; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 74% | With sodium azide In tetrahydrofuran for 60h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 93% | With potassium hydroxide In ethanol for 72h; Reflux; | |
| With potassium hydroxide In ethanol | Potassium 3,9-perylene dicarboxylate Potassium 3,9-perylene dicarboxylate 3,9-Perylenedicarboxylic acid diisobutyl ester (500 mg, 1.1 mmol, 1 eq) was suspended in 200 mL EtOH, and 1 M aq. KOH (7 mL, 3.3 mmol, 3 eq) was added. The reaction mixture was refluxed for 16 h. The precipitate was filtered off and washed with EtOH as well as DCM to provide the title compound as a yellow powder (369 mg, 0.9 mmol, 80%). 1H NMR (400 MHz, MeOD, 333K) δ 6.87-6.82 (m, 2H, PDA aromatic H), 6.76 (dd, J=9.7, 7.5 Hz 4H, PDA aromatic H), 6.17 (d, J=7.7 Hz 4H, PDA aromatic H), 5.99 (ddd, J=8.6, 7.6, 1.2 Hz 4H, PDA aromatic H). HRMS (ESI): calcd. mass for C22H11O4-: ([M-H]-) 339.0663. found: 339.0653. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride With potassium hydroxide at 198℃; for 36h; Stage #2: With potassium carbonate In chlorobenzene at 42 - 70℃; Stage #3: 2-methyl-propan-1-ol In chlorobenzene at 30℃; Reflux; | 1.1; 1.2 Preparation of diisobutyl 3,9-perylene carboxylate and diisobutyl 3,10-perylene carboxylate First 3,4,9,10 perylene tetracarboxylic dianhydride was dissolved in the KOH solution, followed by heating up to 198 deg.] C, at a pressure of 2MPa for 36h and then the reaction was kept cooled under pressure, until the pressure was decreased to atmospheric, the temperature drop to 85 °C after hot filtration, the filtrate was finally adjusted to pH 4 with hydrochloric acid, filtered, and the filter was washed with water, and drying, to obtain a mixture of 3,9-perylenedicarboxylic acid and 3,10-perylenedicarboxylic acid. 1) Esterification: First, the mixture of 3,9-perylenedicarboxylic acid and 3,10-perylenedicarboxylic acid obtained in step (a) is dissolved in an organic solvent, After the temperature was raised to 42 to 45 ° C, the acylating agent was added dropwise,After the addition of the acylating agent, Adjust the pH to 6 ~ 7, and add acid and esterification catalyst, Then heated to 65 ~ 70 ° C, Insulation reaction 2 ~ 2. 5h after the temperature to reflux,Reflux reaction 2 ~ 3h,Cooling to 30 ~ 35 ° C,Then add isobutanol and then heated to reflux,Reflux 3 ~ 4h after vacuum distillation,A solid residue was obtained. The important parameters for the acylation reaction are PH,temperature,Time and catalyst, The invention adopts the optimization design of the above process parameters, The conversion of the reactants is high, And to achieve the two isomers are generated simultaneously, The yield of the desired product is high and the purity is good. (2) impurity removal: the solid residue dissolved in organic solvents, heated to 120 ~ 130 ° C after the addition of activated carbon hot filter, the filtrate. Add activated charcoal to remove the coking impurities. (3) recrystallization: The filtrate was cooled to 35 ° C recrystallized diisobutyl 3,9-perylene carboxylate and diisobutyl 3,10-perylene carboxylate mixtures thereof. (4) Separation: Ethanol was added to the mixture of diisobutyl 3,9-perylene carboxylate and diisobutyl 3,10-perylene carboxylate obtained in step (3) and heated to reflux, filtered and the filtrate was reduced Pressure distillation, drying, That isdiisobutyl 3,9-perylene carboxylate After the filtrate is dried, diisobutyl 3,10-perylene carboxylate. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / 72 h / Reflux 2: potassium carbonate; tetrabutylammomium bromide; potassium iodide / water / 12 h / Reflux |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: potassium hydroxide / ethanol / 72 h / Reflux 2: potassium carbonate; tetrabutylammomium bromide; potassium iodide / water / 12 h / Reflux 3: pyridine; dmap / dichloromethane |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With butyltin(IV) chloride dihydroxide at 170℃; for 3h; | 1 Example 1 Take 0.1g (452g/mol, 0.22mmol)Diisobutyl 3,9-nonanedicarboxylate in a round bottom flask, adding 1.63g(298 g/mol, 5.5 mmol) of 2-octyldodecanol was heated to 100 ° C,Add 0.01 g (10 wt%) of dihydroxybutyl tin chloride to the reaction flask,The temperature was raised to 170 ° C, and the reaction was heated for 3 h, and the plate was tracked during the reaction.After the reaction, the reaction was cooled to room temperature and the temperature was raised to 180 ° C.Vacuum distillation,Distilling off excess 2-octyldodecanol which acts as both a solvent for the reaction and a reactantDry in vacuum. The resulting product was cooled to room temperature and dissolved in petroleum ether.The wet method was purified by silica gel column to obtain a yellow dye. The conversion was calculated to be 90%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With butyltin(IV) chloride dihydroxide at 175℃; for 3h; | 5 Example 5 0.1 g (452 g/mol, 0.22 mmol) of diisobutyl 3,9-nonanedicarboxylate was placed in a round bottom flask, and 1.63 g was added.(298 g/mol, 5.5 mmol) of 3-octyldodecanol was heated to 80 ° C, and 0.01 g (10 wt%) of dihydroxybutyltin chloride was added.In the reaction flask, the temperature was raised to 175 ° C, and the reaction was heated for 3 h, and the plate was tracked during the reaction. After the reaction, the reaction is coldBut to room temperature, the temperature is raised to 180 ° C, distilled under reduced pressure, and the excess is used as a reaction solvent and as a reactant.Octyldodecanol. The finally obtained product was cooled to room temperature, dissolved in petroleum ether, purified by wet silica gel column and dried in vacuo.Dry to give a yellow dye.The conversion was calculated to be 93.5%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 62% | With titanium(IV) isopropylate In toluene at 130 - 170℃; for 5h; | 3 Toluene (4 mL) was added to Solvent Green 5 (perylene diisobutyl isomer mixture) (1.06 g, 2.34 mmol), diethylene glycol monoisobutyl ether (0.93 g, 5.73 mmol), and titanium tetraisopropoxide (1.35 g, 4.75 mmol), and the mixture was heated to 130° C. and stirred for 2 hours while removing the distillate. The reaction solution was cooled to room temperature, and then cold water was added. The generated insoluble matter was removed by filtration, and the filtrate was extracted with ethyl acetate. Anhydrous sodium sulfate was added to the organic layer for dehydration, and the anhydrous sodium sulfate was removed by filtration. The filtrate was concentrated under reduced pressure to obtain 1.29 g of a mixture of 1-substituted form and 2-substituted form. Diethylene glycol monoisobutyl ether (1.86 g, 11.5 mmol), titanium tetraisopropoxide (0.67 g, 2.37 mmol) and anisole (6 mL) were further added, and the temperature was raised to 170° C. and the mixture was stirred for 3 hours while removing the distillate. After the reaction solution was cooled to room temperature, cold water was added, the generated insoluble matter was removed by filtration, and the filtrate was extracted with ethyl acetate. Anhydrous sodium sulfate was added to the organic layer for dehydration, and the anhydrous sodium sulfate was removed by filtration. The filtrate was concentrated under reduced pressure to obtain 1.48 g of a crude product. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate = 3/1), and a mixture containing compound A-4 represented by formula (A4-4) and isomers of compound A-4 (isomers of compound A-4 are presumed to be derived from the raw material) was obtained as a yellow-orange solid in a yield of 62% (0.92 g, 1.46 mmol) with a production ratio of (compound A-4): (isomers of compound A-4) = 0.9:1.1. |