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Chemical Structure| 2744-50-5 Chemical Structure| 2744-50-5

Structure of 2744-50-5

Chemical Structure| 2744-50-5

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4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of [ 2744-50-5 ]

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

Safety of [ 2744-50-5 ]

Computational Chemistry of [ 2744-50-5 ] Show Less

Physicochemical Properties

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
Ertl P. et al. 2000 J. Med. Chem.

52.6 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

4.67
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

8.12
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

7.36
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

5.77
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

7.75
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

6.73

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-7.67
Solubility 0.00000971 mg/ml ; 0.0000000214 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-9.08
Solubility 0.000000375 mg/ml ; 0.0000000008 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-9.96
Solubility 0.0000000491 mg/ml ; 0.0000000001 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-3.3 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

1.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

1.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

3.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<3.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.7

Application In Synthesis of [ 2744-50-5 ]

* 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.

  • Downstream synthetic route of [ 2744-50-5 ]

[ 2744-50-5 ] Synthesis Path-Downstream   1~10

YieldReaction ConditionsOperation in experiment
/BRN= 3468164/;
  • 3
  • [ 2744-50-5 ]
  • [ 156-87-6 ]
  • [ 862288-27-5 ]
YieldReaction ConditionsOperation in experiment
74% With sodium azide In tetrahydrofuran for 60h; Heating;
  • 4
  • [ 2744-50-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation 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.
  • 5
  • [ 78-83-1 ]
  • [ 128-69-8 ]
  • [ 1059120-35-2 ]
  • [ 2744-50-5 ]
YieldReaction ConditionsOperation 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.
  • 6
  • [ 2744-50-5 ]
  • [ 2117096-24-7 ]
YieldReaction ConditionsOperation 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
  • 7
  • [ 2744-50-5 ]
  • [ 2117096-25-8 ]
YieldReaction ConditionsOperation 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
  • 8
  • [ 5333-42-6 ]
  • [ 2744-50-5 ]
  • [ 2307730-87-4 ]
YieldReaction ConditionsOperation 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%.
  • 9
  • [ 2744-50-5 ]
  • [ 2307730-88-5 ]
  • [ 2307730-89-6 ]
YieldReaction ConditionsOperation 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%.
  • 10
  • [ 18912-80-6 ]
  • [ 2744-50-5 ]
  • [ 3059849-63-4 ]
YieldReaction ConditionsOperation 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.
 

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