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Chemical Structure| 764-52-3 Chemical Structure| 764-52-3

Structure of 764-52-3

Chemical Structure| 764-52-3

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Product Details of [ 764-52-3 ]

CAS No. :764-52-3
Formula : C5H8F3NO2S
M.W : 203.18
SMILES Code : N[C@@H](CCSC(F)(F)F)C(O)=O
MDL No. :MFCD07636752
InChI Key :YLJLTSVBCXYTQK-VKHMYHEASA-N
Pubchem ID :165196

Safety of [ 764-52-3 ]

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

Computational Chemistry of [ 764-52-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 0.8
Num. rotatable bonds 5
Num. H-bond acceptors 6.0
Num. H-bond donors 2.0
Molar Refractivity 38.41
TPSA ?

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

88.62 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.23
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

-0.66
Log Po/w (WLOGP)?

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

2.3
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.

-1.64
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

0.78
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.4

Water Solubility

Log S (ESOL):?

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

-0.35
Solubility 89.9 mg/ml ; 0.443 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-0.73
Solubility 38.1 mg/ml ; 0.187 mol/l
Class?

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

Very 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

-0.76
Solubility 35.6 mg/ml ; 0.175 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

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.

-8.01 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

0.0 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)

2.51

Application In Synthesis of [ 764-52-3 ]

* 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 [ 764-52-3 ]

[ 764-52-3 ] Synthesis Path-Downstream   1~10

  • 1
  • N-acetyltrifluoromethylhomocysteine [ No CAS ]
  • [ 764-52-3 ]
  • 2
  • [ 24424-99-5 ]
  • [ 764-52-3 ]
  • [ 201870-90-8 ]
YieldReaction ConditionsOperation in experiment
39% With sodium hydroxide; In 1,4-dioxane; at 20℃; for 27.0h;Cooling with ice; Synthesis Example 2N-Boc-<strong>[764-52-3]trifluoromethionine</strong> (sk-269); Trifluoromethionine (3.3 g, 0.016 mol) was dissolved in 1.25 N NaOH (12.7 ml), and 1,4-dioxane (9.6 ml) was further added. Boc2O (3.7 g) dissolved in 1,4-dioxane (3.9 ml) was added dropwise in an ice bath. The mixture was stirred in the ice bath for 3 hours and allowed to react for 24 hours at room temperature. After completion of the reaction, 1,4-dioxane was evaporated, and 1 M KHSO4 (16 ml) was added thereto, followed by extraction with ethyl acetate. The extract was washed with water (6 ml) and brine (1 ml) and dried with Na2SO4. The solvent was distilled off under reduced pressure, thereby the product (1.9 g, 39%) was obtained.M.W.: 303.30Rf=0.25 (hexane/ethyl acetate=60/40)1H-NMR (CDCl3, 200 MHz) delta: 1.46 (9H, s), 2.05-2.12 (1H, m), 2.31-2.34 (1H, m), 2.98 (2H, t, J=7.6 Hz), 4.30-4.42 (1H, br), 8.45 (1H, br)19F-NMR (CDCl3, 188 MHz) delta: -42.0 (s)
  • 3
  • [ 82911-69-1 ]
  • [ 764-52-3 ]
  • Fmoc-S-trifluoromethionine [ No CAS ]
  • 7
  • [ 626-72-2 ]
  • [ 2314-97-8 ]
  • [ 764-52-3 ]
YieldReaction ConditionsOperation in experiment
93% FIRST EMBODIMENTIn a 500-ml three-necked flask equipped with a liquid-ammonia cooling device, a glass stirring bar, a thermometer, and a septum rubber cap was placed 10.0 g (37.3 mmol) of L-homocystine, followed by thorough purging of the flask with nitrogen. After cooling the flask to -78 C., ammonia which had been dried by passing through a KOH tube was liquefied in the liquid-ammonia cooling device cooled on a dry ice-acetone bath, and the liquid ammonia was added in a volume of about 100 ml to L-homocystine, followed by stirring. Next, 3.58 g (156 mmol) of metallic sodium was gradually added while avoiding rise of the temperature of the mixture above -35 C. The solution (mixture) became dark blue in this step. Next, 18.2 g (93.3 mmol) of trifluoromethyl iodide weighed using a balloon was added, the mixture was stirred on a bath at -78 C. for 20 minutes, from which ammonia was gradually evaporated, the residue was dissolved in ultrapure water, and the solution was placed on an ion exchange resin DOWEX-50X8 which had been treated with hydrochloric acid. After passing a sufficient amount of ultrapure water, elution with a 2% aqueous ammonia solution was performed, and thereby yielded 14.1 g of target L-trifluoromethionine in a yield of 93%.1H-NMR (D2O, 200 MHz) delta: 2.07-2.37 (m, 2H) , 3.01 (t, 2H, J=7.6 Hz), 4.03 (t, 1H, J=6.6 Hz)19F-NMR (D2O, 188 MHz) delta: -41.3 (s)
  • 8
  • [ 943925-89-1 ]
  • [ 62-53-3 ]
  • [ 764-52-3 ]
  • 9
  • [ 764-52-3 ]
  • [ 600-18-0 ]
  • [ 1493-15-8 ]
  • 10
  • [ 1445869-56-6 ]
  • [ 6018-89-9 ]
  • [ 764-52-3 ]
  • C30H30F3N3NiO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate; In ethanol; at 60 - 70℃; General procedure: To a flask containing ethanol solution of reagent 3 (1 equiv.), Ni(OAc)2·4H2O (4 equiv.), racemic amino acid (2.0 equiv.), was added K2CO3 (15 equiv.), and the reaction mixture was stirred at 60-70 C. The progress of the reaction was monitored by TLC and upon completion (consumption of the reagent 3), the reaction mixture was poured into ice water. The target product was extracted several times with CH2Cl2. The combined organic layer was dried over anhydrous MgSO4 and evaporated under vacuum. After evaporation of the solvents and silica-gel column chromatography, the target complexes 5a-c and 6a,b were obtained in diastereomerically pure form.
 

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