1322091-22-4|4-Fluoro-2-(p-tolylethynyl)benzaldehyde| Ambeed

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Quality Control of [ 1322091-22-4 ] Purity: 97% SDS Specification

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Product Details of [ 1322091-22-4 ]

CAS No. :	1322091-22-4
Formula :	C₁₆H₁₁FO
M.W :	238.26
SMILES Code :	O=CC1=CC=C(F)C=C1C#CC2=CC=C(C)C=C2
MDL No. :	MFCD28359715
InChI Key :	BDEXWXCUOIRBJP-UHFFFAOYSA-N
Pubchem ID :	121226438

Safety of [ 1322091-22-4 ]

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

Computational Chemistry of [ 1322091-22-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	12
Fraction Csp3	0.06
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	69.18
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.	2.94
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	3.87
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.85
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.	4.08
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	4.99
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.95

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.18
Solubility	0.0156 mg/ml ; 0.0000657 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.93
Solubility	0.0283 mg/ml ; 0.000119 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	-5.62
Solubility	0.000573 mg/ml ; 0.0000024 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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.	-5.01 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	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	2.0 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<2.0
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)	2.59

Application In Synthesis of [ 1322091-22-4 ]

* 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 [ 1322091-22-4 ]

[ 1322091-22-4 ] Synthesis Path-Downstream 1~24

1
[ 6914-71-2 ]
[ 1322091-22-4 ]
[ 1576-35-8 ]
[ 1338721-75-7 ]

References: [1]Synthesis,2011,p. 2268 - 2274.

2
[ 1322091-22-4 ]
[ 1576-35-8 ]
[ 538-75-0 ]
[ 1322091-31-5 ]

Yield	Reaction Conditions	Operation in experiment
32%	With silver trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 50 - 60℃;Inert atmosphere;	General procedure: Silver triflate (0.02 mmol, 10 mol %) was added to a solution of 2-alkynylbenzaldehyde 1 (0.2 mmol), sulfonohydrazide (0.2 mmol), and carbodiimide compound 2 (0.4 mmol, 2.0 equiv) in DCE (2.0 mL). The solution was stirred at 50-60 C for overnight. After completion of reaction as indicated by TLC, the reaction was quenched by addition of saturated aqueous NH4Cl (5.0 mL), and the mixture was extracted with EtOAc (4.0 mL×3). The combined organic layer was dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel to provide the desired product 3.

References: [1]Tetrahedron,2011,vol. 67,p. 5871 - 5877.

3
[ 1322091-22-4 ]
[ 1576-35-8 ]
[ 693-13-0 ]
[ 1322091-44-0 ]

Yield	Reaction Conditions	Operation in experiment
58%	With silver trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 50 - 60℃;Inert atmosphere;	General procedure: Silver triflate (0.02 mmol, 10 mol %) was added to a solution of 2-alkynylbenzaldehyde 1 (0.2 mmol), sulfonohydrazide (0.2 mmol), and carbodiimide compound 2 (0.4 mmol, 2.0 equiv) in DCE (2.0 mL). The solution was stirred at 50-60 C for overnight. After completion of reaction as indicated by TLC, the reaction was quenched by addition of saturated aqueous NH4Cl (5.0 mL), and the mixture was extracted with EtOAc (4.0 mL×3). The combined organic layer was dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel to provide the desired product 3.

References: [1]Tetrahedron,2011,vol. 67,p. 5871 - 5877.

4
[ 1322091-22-4 ]
[ 1383274-43-8 ]

References: [1]Tetrahedron,2012,vol. 68,p. 5197 - 5202.

5
[ 1322091-22-4 ]
[ 1576-35-8 ]
[ 1400575-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 0.5h;	General procedure: A mixture of 2-alkynylbenzaldehyde 1 (0.20 mmol) and 4-methylbenzenesulfonohydrazide (0.24 mmol, 1.2 equiv) in anhydrous dichloromethane (0.5 mL) was stirred at room temperature for half an hour. Then bromine (0.24 mmol, 1.2 equiv) and DABCO (0.24 mmol, 1.2 equiv) were added. After stirred at room temperature for 10 min, carbodiimide 2 (0.40 mmol, 2.0 equiv) in anhydrous acetonitrile (1.0 mL) was added. After completion of reaction as indicated by TLC, the reaction was quenched with a saturated NH4Cl solution (3.0 mL). The mixture was stirred for an additional 10 min and extracted with EtOAc (3.0 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuum. The crude residue was purified by flash column chromatography (EtOAc/n-hexane, 1:4) to give the desired 1-(4-bromoisoquinolin-1-yl)guanidine 3.

References: [1]Tetrahedron,2012,vol. 68,p. 5197 - 5202.

6
[ 1322091-22-4 ]
[ 1576-35-8 ]
C₂₃H₁₈BrFN₂O₂S [ No CAS ]

References: [1]Tetrahedron,2012,vol. 68,p. 5197 - 5202.

7
[ 1322091-22-4 ]
[ 54016-70-5 ]
1-ethyl-5-fluoro-2-methyl-3-(p-tolyl)indeno[2,1-b]pyrrol-8(1H)-one [ No CAS ]
3-hydroxypropanethioic O-acid [ No CAS ]

References: [1]Chemical Communications,2015,vol. 51,p. 13012 - 13015.

8
[ 1322091-22-4 ]
[ 2751-25-9 ]
3-((4-chlorophenyl)sulfonyl)-1-diazo-5-fluoro-2-(p-tolyl)-1H-indene [ No CAS ]

References: [1]Organic Letters,2016,vol. 18,p. 1884 - 1887.

9
[ 1322091-22-4 ]
6-fluoro-3-(p-tolyl)isoquinoline [ No CAS ]

References: [1]Chinese Journal of Chemistry,2016,vol. 34,p. 857 - 860.
[2]Synlett,2016,vol. 27,p. 2597 - 2600.

10
[ 1322091-22-4 ]
C₁₆H₁₃FN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrochloride; In ethanol; at 20℃; for 3.0h;	General procedure: To a solution of 2-(phenylethynyl)benzaldehyde 1a (62.0 mg, 0.3 mmol) in EtOH (5 mL) was added hydrazine monohydrochloride (30.6 mg, 0.45 mmol). The mixture was stirred at room temperature for 3h. Then the solid was filterred and used in the next step without further purification. The crude aromatic hydrazones 3a was disolved in DMSO (3 mL). Then AgNO3 (51.0 mg, 0.3 mmol) was added, the mixture was stirred at 100 C until all starting material has been consumed. Purification furnished the corresponding isoquinoline 2a

References: [1]Synlett,2016,vol. 27,p. 2597 - 2600.

11
[ 1322091-22-4 ]
[ 123-54-6 ]
3-(6-fluoro-3-(p-tolyl)-1H-isochromen-1-yl)pentane-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With diphenyl hydrogen phosphate; silver carbonate; In hexane; at 40℃; for 12.0h;	General procedure: A dry single-necked flask was charged with 2-alkynylaldehyde 1 (0.4 mmol, 1 equiv), ketone 2 (0.8 mmol, 2 equiv), and diphenylphosphate (10 mg, 0.04 mmol, 10 mol %) in hexane (2.4 mL), and silver carbonate (2.75 mg 0.01 mmol, 2.5 mol%) was added. The mixture was heated to 40 C and stirred until the 2-alkynylaldehyde was completely consumed (progress of the reaction was monitored by TLC). The hexane was evaporated and the mixture was diluted in EtOAc (50 mL) and washed three times with water. The organic layer was dried over anhydrous Na2SO4 and filtered. After evaporating the EtOAc, the crude product was dissolved in dichloromethane and purified by column chromatography (silica gel; pentane/EtOAc, 96:4) to give pure 1H-isochromenes 3 as yellow oils or as colorless solids. In the case of phenylacetone and 2-phenylcyclohexanone as ketone nucleophiles, the crude product was directly purified by flash chromatography on silica gel.