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Structure of 827614-70-0

Chemical Structure| 827614-70-0

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Product Details of [ 827614-70-0 ]

CAS No. :827614-70-0
Formula : C12H14BF3O2
M.W : 258.04
SMILES Code : CC1(C)OB(OC1(C)C)C1=CC(F)=C(F)C(F)=C1
MDL No. :MFCD05663885
InChI Key :VFCTUUBAONBDJU-UHFFFAOYSA-N
Pubchem ID :2760701

Safety of [ 827614-70-0 ]

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

Computational Chemistry of [ 827614-70-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 6
Fraction Csp3 0.5
Num. rotatable bonds 1
Num. H-bond acceptors 5.0
Num. H-bond donors 0.0
Molar Refractivity 62.79
TPSA ?

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

18.46 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

3.21
Log Po/w (WLOGP)?

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

3.66
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.

2.95
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

3.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.58

Water Solubility

Log S (ESOL):?

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

-3.64
Solubility 0.0587 mg/ml ; 0.000228 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.

-3.27
Solubility 0.139 mg/ml ; 0.000537 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 0.00375 mg/ml ; 0.0000145 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

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

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

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.

-5.59 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)

3.01

Application In Synthesis of [ 827614-70-0 ]

* 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 [ 827614-70-0 ]

[ 827614-70-0 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 2404-35-5 ]
  • [ 827614-70-0 ]
  • [ 1146593-95-4 ]
  • 2
  • [ 827614-70-0 ]
  • [ 594-19-4 ]
  • Li[(F3C6H2)(tert-butyl)B((pinacol)(-2H))] [ No CAS ]
  • 3
  • [ 827614-70-0 ]
  • 9,10-dibromo-2,3,6,7-tetrakis(4-tert-butylphenyl)anthracene [ No CAS ]
  • [ 1313373-82-8 ]
  • 4
  • [ 138526-69-9 ]
  • [ 827614-70-0 ]
  • 5
  • [ 76-09-5 ]
  • [ 1338809-70-3 ]
  • [ 827614-70-0 ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 20℃; for 0.5h; General procedure: General procedure: The synthetic procedure for pentafluorophenyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonate (a) is presented as an example (Scheme 1). 2,2'-Bis(1,3,2-benzodioxaborole) (cat2B2, 262 mg, 1.10 mmol), PdCl2(dppf) (25 mg, 0.030 mmol), AcOK (294 mg, 3.0 mmol), pentafluorophenyl 4-bromobenzenesulfonate (403 mg, 1.0 mmol), and EtOH (6.0 mL) were charged in a reaction vessel under an Ar atmosphere. The resulting mixture was stirred for 2 h at 80 C. After cooling to room temperature, pinacol (260 mg, 2.20 mmol) was added to the mixture. The mixture was further stirred for 30 min at room temperature. H2O and n-hexane were added to the mixture and the product was extracted into the organic layer. After drying the organic layer with anhydrous MgSO4, solids were removed by filtration. The filtrate was concentrated. The product was obtained as a white solid by Kugelrohr distillation.
  • 7
  • [ 827614-70-0 ]
  • 3',4',5'-trifluoro-4-methoxy-[1,1'-biphenyl]-3-ol [ No CAS ]
  • 8
  • [ 827614-70-0 ]
  • [ 1287221-38-8 ]
  • C19H20BF3O3 [ No CAS ]
  • 9
  • [ 827614-70-0 ]
  • C38H38ClF3N4O5S [ No CAS ]
  • 10
  • [ 827614-70-0 ]
  • (2R)-2-[(5Sa)-5-{3-chloro-2-methyl-4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}-6-(3,4,5-trifluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}-3-(2-methoxyphenyl)propanoic acid [ No CAS ]
  • 11
  • [ 827614-70-0 ]
  • ethyl (2R)-2-[(5Sa)-5-(3-chloro-4-hydroxy-2-methylphenyl)-6-iodothieno[2,3-d]pyrimidin-4-yl]oxy-3-(2-methoxyphenyl)propanoate [ No CAS ]
  • C31H24ClF3N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: 2.5 eq. of the appropriate boronic acid was dissolved in dry dioxane (5 mL/mmol Preparation 25), then 2.5 eq pinaeol and dry acidic Amberlyst (100 mg/mmol boronie acid) were added and the mixture was stined at room temperature overnight, then it was filtered (if the appropriate boronic ester was available, then it was dissolved in dioxane (5 mL /rmnol Preparation 25) and this solution was used instead of the filtrate). 1 eq. ethyl(2B)-2-[(5S0)-5-(3 -ehloro-4-hydroxy-2-methyl-phenyl)-6-iodo-thieno[2,3-d]pyrimidin-4-yl]oxy-3-(2-methoxyphenyl)propanoate (Preparation 25), 0.1 eq. PdC12 x dppf, 2.5 eq. Cs2CO3 and water (2.5 mL/mmol) were added to the filtrate and the mixture was heated under nitrogen at 110C in a microwave reactor until no further conversion was observed. Then it was diluted with brine, neutralized with 2 M HCI, and extracted with DCM. Thecombined organic phases were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified via flash chromatography using heptane and EtOAc as eluents.
  • 12
  • (E)-2-(4-bromostyryl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione [ No CAS ]
  • [ 827614-70-0 ]
  • trans-4,4,5,5-tetramethyl-2-(2-(3',4',5'-trifluoro-[1,1'-biphenyl]-4-yl)vinyl)-1,3,2-dioxaborolane [ No CAS ]
  • 13
  • [ 2367-82-0 ]
  • [ 73183-34-3 ]
  • [ 827614-70-0 ]
  • 4,4,5,5-tetramethyl-2-(2,3,5-trifluorophenyl)-1,3,2-dioxaborolane [ No CAS ]
  • 14
  • [ 827614-70-0 ]
  • 1-(2,3-dihydro-1H-inden-2-yl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]
  • 1-(2,3-dihydro-1H-inden-2-yl)-3-(3,4,5-trifluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]
  • 15
  • [ 1489-53-8 ]
  • [ 73183-34-3 ]
  • [ 881401-96-3 ]
  • [ 827614-70-0 ]
  • 16
  • [ 827614-70-0 ]
  • [ 75344-77-3 ]
  • 3',4',5'-trifluoro-2,6-dimethyl-[1,1'-biphenyl]-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.2% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 85℃;Inert atmosphere; Under a nitrogen atmosphere, Add 2.52 g (12 mmol) to a 250 ml three-neck round bottom reaction flask4-bromo-3,5-dimethylbenzonitrile and 2.814 g (16 mmol) of 4,4,5,5-tetramethyl-2-(3,4,5-trifluorophenyl)-1,3, 2-dioxaborolan,Then, 120 ml of toluene, 50 ml of ethanol was added, and then 40 ml of a saturated solution of potassium carbonate (2 mol/L) was added and stirred. After 15 minutes of aeration, tetrakis(triphenylphosphine)palladium 100 mg (0.087 mmol) was added and aeration was continued for 15 minutes. The reaction system was heated to 85 C and stirred at reflux overnight.After the reaction was stopped to return to room temperature, the solvent of the reaction system was removed by rotary evaporation. The reaction system was extracted with dichloromethane and washed three times with deionized water and three times with brine.The product was purified by column chromatography using a mixture of petroleum ether and dichloromethane in a ratio of 3:1.Finally, 2.8 g of a white solid 3',4',5'-trifluoro-2,6-dimethyl-[1,1'-biphenyl]-4-carbonitrile (intermediate product) was obtained.The yield was 89.2%.
  • 17
  • [ 827614-70-0 ]
  • 3,7-bis(4-bromophenyl)-1,5-didodecyldipyrrolo-[2,3-b:2',3'-e]pyrazine-2,6(1H,5H)-dione [ No CAS ]
  • 1,5-didodecyl-3,7-bis(3',4',5'-trifluorobiphenyl-4-yl)dipyrrolo[2,3-b:2',3'-e]pyrazine-2,6(1H,5H)-dione [ No CAS ]
  • 18
  • [ 1100243-35-3 ]
  • [ 827614-70-0 ]
  • N,N'-bis(2-octyldodecyl)-2,6-bis(3,4,5-trifluorophenyl)naphthalene-1,8,4,5-bis(dicarboximide) [ No CAS ]
  • 19
  • [ 1211417-77-4 ]
  • [ 827614-70-0 ]
  • (2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)(1,3-dimethyl-1H-imidazol-3-ium-2-yl)dihydroborate [ No CAS ]
 

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