163266-02-2|4,4,4-Trifluoro-1-(o-tolyl)butane-1,3-dione| Ambeed

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Quality Control of [ 163266-02-2 ] Purity: 97% SDS Specification

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Product Details of [ 163266-02-2 ]

CAS No. :	163266-02-2
Formula :	C₁₁H₉F₃O₂
M.W :	230.18
SMILES Code :	O=C(C1=CC=CC=C1C)CC(C(F)(F)F)=O
MDL No. :	MFCD03420671
InChI Key :	NSWJGKUEKYWEEF-UHFFFAOYSA-N
Pubchem ID :	15772021

Safety of [ 163266-02-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H320-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 163266-02-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	6
Fraction Csp3	0.27
Num. rotatable bonds	4
Num. H-bond acceptors	5.0
Num. H-bond donors	0.0
Molar Refractivity	51.61
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	34.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.78
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.94
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.96
Log P_o/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.	2.1
Log P_o/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	3.48
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.85

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.13
Solubility	0.17 mg/ml ; 0.000736 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.	-3.32
Solubility	0.11 mg/ml ; 0.00048 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	-3.98
Solubility	0.0241 mg/ml ; 0.000105 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	Yes
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.	-5.62 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)	1.57

Application In Synthesis of [ 163266-02-2 ]

* 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 [ 163266-02-2 ]

[ 163266-02-2 ] Synthesis Path-Downstream 1~33

1
[ 17852-52-7 ]
[ 163266-02-2 ]
4-[5-(2-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; ethyl acetate; at 40 - 80℃; for 2.5h;	2) to 250mL three-necked flask followed by adding the above intermediates,60 ml of ethyl acetate,Purified water 60ml,After stirring and dissolving at 40 C, 10.2 g of p-hydrazinobenzenesulfonamide hydrochloride was added,After heating to 80 C for 2.5h under refluxing,The volume ratio of 1:10 ethyl acetate and petroleum ether mixture as developing solvent,TLC monitoring until the end of the reaction, and then cooled to precipitate a solid, filtered, washed with water,Dry to get crude product;3) The crude product was recrystallized from 10 times the amount of 95% ethanol solution,The temperature was raised to 65 C to dissolve the crude product,After filtration, the filtrate was further heated to 80 C for 1 h,Stop heating, stirring cooling crystallization,The crystal was stirred at 5 C for 1.5 hours,Thus, a purified product of 4- [5- (2-methylphenyl) -3- (trifluoromethyl) -1-hydro-pyrazol-1-yl] benzenesulfonamide was obtained.

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365.
[2]Patent: CN107011265,2017,A .Location in patent: Paragraph 0032; 0033; 0041; 0042; 0047; 0048; 0053; 0054.

2
[ 383-63-1 ]
[ 577-16-2 ]
[ 163266-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol; for 2h;Reflux;	General procedure: Referring to Scheme 1, to the appropriate acetophenone derivative (0.05 mol) and ethyltrifluoroacetate (0.075 mol) in methanol (20 mL), sodium methoxide solution (0.1 mol of Na + 15 mL ofCH3OH) was added dropwise at room temperature, and the mixture was refluxed for 2 h. After themethanol was evaporated under vacuum, the residue was dissolved in ethyl acetate (50 mL), washedwith 5% HCl (25 mL) and water (25 mL), and dried over sodium sulfate. After the solvent wasevaporated under vacuum, the corresponding compound II was obtained.

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365.
[2]Journal of Fluorine Chemistry,2002,vol. 118,p. 135 - 147.
[3]Journal of Fluorine Chemistry,2006,vol. 127,p. 780 - 786.
[4]Molecules,2016,vol. 21.
[5]Patent: CN107011265,2017,A .Location in patent: Paragraph 0030; 0031; 0039; 0040; 0045; 0046; 0051; 0052.
[6]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3406 - 3413.

3
[ 100-63-0 ]
[ 163266-02-2 ]
5-(2-methylphenyl)-1-phenyl-3-trifluoromethylpyrazole [ No CAS ]

References: [1]Journal of Fluorine Chemistry,2002,vol. 118,p. 135 - 147.

5
[ 577-16-2 ]
[ 163266-02-2 ]

Yield	Reaction Conditions	Operation in experiment
64%		1F-a 1-(2-Methylphenyl)-4,4,4-trifluorobutane-1,3-dione This intermediate was prepared from commercially available 2- methylacetophenone. The product obtained was a liquid which was isolated from the reaction mixture by extraction with a suitable solvent like Ethyl acetate. The evaporation of the solvent gave the diketo product in 64% yield which was used as such for the next step. IR (KBr) cm-1 at 1147 (aliphatic C=O), 1199 (CF3), 1458 (C-H) 1608 (aromatic C=O)

References: [1]Patent: US2001/47023,2001,A1 .

6
[ 100-63-0 ]
[ 163266-02-2 ]
5-(2-methylphenyl)-1-phenyl-3-trifluoromethylpyrazole [ No CAS ]

References: [1]International Journal of Chemical Kinetics,2008,vol. 40,p. 370 - 383.

7
[RuCl₂(As(C₆H₅)3)2]2 [ No CAS ]
[ 163266-02-2 ]
[RuCl(As(C₆H₅)3)2(C₁₁H₈O₂F₃)]2 [ No CAS ]

References: [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1995,vol. 34,p. 490 - 492.

8
ruthenium(II) bis(triphenylphosphine) dichloride [ No CAS ]
[ 163266-02-2 ]
[RuCl(P(C₆H₅)3)2(C₁₁H₈O₂F₃)]2 [ No CAS ]

References: [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1995,vol. 34,p. 490 - 492.

9
[ 163266-02-2 ]
2-fluoro-1-(o-tolyl)-2-(2-(p-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)ethanone [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 1277 - 1282.

10
[ 163266-02-2 ]
2,4,4,4-tetrafluoro-3,3-dihydroxy-1-o-tolylbutan-1-one [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 1277 - 1282.

11
[ 163266-02-2 ]
[ 703-42-4 ]

References: [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 1531 - 1535.

12
[ 163266-02-2 ]
guanidine salt [ No CAS ]
4-(2-methylphenyl)-6-trifluoromethyl-2-aminopyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium methylate; In methanol; for 6h;Reflux;	General procedure: Compounds III were synthesized according to the method given in [16]. To the solution of sodiummethoxide (0.09 mol of Na + 10 mL of CH3OH), guanidine carbonate (0.08 mol) was added, and themixture was refluxed for 30 min. The appropriate compound II (0.01 mol) was added, then reacted for6 h. Acetic acid was added dropwise to the solution till pH = 4-5 at 0-5 C. The reaction solution wasfiltered, and the filter cake was washed with water (15 mL 2). The crude product was recrystallized from methanol to give pure compound III-1 to III-22. The nuclear magnetic resonance (NMR), infrared(IR), and mass spectrum (MS) data were as follows:

References: [1]Molecules,2016,vol. 21.

13
[ 163266-02-2 ]
[ 41441-74-1 ]

References: [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 402 - 409.

14
[ 163266-02-2 ]
(Z)-3-rac-((1S,5R,6S)-2,2-dimethyl-6-phenyl-3-oxabicyclo[3.1.0]hexan-1-yl)-1-(o-tolyl)prop-2-en-1-one [ No CAS ]
(E)-3-rac-((1S,5R,6S)-2,2-dimethyl-6-phenyl-3-oxabicyclo[3.1.0]hexan-1-yl)-1-(o-tolyl)prop-2-en-1-one [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 402 - 409.

15
[ 407-38-5 ]
[ 577-16-2 ]
[ 163266-02-2 ]

References: [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 402 - 409.

16
[ 6018-41-3 ]
[ 163266-02-2 ]
methyl 3-(2-methylbenzoyl)-4-(trifluoromethyl)benzoate [ No CAS ]

References: [1]Green Chemistry,2018,vol. 20,p. 1491 - 1498.

17
[ 34547-26-7 ]
[ 163266-02-2 ]
1-(5-hydroxy-3-(o-tolyl)-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-(2-methoxyphenyl)ethan-1-one [ No CAS ]