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Structure of 260355-20-2

Chemical Structure| 260355-20-2

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Product Details of [ 260355-20-2 ]

CAS No. :260355-20-2
Formula : C7H3ClF3I
M.W : 306.45
SMILES Code : FC(F)(F)C1=C(Cl)C=CC(I)=C1
MDL No. :MFCD09037801
InChI Key :MCIFWVOVVPVBRJ-UHFFFAOYSA-N
Pubchem ID :43145392

Safety of [ 260355-20-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 260355-20-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 49.17
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.4
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

4.08
Log Po/w (WLOGP)?

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

5.12
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.

4.8
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

4.46
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.17

Water Solubility

Log S (ESOL):?

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

-4.61
Solubility 0.00745 mg/ml ; 0.0000243 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-3.79
Solubility 0.0503 mg/ml ; 0.000164 mol/l
Class?

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

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

-4.84
Solubility 0.00447 mg/ml ; 0.0000146 mol/l
Class?

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

Moderately 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

No
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

Yes
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

Yes
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.

-5.27 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

0.0
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

1.0 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<1.0
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)

1.83

Application In Synthesis of [ 260355-20-2 ]

* 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 [ 260355-20-2 ]

[ 260355-20-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 260355-20-2 ]
  • [ 108511-97-3 ]
  • N-(4-chloro-3-trifluoromethylphenyl)-isoxazole-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; In toluene; at 50℃; for 4h; The 1-chloro-4-iodo-2-trifluoromethylbenzene (10 mmol) obtained in the reaction 1.2 was dissolved in 20 ml of toluene, and the system was sequentially added with <strong>[108511-97-3]<strong>[108511-97-3]isoxazol-4-amin</strong>e</strong> (12 mmol), palladium acetate ( 0.5 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (12 mmol), 3 ml of triethylamine. After stirring for 10 minutes, add 10 ml of cesium carbonate (10 mmol). The aqueous solution was heated to 50 ° C for 4 hours. After the reaction was completed, 20 ml of water was added to the system, and the mixture was stirred for 20 minutes. The organic phase was dried over anhydrous sodium sulfate, concentrated, and then evaporated -(4-Chloro-3-trifluoromethylphenyl)-<strong>[108511-97-3]isoxazole-4-amine</strong> powder, yield 84percent.
84% 1-Chloro-4-iodo-2-trifluoromethylbenzene (10 mmol) obtained in Reaction 1.2 was dissolved in 20 ml of toluene, and <strong>[108511-97-3]isoxazole-4-amine</strong> (12 mmol) was sequentially added to the system, palladium acetate ( 0·5 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (12 mmol), 3 ml of triethylamine. After stirring for 10 minutes, add 10 ml of cesium carbonate (10 mmol). The aqueous solution is heated to 50 ° C for 4 hours. After the reaction is completed, 20 ml of water is added to the system, stirred for 20 minutes, and the organic phase is dried over anhydrous sodium sulfate, concentrated, and then purified by flash column chromatography to give 2.2 g. Yellow N-(4-chloro-3-trifluoromethylphenyl)-<strong>[108511-97-3]isoxazole-4-amine</strong> powder, yield 84percent
84% The 1-chloro-4-iodo-2-trifluoromethylbenzene (10 mmol) obtained in the reaction 1.2 was dissolved in 20 ml of toluene, and the system was sequentially added with <strong>[108511-97-3]<strong>[108511-97-3]isoxazol-4-amin</strong>e</strong> (12 mmol), palladium acetate ( 0.5 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (12 mmol), 3 ml of triethylamine, stirred for 10 minutes,Add 10 ml of cesium carbonate (10 mmol) aqueous solution, and heat to 50 ° C for 4 hours. After the reaction is completed, add 20 ml of water to the system, stir for 20 minutes, separate the liquid, and dry the organic phase with anhydrous sodium sulfate. Column chromatography gave 2.2 g of yellow N-(4-chloro-3-trifluoromethylphenyl)-<strong>[108511-97-3]isoxazole-4-amine</strong> powder in a yield of 84percent
84% Dissolving 1-chloro-4-iodo-2-trifluoromethylbenzene (10 mmol) obtained in Reaction 1.220 ml of toluene,Isoxazole-4-amine is added sequentially to the system(12mmol),Palladium acetate (0.5 mmol),2,2'-bis(diphenylphosphino)-1,1'-binaphthyl(12 mmol), 3 ml of triethylamine, after stirring for 10 minutes, add 10 ml of cesium carbonate (10 mmol)The aqueous solution is heated to 50 ° C for 4 hours. After the reaction is completed, 20 ml of water is added to the system.Stir for 20 minutes, dispense,The organic phase is dried over anhydrous sodium sulfate. Concentrated, flash column chromatography,2.2 g of yellow N-(4-chloro-3-trifluoromethylphenyl)-<strong>[108511-97-3]isoxazole-4-amine</strong> powder was obtained with a yield of 84percent.
84% The 1-chloro-4-iodo-2-trifluoromethylbenzene (10 mmol) obtained in the reaction 1.2 was dissolved in 20 ml of toluene, and the system was sequentially added with <strong>[108511-97-3]<strong>[108511-97-3]isoxazol-4-amin</strong>e</strong> (12 mmol), palladium acetate ( 0.5 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (12 mmol), 3 ml of triethylamine. After stirring for 10 minutes, add 10 ml of cesium carbonate (10 mmol). The aqueous solution is heated to 50 ° C for 4 hours. After the reaction is completed, 20 ml of water is added to the system, stirred for 20 minutes, and the organic phase is dried over anhydrous sodium sulfate, concentrated, and then purified by flash column chromatography.2.2 g of yellow N-(4-chloro-3-trifluoromethylphenyl)-<strong>[108511-97-3]isoxazole-4-amine</strong> powder was obtained in a yield of 84percent.
84% With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; In toluene; at 50℃; for 4h; 1-Chloro-4-iodo-2-trifluoromethylbenzene (10 mmol) obtained in Reaction 1.2 was dissolved in 20 ml of toluene.Isoxazole-4-amine (12 mmol) was added sequentially to the system.Palladium acetate (0.5 mmol),2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (12 mmol),3 ml of triethylamine,After stirring for 10 minutes,Add 10 ml of aqueous solution of cesium carbonate (10 mmol),Heat to 50 ° C for 4 hours.After the reaction was completed, 20 ml of water was added to the system, and the mixture was stirred for 20 minutes, and the organic phase was dried over anhydrous sodium sulfate, concentrated, and purified by flash column chromatography.2.2 g of yellow N-(4-chloro-3-trifluoromethylphenyl)-<strong>[108511-97-3]isoxazole-4-amine</strong> powder was obtained in a yield of 84percent.
84% The 1-chloro-4-iodo-2-trifluoromethylbenzene (10 mmol) obtained in the reaction 1.2 was dissolved in 20 ml of toluene, and the system was sequentially added with <strong>[108511-97-3]<strong>[108511-97-3]isoxazol-4-amin</strong>e</strong> (12 mmol), palladium acetate ( 0.5 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (12 mmol), 3 ml of triethylamine. After stirring for 10 minutes, add 10 ml of cesium carbonate (10 mmol). The aqueous solution was heated to 50 ° C for 4 hours. After the reaction was completed, 20 ml of water was added to the system, stirred for 20 minutes, and the organic phase was dried over anhydrous sodium sulfate.Concentration and flash column chromatography gave 2.2 g of yellow N-(4-chloro-3-trifluoromethylphenyl)-<strong>[108511-97-3]isoxazole-4-amine</strong> powder, yield 84percent.

 

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