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Chemical Structure| 14533-84-7 Chemical Structure| 14533-84-7

Structure of 14533-84-7

Chemical Structure| 14533-84-7

Pentafluorophenyl trifluoroacetate

CAS No.: 14533-84-7

4.5 *For Research Use Only !

Cat. No.: A314355 Purity: 98%

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Product Details of [ 14533-84-7 ]

CAS No. :14533-84-7
Formula : C8F8O2
M.W : 280.07
SMILES Code : O=C(OC1=C(F)C(F)=C(F)C(F)=C1F)C(F)(F)F
MDL No. :MFCD00134438
InChI Key :VCQURUZYYSOUHP-UHFFFAOYSA-N
Pubchem ID :4327891

Safety of [ 14533-84-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
Class:3
UN#:3272
Packing Group:

Computational Chemistry of [ 14533-84-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 3
Num. H-bond acceptors 10.0
Num. H-bond donors 0.0
Molar Refractivity 37.92
TPSA ?

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

26.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.9
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

3.29
Log Po/w (WLOGP)?

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

6.21
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.

4.47
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

4.57
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.09

Water Solubility

Log S (ESOL):?

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

-3.7
Solubility 0.0562 mg/ml ; 0.000201 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.

-3.52
Solubility 0.0851 mg/ml ; 0.000304 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

-4.37
Solubility 0.012 mg/ml ; 0.000043 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

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.

-5.67 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

1.0
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

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

3.0 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)

1.91

Application In Synthesis of [ 14533-84-7 ]

* 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 [ 14533-84-7 ]

[ 14533-84-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 69907-67-1 ]
  • [ 14533-84-7 ]
  • pentafluorophenyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate [ No CAS ]
  • 2
  • [ 14533-84-7 ]
  • [ 103213-32-7 ]
  • [ 115520-21-3 ]
  • 3
  • [ 14533-84-7 ]
  • [ 58-85-5 ]
  • [ 120550-35-8 ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine; In N,N-dimethyl-formamide; at 0 - 70℃; for 1h; D-Biotin (1.00 g, 4.09 mmol) was dissolved in 20 mL DMF at 70 C and allowed to cool to rt. TEA (0.83g, 1.14 mL, 8.19 mmol) was added, followed by pentafluorophenyl trifluoroacetate (1.60 g, 0.98 mL, 5.73 mmol). The reaction was allowed to stir for 1 h at 0 C and became pink. Solvent was reduced to 1 mL in vacuo and the crude material was triturated with cold diethyl ether. The pFp ester product was recovered as a white solid (1.54 g, 96%). Biotin-pFp ester (1.00 g, 2.44 mmol) was dissolved in 10 mL DMF and cooled to 0 C. A flask containing a suspension of NaBH4 (3.4 mmol) in dry DMF (5 mL) was also cooled to 0 C. The pFp-ester was transferred dropwise via a cannula over 15 min and the mixture was stirred at 0 C. The reaction was followed by TLC and upon completion the cold mixture was acidified with 1 N HC1 and reduced to 1 mL in vacuo. The residue was triturated with cold diethyl ether and the product alcohol was recovered as a white solid (0.528 g, 94%). The alcohol (0.528 g, 2.29 mmol) and TEA (0.39 ml, 1.2 eq) were dissolved in DMF (10 mL) and added dropwise to a stirred solution of 4-nitrophenyl chloroformate (4-NCF, 1.38 g, 6.87 mmol, 3.0 eq) in DMF (10 mL) over a period of 1 h at -10C. The reaction mixture was allowed to warm to rt, stirred overnight, and subsequently and reduced to 1 mL in vacuo. The residue was triturated with cold diethyl ether. The nitrophenol carbonate product was recovered as a white solid (0.96 g, 95%). Fmoc-L-Lys-OH (1.03 g, 2.83 mmol, 1.3 eq.) was suspended under argon in anhydrous DMF (10 ml) containing DiPEA (0.50 ml, 1.3 eq.). To this white suspension, a clear solution of the nitrophenol-carbonate (2.18 mmol, 1.0 eq.) in anhydrous DMF (10 mL) was added drop wise under argon at rt over a period of 2 h. The reaction mixture was stirred for additional 4 h at rt, before the solution as acidified to pH 2 with 1 N HC1. All volatiles were evaporated under reduced pressure and the residue was triturated with cold diethyl ether. The crude product was purified by column chromatography (DCM : MeOH 95 : 5 v/v) to give the Fmoc-protected ncAA as a white solid. The Fmoc- protected ncAA was dissolved in 20% piperidine in DMF (5 ml) and stirred for 1 h at r.t.. All volatiles were removed under reduced pressure and the residue was triturated with cold diethyl ether. Drying of the residue in vaccuum yield the pure ncAA as a white powder (0.622 g, 71 %). 1H-NMR (D6-DMSO, 400 MHz): delta = 1.30-1.45 (m, 6H), 1.50-1.65 (m, 4H), 1.85 (m, 2H), 2.65 (d, J = 12.2 Hz, 1H), 2.84 (dd, J= 5.0 Hz, J= 12.2 Hz, 1H), 2.95 (m, 2H), 3.13 (m, 1H), 3.42 (m, 1H), 3.66 (m, 1H), 3.85 (dd, J= 13.8 Hz, J = 1.0 Hz 1H), 3.93 (t, J= 7.5 Hz, 2H), 4.17 (dd, J= 8.2 Hz, J= 7.3 Hz, 1H), 4.35 (dd, J= 8.1 Hz, J= 7.2 Hz, 1H), 7.11 (t, J= 5.4 Hz, 1H), 8.50 (br, 3H), 8.53 (br, 1H), 8.68 (br, 1H).13C-NMR (D6-DMSO, 100 MHz): 13C-NMR (CDCI3, 100 MHz): delta = 171.44, 163.29, 156.82, 64.00, 61.61, 60.35, 59.79, 55.95, 52.28, 39.10, 30.05, 29.35, 29.02, 28.78, 28,73, 25.91, 22.05. HR-MS (C17H31N4O5S): calculated: 403.20097, found: 403.20159.
81% Biotin (5 g; 23.1 mmol; 1.0 eq) is suspended in anhydrous DMF (50 ml) and pyridine (2.07 ml; 25.4 mmol; 1.1 eq). After stirring for 5 minutes, pentafluorophenyl trifluoroacetate (PFP-TFA: 4.621 ml, i.e. 7.50 g; 25.4 mmol; 1.1 eq) is added. After stirring for one night, the reaction is finished, and the solvents are evaporated on the rotary evaporator. The evaporation residue is taken up in 100 ml of ethyl ether to suspend it, then filtered off on a fritted filter, and the cake is rinsed with a minimum of ether. Note: in the TLC a small trace of biotin is observed, but that will have no impact on what follows. m=7.106 g. Yield: 81%. TLC eluent: DCM/MeOH: 90/10.
  • 4
  • [ 14533-84-7 ]
  • [ 169396-92-3 ]
  • pentafluorophenyl N-<2-(N-9-fluorenylmethoxycarbonyl)aminoethyl>-N-<(thymin-1-yl)acetyl>glycinate [ No CAS ]
  • 5
  • [ 14533-84-7 ]
  • [ 174623-07-5 ]
  • C18H7F5O3S [ No CAS ]
  • 6
  • [ 14533-84-7 ]
  • [ 210366-15-7 ]
  • pentafluorophenyl-1-benzyloxy-2(1H)-pyridinone-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.5h; A solution of 22 (0.40 g, 1.6 mmol) in dry N,N-dimethylformamide(4 mL) was added dropwise to a solution of pentafluorophenyltrifluoroacetate (0.59 g, 2.1 mmol) and pyridine (0.14 g,1.8 mmol) in dry N,N-dimethylformamide at 0 C, before stirring atambient temperature for 1.5 h. The mixture was then diluted with ethylacetate (300 mL) and washed with aqueous hydrochloric acid (0.1 M;3×50 mL), aqueous sodium hydrogen carbonate (5%; 3× 50 mL) andbrine (50 mL) before drying the organics with magnesium sulfate, filtrationand solvent removal in vacuo to yield the crude product as acrystalline cream solid was used without purification. deltaH (400 MHz;CDCl3; Me4Si) 5.41 (2H, s) 6.96 (1H, dd, J 1.8, 6.9 Hz) 7.01 (1H, dd, J1.4, 9.2 Hz) 7.35-7.39 (3H, m) 7.42 (1H, dd, J 6.9, 9.2 Hz) 7.52-7.54(2H, m); deltaC (100 MHz) 78.9, 111.4, 124.2 (m), 128.6, 129.4, 130.2,133.1, 135.2, 136.9 (m), 137.0, 138.8 (m), 139.3 (m), 139.9 (m), 141.4(m), 142.4 (m), 155.2, 158.9, 162.9; (+)-ESI-MS: m/z 433.89(M + Na+).
 

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