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Structure of 2712-78-9

Chemical Structure| 2712-78-9

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Product Details of [ 2712-78-9 ]

CAS No. :2712-78-9
Formula : C10H5F6IO4
M.W : 430.04
SMILES Code : O=C(OI(C1=CC=CC=C1)OC(C(F)(F)F)=O)C(F)(F)F
MDL No. :MFCD00009672
InChI Key :PEZNEXFPRSOYPL-UHFFFAOYSA-N
Pubchem ID :102317

Safety of [ 2712-78-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Computational Chemistry of [ 2712-78-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 21
Num. arom. heavy atoms 6
Fraction Csp3 0.2
Num. rotatable bonds 7
Num. H-bond acceptors 10.0
Num. H-bond donors 0.0
Molar Refractivity 63.45
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.

0.0
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

5.01
Log Po/w (WLOGP)?

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

5.92
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.

2.91
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

3.51
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.47

Water Solubility

Log S (ESOL):?

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

-5.41
Solubility 0.00167 mg/ml ; 0.00000387 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.

-5.85
Solubility 0.000601 mg/ml ; 0.0000014 mol/l
Class?

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

Moderately 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

-4.4
Solubility 0.0171 mg/ml ; 0.0000398 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

High
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

Yes
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.

-5.37 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

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

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<2.0
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)

3.44

Application In Synthesis of [ 2712-78-9 ]

* 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 [ 2712-78-9 ]

[ 2712-78-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 110944-98-4 ]
  • [ 2712-78-9 ]
  • [ 64611-67-2 ]
  • Trifluoro-acetic acid 2-(4-nitro-phenyl)-2-oxo-ethyl ester [ No CAS ]
  • 2
  • [ 850144-81-9 ]
  • [ 2712-78-9 ]
  • [ 75-65-0 ]
  • [ 214973-83-8 ]
YieldReaction ConditionsOperation in experiment
60% (Referential Example 4) Synthesis of 1-bromo-4-(1-tert-butoxycarbonylamino-1-methylethyl)benzene (referential compound 4-1) In an argon stream, 260 g (600 mmol) of [bis(trifluoroacetoxy)iodo]benzene was added, at room temperature with stirring, to a solution of 99 g (410 mmol) of 4-(1-aminocarbonyl-1-methylethyl)-1-bromobenzene (referential compound 2-1) in 1,000 ml of tert-butanol and the mixture was stirred for 30 minutes under a condition of heating to reflux. After that, 100 ml (1,200 mmol) of pyridine was added thereto and the mixture was stirred for 1 hour under the condition of heating to reflux. After the reaction was finished, the reaction solution was concentrated in vacuo, 500 g of a 10 weight% aqueous solution of citric acid was added to the resulting residue and the mixture was extracted with 2,000 ml of toluene. The organic layer was successively washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated in vacuo. n-Hexane (200 ml) was added to the resulting residue and the resulting solid was filtered off and washed with 400 ml of cold n-hexane to give 77 g of the title compound as light brown powder (yield: 60%). Melting point: 92 to 93C Rf value: 0.56 (n-hexane: ethyl acetate = 4:1 (v/v)) Mass spectrum (EI, m/z): 313, 315 (M+) 1H-NMR spectrum (CDCl3, delta ppm): 1.36 (brs, 9H), 1.59 (s, 6H), 4.90 (brs, 1H), 7.24-7.29 (m, 2H), 7.39-7.45 (m, 2H)
60% (Reference Example 4) Synthesis of 1-bromo-4-(1-tert-butoxycarbonylamino-1-methylethyl)benzene (Reference compound 4-1) 260 g (600 mmol) of [bis(trifluoroacetoxy)iodo]benzene was added to a solution of 99 g (410 mmol) of 4-(1-aminocarbonyl-1-methylethyl)-1-bromobenzene (Reference compound 2) in 1000 ml of tert-butanol at room temperature in an argon stream with stirring, and the mixture was stirred for 30 minutes under a condition of heating to reflux. Then, 100 ml (1200 mmol) of pyridine was added thereto and the mixture was stirred for 1 hour under a condition of heating to reflux. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and 500 g of an aqueous solution of 10% by weight of citric acid was added to the resulting residue, and then the mixture was extracted with 2000 ml of toluene. The organic layer was successively washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. 200 ml of n-hexane was added to the resulting residue and the resulting solid was collected by filtration and washed with 400 ml of cold n-hexane, whereby 77 g of the title compound was obtained as light brown powder (yield: 60%). Melting point: 92 to 93C Rf value: 0.56 (n-hexane: ethyl acetate = 4: 1 (v/v)) Mass spectrum (EI, m/z): 313, 315 (M+) 1H-NMR spectrum (CDCl3, deltappm): 1.36 (brs, 9H), 1.59 (s, 6H), 4.90 (brs, 1H), 7.24-7.29 (m, 2H), 7.39-7.45 (m, 2H)
  • 3
  • [ 2712-78-9 ]
  • [ 1391728-13-4 ]
 

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