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Quality Control of [ 139229-57-5 ] Purity: 97% SDS Specification

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Product Details of [ 139229-57-5 ]

CAS No. :	139229-57-5
Formula :	C₇H₉F₃O₂
M.W :	182.14
SMILES Code :	O=C(C1(C(F)(F)F)CC1)OCC
MDL No. :	MFCD22199506
InChI Key :	XKNRIQDQYMPZKZ-UHFFFAOYSA-N
Pubchem ID :	14996286

Safety of [ 139229-57-5 ]

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

Calculated chemistry of [ 139229-57-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	0
Fraction Csp3	0.86
Num. rotatable bonds	4
Num. H-bond acceptors	5.0
Num. H-bond donors	0.0
Molar Refractivity	34.87
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.17
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	1.87
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.09
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.	1.73
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	2.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.24

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.88
Solubility	2.38 mg/ml ; 0.0131 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.	-2.04
Solubility	1.65 mg/ml ; 0.00904 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	-2.07
Solubility	1.56 mg/ml ; 0.00859 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.	-6.08 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	1.0
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)	1.72

Application In Synthesis of [ 139229-57-5 ]

* 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 [ 139229-57-5 ]

[ 139229-57-5 ] Synthesis Path-Downstream 1~14

1
[ 3697-66-3 ]
1-fluorocarbonyl-cyclopropanecarboxylic acid ethyl ester [ No CAS ]
[ 139229-57-5 ]

References: [1]Journal of Fluorine Chemistry,2000,vol. 104,p. 297 - 301.

2
[ 1559-02-0 ]
[ 139229-57-5 ]

References: [1]Journal of Fluorine Chemistry,2000,vol. 104,p. 297 - 301.

3
methyl 2-(2-bromomethylphenyl)-3-methoxyacrylate [ No CAS ]
[ 139229-57-5 ]
Methyl alpha-{2-[1-(trifluoromethyl)-cyclopropylcarbonyloxymethyl]-phenyl}-beta-methoxyacrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium hydroxide; In N-methyl-acetamide; ethanol; water;	EXAMPLE 5 (Compound No. 7 in Table 1) Methyl alpha-{2-[1-(trifluoromethyl)-cyclopropylcarbonyloxymethyl]-phenyl}-beta-methoxyacrylate STR18 A solution of 10.0 g (55 mmol) of <strong>[139229-57-5]ethyl 1-trifluoromethylcyclopropanecarboxylate</strong> and 3.4 g (61 mmol) of potassium hydroxide in 150 ml of ethanol was stirred for 4 hours at 40 C. and then evaporated down. The residue was covered with a layer of diethyl ether, after which the resulting precipitate was separated off, washed with diethyl ether and suspended in 100 ml of dimethylformamide. 10.0 g (35 mmol) of methyl alpha-(2-bromo-methylphenyl)-beta-methoxyacrylate were added to this suspension and the mixture was then heated for 2 hours at 95 C. After cooling to 20 C., the mixture was hydrolyzed with 50 ml of water. The product was then extracted with diethyl ether and isolated in a conventional manner. The oily crude product was covered with a layer of pentane and was crystallized by rubbing the wall of the vessel. Yield: 64%; mp.: 58-60 C.; white crystals.

References: [1]Patent: US5371268,1994,A .

4
sulfur tetrafluoride [ No CAS ]
[ 3697-66-3 ]
[ 7440-47-3 ]
[ 7440-02-0 ]
[ 7439-98-7 ]
[ 139229-57-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With hydrogen fluoride; In dichloromethane;	Ethyl 1-trifluoromethylcyclopropanecarboxylate STR20 31.6 g (0.20 mol) of monoethyl cyclopropane-1,1-dicarboxylate, 126 g (1.16 mol) of sulfur tetrafluoride, 100 ml of dichloromethane and 1.5 g (75 mmol) of hydrogen fluoride were introduced at -70 C. into a 500 ml stirred autoclave which was lined with an alloy of 70% of nickel, 15% of chromium and 15% of molybdenum. The mixture was heated for 48 hours at 80 C. and the gaseous constituents were destroyed, after cooling the autoclave to 35 C., by passing them into a wash tower filled with potassium hydroxide. The residue was dissolved in 100 ml of dichloromethane. The solution was washed with 100 ml of saturated sodium bicarbonate solution, after which the organic phase was dried with sodium sulfate and potassium fluoride and was separated into the individual components by distillation. Yield: 76%; bp.: 141-142 C.; oil.

References: [1]Patent: US5371268,1994,A .

5
[ 139229-57-5 ]
[ 1188920-79-7 ]