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Chemical Structure| 1255206-73-5 Chemical Structure| 1255206-73-5

Structure of 1255206-73-5

Chemical Structure| 1255206-73-5

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Product Details of [ 1255206-73-5 ]

CAS No. :1255206-73-5
Formula : C10H7F3O5S
M.W : 296.22
SMILES Code : O=S(C(F)(F)F)(OC1=C(C)C2=C(C(OC2)=O)C=C1)=O
MDL No. :MFCD26793923
InChI Key :VEUQZWVGMYVTMY-UHFFFAOYSA-N
Pubchem ID :86647292

Safety of [ 1255206-73-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H318
Precautionary Statements:P264-P270-P280-P301+P312-P305+P351+P338-P310-P330-P501
Class:9
UN#:3077
Packing Group:

Computational Chemistry of [ 1255206-73-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 6
Fraction Csp3 0.3
Num. rotatable bonds 3
Num. H-bond acceptors 8.0
Num. H-bond donors 0.0
Molar Refractivity 56.38
TPSA ?

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

78.05 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.59
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

2.46
Log Po/w (WLOGP)?

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

4.08
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.

1.76
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

2.04
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.39

Water Solubility

Log S (ESOL):?

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

-3.26
Solubility 0.162 mg/ml ; 0.000547 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-3.74
Solubility 0.0535 mg/ml ; 0.000181 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

-3.51
Solubility 0.092 mg/ml ; 0.00031 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

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

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.

-6.36 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

0.0
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

2.0 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<0.0
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)

2.55

Application In Synthesis of [ 1255206-73-5 ]

* 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 [ 1255206-73-5 ]

[ 1255206-73-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1255206-73-5 ]
  • potassium vinyltrifluoroborate [ No CAS ]
  • [ 1255206-69-9 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 90℃;Inert atmosphere; 4-methyl-l-oxo-l,3-dihydroisobenzofuran- 5-yl trifluoromethanesulfonate (5.0 g, 16.88 mmol), potassium trifiuoro(vinyl)borate (4.52 g, 33.8 mmol), and PdCl2(dppf)-CH2Cl2 Adduct (0.689 g, 0.844 mmol) were placed in a reaction vessel, Ethanol (50 ml) was added to the mixture followed by triethylamine (4.71 ml, 33.8 mmol) and degassed with N2. The resulting mixture was heated over night at 90C. The reaction mixture was diluted with EtOAc and filtered through celite. The filtrate was evaporated to dryness and purified by silica gel column chromatography using (0-45)%> EtOAc/Hexanes as mobile phase and the title product was isolated as white solid. LC/MS [M+Hf = 175
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; at 90℃; for 12h;Inert atmosphere; To a degassed solution of 4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate (1 g, 3.38 mmol), TEA (0.941 mL, 6.75 mmol) and potassium vinyltrifluoroborate (0.904 g, 6.75 mmol) in EtOH (10 mL) was added Pd(dppf)C12 (0.247 g, 0.338 mmol) at 25C under N2 protection. The resulting mixture was heated to 90C for 12 h. The mixture was diluted with DCM and water, and filtered through a Celite pad. The filtrate was separated, and the aqueous phase was extracted with DCM. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated, and the crude product was purified by column chromatography on silica gel (eluting with 1-5% ethyl acetate in petroleum ether) to give 4-methyl -5-vinylisobenzofuran-1(3H)-one. MS (ESI) m/z 175.1 (M+H)
 

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