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Chemical Structure| 13081-18-0 Chemical Structure| 13081-18-0

Structure of 13081-18-0

Chemical Structure| 13081-18-0

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Product Details of [ 13081-18-0 ]

CAS No. :13081-18-0
Formula : C5H5F3O3
M.W : 170.09
SMILES Code : O=C(OCC)C(C(F)(F)F)=O
MDL No. :MFCD00114935
InChI Key :KJHQVUNUOIEYSV-UHFFFAOYSA-N
Pubchem ID :2737239

Safety of [ 13081-18-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H302-H315-H319
Precautionary Statements:P305+P351+P338
Class:3
UN#:3272
Packing Group:

Computational Chemistry of [ 13081-18-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 0.6
Num. rotatable bonds 4
Num. H-bond acceptors 6.0
Num. H-bond donors 0.0
Molar Refractivity 27.83
TPSA ?

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

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.39
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

1.48
Log Po/w (WLOGP)?

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

1.94
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.

0.46
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

1.27
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.31

Water Solubility

Log S (ESOL):?

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

-1.56
Solubility 4.65 mg/ml ; 0.0274 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-2.0
Solubility 1.71 mg/ml ; 0.0101 mol/l
Class?

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

Very 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

-1.19
Solubility 11.0 mg/ml ; 0.0644 mol/l
Class?

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

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
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

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.

-6.29 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

0.0
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)

1.56

Application In Synthesis of [ 13081-18-0 ]

* 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 [ 13081-18-0 ]

[ 13081-18-0 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 2934-05-6 ]
  • [ 13081-18-0 ]
  • (S)-3-hydroxy-5,7-diisopropyl-3-(trifluoromethyl)benzofuran-2(3H)-one [ No CAS ]
  • 2
  • [ 455-37-8 ]
  • [ 13081-18-0 ]
  • C12H9F4NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 98 A^-[10,ll-dichloro-4-oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02'6]dodeca- l(12),6,8,10-tetraen-3-yl]-<strong>[455-37-8]3-fluorobenzamide</strong> (ABR 239440) To a stirred solution of <strong>[455-37-8]3-fluorobenzamide</strong> (500 mg, 3.59 mmol) in DMF (5 mL) was added pyridine (306 mu, 3.59 mmol) followed by ethyl 3,3,3-trifluoro-2-oxopropanoate (476 mu, 3.59 mmol) at room temperature under argon. The reaction mixture was stirred at room temperature for 1 h. Thionyl chloride (231 mu, 3.18 mmol) was added at 0C and the reaction mixture was then stirred at room temperature for 2.5 h. The reaction mixture was concentrated. The acyl intermediate that remained was dissolved in DMF (2 mL) under argon. 5,6-Dichloro-lH-l ,3- benzodiazol-2 -amine (545 mg, 2.70 mmol) and triethylamine (503 mu, 3.59 mmol) were added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried ( a2S04), filtered and concentrated. The crude product was purified by silica chromatography, using 3% MeOH in DCM as eluent. Further purification was carried out by trituration in DCM/MeOH and then pentane to afford the title compound as an off-white solid (22 mg, 1%).
  • 3
  • [ 13081-18-0 ]
  • 3,4-dimethoxybenzenediazonium tetrafluoroborate [ No CAS ]
  • [ 300374-83-8 ]
  • 4
  • [ 5654-97-7 ]
  • [ 13081-18-0 ]
  • (Z)-ethyl 3,3,3-trifluoro-2-(2-oxo-1H-pyrrolo[2,3-b]pyridin-3(2H)-ylidene)propanoate [ No CAS ]
  • 5
  • [ 526-47-6 ]
  • [ 13081-18-0 ]
  • C15H15F4NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With diphenyl hydrogen phosphate; (2S)-2-[[[[3,5-bis(trifluoromethyl)phenyl]amino]oxomethyl]amino]-N-(diphenylmethyl)-N,3,3-trimethylbutyramide; In hexane; at 20℃; for 41.5h;Molecular sieve; Organic urea catalyst (2S) -2-[[[[[3,5-bis (trifluoromethyl) phenyl] amino] oxomethyl] amino] -N- (diphenylmethyl) -N, 3,3-trimethylbutyramide (45mg, 0.08mmol), <strong>[526-47-6]2,3-dimethyl-5-fluoroindole</strong> (65.1mg, 0.4mmol), diphenyl phosphate (10.2mg, 0.04mmol) and molecular sieve (201.5 mg) was dissolved in n-hexane (16 mL), and then ethyl trifluoropyruvate (106 muL, 0.8 mmol) was added. The reaction was performed at room temperature for 41.5 hours. The reaction equation is as follows:The reaction solution was filtered with silica gel, rinsed with ether, and concentrated. 126 mg of liquid product was obtained by silica gel column chromatography. The calculated yield was 96%. The measured er value was 92: 8. Crystallize and concentrate the mother liquor to obtain 93 mg of liquid product. The calculated yield is 71%. The er value is 99: 1.
  • 6
  • [ 526-47-6 ]
  • [ 13081-18-0 ]
  • ethyl 3,3,3-trifluoro-2-((5-fluoro-3-methyl-1H-indol-2-yl)methyl)-2-hydroxypropanoate [ No CAS ]
  • ethyl (R)-3,3,3-trifluoro-2-((5-fluoro-3-methyl-1H-indol-2-yl)methyl)-2-hydroxypropanoate [ No CAS ]
 

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