Home Cart Sign in  
Chemical Structure| 313545-34-5 Chemical Structure| 313545-34-5

Structure of 313545-34-5

Chemical Structure| 313545-34-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 313545-34-5 ]

CAS No. :313545-34-5
Formula : C7H5BF4O2
M.W : 207.92
SMILES Code : OB(O)C1=C(F)C=CC=C1C(F)(F)F
MDL No. :MFCD07781239
InChI Key :TXBRJTKFAYXKMV-UHFFFAOYSA-N
Pubchem ID :16217168

Safety of [ 313545-34-5 ]

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

Computational Chemistry of [ 313545-34-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 2
Num. H-bond acceptors 6.0
Num. H-bond donors 2.0
Molar Refractivity 41.23
TPSA ?

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

40.46 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

1.81
Log Po/w (WLOGP)?

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

2.1
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.

1.8
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

0.76
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.29

Water Solubility

Log S (ESOL):?

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

-2.45
Solubility 0.73 mg/ml ; 0.00351 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.

-2.28
Solubility 1.09 mg/ml ; 0.00526 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

-2.46
Solubility 0.721 mg/ml ; 0.00347 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.

-6.28 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

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)

2.0

Application In Synthesis of [ 313545-34-5 ]

* 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 [ 313545-34-5 ]

[ 313545-34-5 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 313545-34-5 ]
  • [ 1255710-27-0 ]
  • [ 1255710-29-2 ]
  • [ 1255710-28-1 ]
YieldReaction ConditionsOperation in experiment
30% With sodium carbonate;dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In 1,2-dimethoxyethane; at 95℃; for 18.0h; A solution of 5-bromo-2-[2-(4,4-difluoro-cyclohexyl)-vinyl]-1 H- benzimidazole (0.030 g, 0.088 mmol, prepared as in STEP F above), 2-fluoro- 6-thfluoromethylphenyl boronic acid (0.040 g, 0.19 mmol), 1 ,1-bis(di-t-butyl- phosphinoferrocene palladium chloride (0.012 g, 0.018 mmol) in dimethoxyethane (2 ml_) and 2M sodium carbonate (1.0 ml_, 2 mmol) was stirred at 95C for 18 h. The resulting solution was cooled to room temperature and poured into a solution of ethyl acetate and water (1 :1 , 50 ml_). The layers were separated. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica using ethyl acetate/hexanes 3:7 as eluent to yield 2-[2-(4,4-difluoro-cyclohexyl)-vinyl]-5-(2- fluoro-6-thfluoromethyl-phenyl)-1 H-benzimidazole.1H-NMR (400 MHz, DMSO d6) delta (ppm) 7.56-7.64 (m, 2H) 7.44-7.52 (m, 2H) 7.32-7.38 (m, 1 H) 7.14-7.18 (m, 1 H) 6.68-6.78 (m, 1 H) 6.47-6.56 (m, 1 H) 2.32-2.40 (m, 1 H) 2.10-2.20 (m, 2H) 1.80-1.96 (m, 6H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C22Hi8F6N2: 407.1 (M + H), Found 407.3 and 2- [2-(4-fluoro-cyclohex-3-enyl)-vinyl]-5-(2-thfluoromethyl-phenyl)-1 H- benzimidazole (0.50 g, 30%). 1H-NMR (400 MHz, CDCI3) delta (ppm): 7.70-7.76 (m, 1 H) 7.40-7.56 (m, 4H) 7.38-7.40 (m, 1 H) 7.16-7.22 (m, 1 H) 6.74-6.82 (m, 1 H) 6.48-6.56 (m, 1 H) 5.14-5.23 (m, 1 H) 2.44-2.56 (m, 1 H) 2.16-2.30 (m, 3H) 1.90-2.04 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C22Hi8F4N2: 387.2 (M + H), Found 387.2.
  • 2
  • [ 313545-34-5 ]
  • [ 1255709-90-0 ]
  • [ 1365107-89-6 ]
  • 3
  • [ 313545-34-5 ]
  • [ 1586044-82-7 ]
  • [ 1586041-16-8 ]
YieldReaction ConditionsOperation in experiment
Example 278 5-amino-N-(5-((2S,5R,6R)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2-fluoro-6-(trifluoromethyl)phenyl)thiazole-4-carboxamide 278 Following the procedure for Example 101 starting from tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6R)-5-(tert-butoxycarbonylamino)-6-fluoro-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate (Intermediate 88), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with <strong>[313545-34-5](2-fluoro-6-(trifluoromethyl)phenyl)boronic acid</strong> gave 278. 1H NMR (400 MHz, DMSO-d6) delta 9.19 (s, 1H), 7.85-7.69 (m, 4H), 7.47 (s, 2H), 5.03-4.74 (m, 2H), 4.00-3.86 (m, 2H), 3.74 (s, 3H), 2.13 (ddt, J=14.4, 6.1, 2.8 Hz, 1H), 2.01-1.61 (m, 3H). LCMS (ES+) m/z 517 (M+1).
  • 4
  • [ 313545-34-5 ]
  • [ 1586044-98-5 ]
  • [ 1586041-68-0 ]
YieldReaction ConditionsOperation in experiment
Example 331 5-amino-N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2-fluoro-6-(trifluoromethyl)phenyl)thiazole-4-carboxamide 331 Following the procedure for Example 101 starting from tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6S)-5-(tert-butoxycarbonylamino)-6-fluoro-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate (Intermediate 95), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with <strong>[313545-34-5](2-fluoro-6-(trifluoromethyl)phenyl)boronic acid</strong> gave 331. 1H NMR (400 MHz, DMSO-d6) delta 9.18 (s, 1H), 7.81-7.68 (m, 3H), 7.42 (s, 2H), 4.78-4.68 (m, 1H), 4.45-4.26 (m, 1H), 4.14-3.86 (m, 2H), 3.76 (s, 3H), 2.07-1.97 (m, 1H), 1.88-1.76 (m, 1H), 1.76-1.65 (m, 2H). LCMS (ES+) m/z 517 (M+1).
  • 5
  • [ 313545-34-5 ]
  • [ 1586045-02-4 ]
  • [ 1586041-17-9 ]
YieldReaction ConditionsOperation in experiment
Example 279 5-amino-N-(5-((2S,5R,6R)-5-amino-6-methoxyoxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2-fluoro-6-(trifluoromethyl)phenyl)thiazole-4-carboxamide 279 Following the procedure for Example 101 starting from tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6R)-5-(tert-butoxycarbonylamino)-6-methoxy-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate (Intermediate 98), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with <strong>[313545-34-5](2-fluoro-6-(trifluoromethyl)phenyl)boronic acid</strong> gave 279. 1H NMR (400 MHz, DMSO-d6) delta 9.41 (s, 1H), 7.90 (s, 1H), 7.84-7.68 (m, 3H), 7.47 (s, 2H), 5.03 (t, J=5.2 Hz, 1H), 3.71-3.52 (m, 5H), 3.29-3.13 (m, 2H), 2.72 (s, 3H), 2.48-2.40 (m, 1H), 1.63-1.47 (m, 5H). LCMS (ES+) m/z 529 (M+1).
  • 6
  • [ 313545-34-5 ]
  • [ 53857-57-1 ]
  • [ 1613505-02-4 ]
  • 7
  • [ 313545-34-5 ]
  • [ 138647-49-1 ]
  • tert-butyl 4-(2-fluoro-6-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; at 80℃; for 4.0h; A mixture of tert-butyl 4- (( (trifluoromethyl) sulfonyl) oxy) - 5, 6-dihydropyridine- 1 (2H) -carboxylate (2, 1.20 g, 3.62 mmol) , and 6- fluoro- (2-trifluoromethyl) phenyl boronic acid (0.528 g, 2.53 mmol), Pd(PPh3)4 (0.292 g, 0.253 mmol), and 2 M Na2C03 (20 mL) in DME (30 mL) was heated to 80 C for 4 h. The mixture cooled to ambient temperature, was diluted with EtOAc (50 mL) , and filtered through a Celite pad. The organic filtrate was washed with saturated sodium bicarbonate solution (2 chi 30 mL) , H2O (30 ml) , and concentrated to under reduced pressure. The resulting residue was chromatographed over silica gel (Isco CombiFlash Companion unit, 40 g Redisep column, 0% to 10% EtOAc in hexanes) to provide tert-butyl 4- (2-fluoro-6- (trifluoromethyl) phenyl) -5, 6-dihydropyridine-l (2H) -carboxylate (21) as a clear oil (0.479 g, 39%) : XH NMR (300 MHz, DMSO-d6) delta 7.66-7.51 (m, 3H) , 5.68 (s, 1H) , 4.04-3.82 (m, 2H) , 3.67-3.39 (m, 2H) , 2.39-2.02 (m, 2H) , 1.43 (s, 9H) .
  • 8
  • [ 313545-34-5 ]
  • tert-butyl 2-(6-methylene-3,7-dioxo-4-(2,4,6-trimethoxybenzyl)-1,4-diazepan-1-yl)acetate [ No CAS ]
  • tert-butyl 2-(6-(2-fluoro-6-(trifluoromethyl)benzyl)-3,7-dioxo-4-(2,4,6-trimethoxybenzyl)-1,4-diazepan-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With [Rh(OH)(cod)]2; In 1,4-dioxane; water; at 80 - 100℃; for 2.0h; General procedure: To a solution of 34 15 (260mg, 0.598mmol) in 117 dioxane/114 H2O (10/1) (3 ml) were added 118 2-cyanophenylboronic acid (172mg, 1.17mmol) and 119 hydroxy(1,5-cyclooctadiene)rhodium (I) dimer (27.3mg, 0.060mmol), and the mixture was stirred at 80C for 2h. The reaction mixture was diluted with AcOEt, and successively washed with sat. KHSO4 aq., sat. NaHCO3 aq., and brine. The organic layer was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent A: hexane/AcOEt (1/1), eluent B: MeOH; A/B=95/5 to 90/10) to give the 120 title compound as a pale yellow solid (321mg, quant.).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 313545-34-5 ]

Fluorinated Building Blocks

Chemical Structure| 159020-59-4

A128097 [159020-59-4]

(3-Fluoro-5-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.86

Chemical Structure| 1021860-94-5

A100019 [1021860-94-5]

(4-Methyl-2-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.86

Chemical Structure| 153254-09-2

A287523 [153254-09-2]

2,4-Bis(trifluoromethyl)phenylboronic acid

Similarity: 0.86

Chemical Structure| 182344-16-7

A314331 [182344-16-7]

(4-Fluoro-2-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.85

Chemical Structure| 928053-97-8

A151728 [928053-97-8]

5-Fluoro-2-(trifluoromethyl)phenylboronic acid

Similarity: 0.82

Organoborons

Chemical Structure| 159020-59-4

A128097 [159020-59-4]

(3-Fluoro-5-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.86

Chemical Structure| 1021860-94-5

A100019 [1021860-94-5]

(4-Methyl-2-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.86

Chemical Structure| 153254-09-2

A287523 [153254-09-2]

2,4-Bis(trifluoromethyl)phenylboronic acid

Similarity: 0.86

Chemical Structure| 182344-16-7

A314331 [182344-16-7]

(4-Fluoro-2-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.85

Chemical Structure| 928053-97-8

A151728 [928053-97-8]

5-Fluoro-2-(trifluoromethyl)phenylboronic acid

Similarity: 0.82

Aryls

Chemical Structure| 159020-59-4

A128097 [159020-59-4]

(3-Fluoro-5-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.86

Chemical Structure| 1021860-94-5

A100019 [1021860-94-5]

(4-Methyl-2-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.86

Chemical Structure| 153254-09-2

A287523 [153254-09-2]

2,4-Bis(trifluoromethyl)phenylboronic acid

Similarity: 0.86

Chemical Structure| 182344-16-7

A314331 [182344-16-7]

(4-Fluoro-2-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.85

Chemical Structure| 928053-97-8

A151728 [928053-97-8]

5-Fluoro-2-(trifluoromethyl)phenylboronic acid

Similarity: 0.82

Trifluoromethyls

Chemical Structure| 159020-59-4

A128097 [159020-59-4]

(3-Fluoro-5-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.86

Chemical Structure| 1021860-94-5

A100019 [1021860-94-5]

(4-Methyl-2-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.86

Chemical Structure| 153254-09-2

A287523 [153254-09-2]

2,4-Bis(trifluoromethyl)phenylboronic acid

Similarity: 0.86

Chemical Structure| 182344-16-7

A314331 [182344-16-7]

(4-Fluoro-2-(trifluoromethyl)phenyl)boronic acid

Similarity: 0.85

Chemical Structure| 928053-97-8

A151728 [928053-97-8]

5-Fluoro-2-(trifluoromethyl)phenylboronic acid

Similarity: 0.82