90176-80-0|4-Fluoro-2-(trifluoromethyl)benzaldehyde| Ambeed

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Structure of 90176-80-0

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Quality Control of [ 90176-80-0 ] Purity: 95% SDS Specification

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Product Details of [ 90176-80-0 ]

CAS No. :	90176-80-0
Formula :	C₈H₄F₄O
M.W :	192.11
SMILES Code :	O=CC1=CC=C(F)C=C1C(F)(F)F
MDL No. :	MFCD00061313
Boiling Point :	No data available
InChI Key :	NONOHEMDNFTKCZ-UHFFFAOYSA-N
Pubchem ID :	522940

Safety of [ 90176-80-0 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H225-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338
Class:	3
UN#:	1989
Packing Group:	Ⅲ

Computational Chemistry of [ 90176-80-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	5.0
Num. H-bond donors	0.0
Molar Refractivity	36.79
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.73
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	2.37
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.23
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.	2.94
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	3.43
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.94

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.73
Solubility	0.355 mg/ml ; 0.00185 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.	-2.37
Solubility	0.821 mg/ml ; 0.00428 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	-3.51
Solubility	0.0588 mg/ml ; 0.000306 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	Yes
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.	-5.79 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	2.0
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)	1.5

Application In Synthesis of [ 90176-80-0 ]

* 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.

Upstream synthesis route of [ 90176-80-0 ]
Downstream synthetic route of [ 90176-80-0 ]

[ 90176-80-0 ] Synthesis Path-Upstream 1~1

1
[ 20277-69-4 ]
[ 90176-80-0 ]
[ 1215310-75-0 ]

References: [1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 582 - 586.
[2] Drugs of the Future, 2018, vol. 43, # 8, p. 565 - 572.

[ 90176-80-0 ] Synthesis Path-Downstream 1~35

1
[ 7677-24-9 ]
[ 90176-80-0 ]
(4-Fluoro-2-trifluoromethyl-phenyl)-trimethylsilanyloxy-acetonitrile [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 770 - 778.

2
[ 179556-97-9 ]
[ 90176-80-0 ]
[ 710971-52-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; In DMF (N,N-dimethyl-formamide); 1,2-dichloro-ethane; at 20℃; for 16h;	To a solution of 4-isobutylamino-piperidine-1-carboxylic acid tert-butyl ester (10 g, 39mmol, 1.0 eq) in 1,2-dichloroethane (100 ml) was added 2- (trifluoromethyl)-4- fluorobenzaldehyde (22. 5G, 117mmol, 3.0 eq). To this was added a solution of sodium triacetoxyborohydride (24.8g, 117mmol, 3.0 eq) in dimethylformamide (20 ml). This mixture was left to stir under nitrogen, at room temperature, for 16 h. After this time the reaction mixture was quenched with water (50 ml) and subsequently stirred vigorously for several minutes. The reaction mixture was then separated with DCM, washing the organic layer with water (x3). The combined organics were dried over sodium sulfate and evaporated in vacuo to give an oil. Purification of this crude oil by chromatography on silica was then performed using an Isco system, eluting with 0-50% ethyl acetate: Hexane gradient conditions over 40 mins gave product which was taken directly onto the next step.

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2714 - 2718.
[2]Patent: WO2004/52858,2004,A2 .Location in patent: Page 93.

3
[ 701298-37-5 ]
[ 90176-80-0 ]
[ 710978-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; In DMF (N,N-dimethyl-formamide); 1,2-dichloro-ethane; at 20℃; for 16h;	To a solution of amine prepared in intial step (2. 0g, 8. 19MMOL, L. Oeq) in dichloroethane (20 ml) was added the 4-fluoro, 2- (trifluoromethyl) benzaldehyde (2.34g, 12.2mmol, 1. 5eq). To this was added sodium triacetoxyborohydride (2.58g, 12. 2MMOL, 1. 5eq.) in DMF (lml). This mixture was left to stir under nitrogen, at room temperature for 16h. The reaction was worked up by addition of water (10 ml). The mixture was stirred vigorously for several minutes. The chlorinated organic layer was then run through a hydrophobic frit to remove water. The resulting organic solution was diluted with methanol (10 ml) and loaded onto an SCX-2 (lOg) column. The column was washed with methanol (50 ml) then basic material eluted with 2N ammonia in methanol. The ammonia/methanol solution was concentrated in vacuo to give an oil. This was further purified using ISCO chromatography, eluting with 0-40% ethyl acetate: iso-hexane ramp over 40 min to give the desired compound (0. 173G), which was taken onto the next step. To a solution of this oil (L. Oeq) in dichloromethane (10 ML) was added trifluoroacetic acid (TFA) (15EQ). The solution was stirred at room temperature for 4h. Solvent and TFA were removed in vacuo. The resulting oil was taken up in methanol and loaded onto an SCX-2 (10 g) column. The column was washed with methanol (50 ml). Basic material was then eluted using 2N ammonia in methanol (50 ml). Removal of solvent from the ammonia/methanol mixture under vacuum, gave the desired compound as an oil. The oil was taken up in diethyl ether. To this solution was added a solution OF FUMARIC acid (LEQ) in hot methanol and then cooled. The resulting precipitate was collected by filtration to give the title compound as a white solid (0.43g) ; IHNMR (MEOD) 6= 8.10- 8.0 (1H, m), 7.45-7. 33 (2H, m), 6.69 (2H, s), 3.91 (2H, s), 3.59-3. 41 (4H, m), 3.30-3. 21 (1H, s), 3.10-2. 81 (3H, m), 2.75-2. 68 (2H, m), 2.15 (2H, brd), 1.87-1. 70 (2H, m).

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2714 - 2718.
[2]Patent: WO2004/52858,2004,A2 .Location in patent: Page 151-152.

4
[ 710982-35-7 ]
[ 90176-80-0 ]
[ 888227-73-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2714 - 2718.

5
4-(3-cyano-propylamino)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
[ 90176-80-0 ]
[ 710982-52-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2714 - 2718.

6
[ 90176-80-0 ]
(E)-3-[4-(2-Methoxy-phenylsulfanyl)-2-trifluoromethyl-phenyl]-acryloyl chloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 4393 - 4403.

7
[ 90176-80-0 ]
[ 1027068-12-7 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 4393 - 4403.

8
[ 90176-80-0 ]
1-{(E)-3-[4-(2-Methoxy-phenylsulfanyl)-2-trifluoromethyl-phenyl]-acryloyl}-piperidine-4-carboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 4393 - 4403.

9
[ 90176-80-0 ]
1-{(E)-3-[4-(2-Methoxy-phenylsulfanyl)-2-trifluoromethyl-phenyl]-acryloyl}-piperidine-4-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 4393 - 4403.

10
[ 90176-80-0 ]
[ 1026628-86-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 694 - 707.

11
[ 90176-80-0 ]
[ 1026978-07-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 694 - 707.

12
[ 90176-80-0 ]
(2R,3R)-2-(2,4-Difluoro-phenyl)-3-{2-[(E)-2-(4-fluoro-2-trifluoromethyl-phenyl)-vinyl]-[1,3]dioxan-5-ylsulfanyl}-1-[1,2,4]triazol-1-yl-butan-2-ol [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 694 - 707.

13
[ 90176-80-0 ]
[ 220259-81-4 ]