40261-59-4|1-Phenyl-1H-pyrazole-3-carbaldehyde| Ambeed

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Quality Control of [ 40261-59-4 ] Purity: 95% SDS Specification

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Product Details of [ 40261-59-4 ]

CAS No. :	40261-59-4
Formula :	C₁₀H₈N₂O
M.W :	172.18
SMILES Code :	O=CC1=NN(C2=CC=CC=C2)C=C1
MDL No. :	MFCD08437287
InChI Key :	FDKVVJDPHDRHQS-UHFFFAOYSA-N
Pubchem ID :	13432476

Safety of [ 40261-59-4 ]

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

Computational Chemistry of [ 40261-59-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	11
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	48.95
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	34.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.5
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	1.69
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.68
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.	1.07
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	1.67
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.52

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.47
Solubility	0.588 mg/ml ; 0.00342 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.	-2.04
Solubility	1.58 mg/ml ; 0.00917 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	-2.87
Solubility	0.232 mg/ml ; 0.00135 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.	-6.15 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	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)	1.43

Application In Synthesis of [ 40261-59-4 ]

* 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 [ 40261-59-4 ]

[ 40261-59-4 ] Synthesis Path-Downstream 1~23

1
[ 98700-39-1 ]
[ 508191-77-3 ]
[ 40261-59-4 ]
[ 98700-44-8 ]
[ 98700-43-7 ]

References: [1]Liebigs Annalen der Chemie,1985,p. 1377 - 1388.

2
[ 98700-38-0 ]
[ 508191-77-3 ]
[ 110-91-8 ]
[ 40261-59-4 ]
[ 98700-42-6 ]
[ 98700-40-4 ]

References: [1]Liebigs Annalen der Chemie,1985,p. 1377 - 1388.

3
[ 74073-15-7 ]
[ 508191-77-3 ]
[ 40261-59-4 ]

References: [1]Liebigs Annalen der Chemie,1985,p. 1377 - 1388.

4
[ 98700-42-6 ]
[ 40261-59-4 ]

References: [1]Liebigs Annalen der Chemie,1985,p. 1377 - 1388.

6
[ 98700-40-4 ]
[ 40261-59-4 ]

References: [1]Liebigs Annalen der Chemie,1985,p. 1377 - 1388.

7
[ 508191-77-3 ]
[ 40261-59-4 ]

References: [1]Liebigs Annalen der Chemie,1985,p. 1377 - 1388.

8
[ 7189-08-4 ]
[ 40261-59-4 ]

Yield	Reaction Conditions	Operation in experiment
45%	With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0℃; for 3h;	500 mg (2.9 mmol) of 2- (l-phenyl-lH-pyrrazole-3-yl)-methanol and 0.8 ml (5.7 mmol) of triethylamine were stirred in 10 ml of dichloromethane at 0C. 690 mg (4.3 mmol) of sulfur trioxide pyridine was dissolved in 5 ml of dimethylsulfoxide and the resulting solution was added to reaction solution. After 3 hours later, ethylacetate was added thereto, followed by washing with water. The organic solution thus obtained was dried over anhydrous magnesium sulfate, and the residue was purified by column chromatography to obtain 220 mg of the title compound in a yield of 45%. NMR : lH-NMR (CDCl3) 6 9.98 (1H, s), 8.44 (1H, s), 8.17 (1H, s), 7. 74-7. 71 (2H, m), 7. 53-7. 49 (2H, m), 7. 42-7. 38 (1H, m) Mass (EI) 173 (M++1)

References: [1]Patent: WO2005/40127,2005,A1 .Location in patent: Page/Page column 141.
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 6535 - 6538.

9
[ 4009-98-7 ]
[ 40261-59-4 ]
3-(2-methoxy-vinyl)-1-phenyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		660 mg (1.9 mmol) of methoxymethyl-triphenylphosphonium chloride was dissolved in 10 ml of tetrahydrofuran, then n-butyl lithium was added to the resulting at - 78C. After 30 minutes, the reaction was heated to 0C and 2 ml of hexamethylphosphoamide was added thereto, then 220 mg (1.3 mmol) of 1-phenyl-lH- pyrrazole-3-carbaldehyde dissolved in 3 ml of tetrahydrofuran was further added thereto. After stirring for 1 hour, ethylacetate was added, followed by washing with ammonium chloride solution. The organic solution thus obtained was dried over anhydrous ammonium sulfate, the residue was purified by column chromatography to obtain 3- (2- methoxy-vinyl)-1-phenyl-lH-pyrazole. This compound was dissolved in a mixture of 3 ml of 3 N hydrogen chloride solution and 20 ml of tetrahydrofuran, then the resulting solution was stirred with heating for 2 hours. Ethylacetate was added thereto and the resulting solution was washed with water, then the organic solution thus obtained was dried over anhydrous magnesium sulfate, and the residue was purified by column chromatography to obtain 130 mg of the title compound in a yield of 36%. Mass (EI) 187 (M++1)

References: [1]Patent: WO2005/40127,2005,A1 .Location in patent: Page/Page column 141-142.

10
[ 3886-69-9 ]
[ 40261-59-4 ]
[ 1195985-36-4 ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6535 - 6538.

11
[ 925-90-6 ]
[ 40261-59-4 ]
[ 1226694-03-6 ]

Yield	Reaction Conditions	Operation in experiment
69%	In tetrahydrofuran; diethyl ether; at 20℃;Cooling;	Step 1 : l-(l-Phenyl-lH-pyrazol-3-yl)-propan-l-ol[0142] 1 -Phenyl- lH-pyrazole-3-carbaldehyde (779 mg, 4.53 mmol) was dissolved in anhydrous TEtaF (9 mL) and chilled in an ice bath. EtMgBr (3.0 M in Et20, 4.5 mL) was added dropwise. After 1.5 hours, the reaction mixture was allowed to warm to ambient temperature. TLC (2:1 hexanes:EtOAc indicated complete consumption of aldehyde starting material. The reaction mixture was quenched with water and extracted with EtOAc (2x). The EtOAc layers were washed with brine (Ix), dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (2:1 hexanes: EtOAc) to provide the title compound (631 mg, 69%) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.85 (d, IH, J= 2.4 Hz), 7.65 (d, 2H, J= 7.6 Hz), 7.42 (t, 2H, J= 7.6 Hz), 7.27 (d, IH, J= 7.2 Hz), 6.38 (d, IH, J = 2.4 Hz), 4.79 (dd, IH, J= 12, 5.6 Hz), 2.38 (d, IH, J= 4.8 Hz), 1.98-1.81 (m, 2H), 1.01 (t, 3H, J= 7.2 Hz). MS (ES) m/z 203.1 (M+H+).

References: [1]Patent: WO2010/54006,2010,A1 .Location in patent: Page/Page column 47.

12
[ 1226694-56-9 ]
[ 40261-59-4 ]
[ 1226692-38-1 ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 3h;	Step 5: (6-Methyl-8-[4-(l-phenyl-lH-pyrazol-3-ylmethyl)- [l,4]diazepan-l-yl]-quinolin-7- yloxy} -acetic acid ethyl ester[0186] A mixture of (8-[ 1 ,4]diazepan- 1 -yl-6-methyl-quinolin-7-yloxy)-acetic acid ethyl ester (600 mg, 1.75 mmol), 1 -Phenyl- lH-pyrazole-3-carbaldehyde (300.8 mg, 1.75) and NaBH(OAc)3 (408 mg, 1.92 mmol) in DCE (5 ml) was stirred at rt for 3 hrs. The reaction was then diluted with DCE (20 ml), filtered, and purified by flash column chromatography on silica gel to give the desired product (500 mg, 57%). MS (ES) mlz 500.2 (M+ H+).

References: [1]Patent: WO2010/54006,2010,A1 .Location in patent: Page/Page column 72.

13
[ 50479-11-3 ]
[ 40261-59-4 ]
(Z)-ethyl 5-(1-phenyl-1H-pyrazol-3-yl)pent-4-enoate [ No CAS ]