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Quality Control of [ 6223-83-2 ] Purity: 97% SDS Specification

COA

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NMR

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Product Details of [ 6223-83-2 ]

CAS No. :	6223-83-2
Formula :	C₁₄H₈O₃
M.W :	224.21
SMILES Code :	OC(=O)C1=C2C(=CC=C1)C(=O)C1=CC=CC=C21
MDL No. :	MFCD00001145
InChI Key :	AFQYQSWTVCNJQT-UHFFFAOYSA-N
Pubchem ID :	80361

Safety of [ 6223-83-2 ]

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

Computational Chemistry of [ 6223-83-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	62.27
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.37 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.53
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	2.59
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.6
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.	2.06
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	3.01
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.36

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.32
Solubility	0.108 mg/ml ; 0.000481 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.	-3.38
Solubility	0.0933 mg/ml ; 0.000416 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	-4.46
Solubility	0.00785 mg/ml ; 0.000035 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	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.	-5.83 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.	0.56

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)	2.23

Application In Synthesis of [ 6223-83-2 ]

* 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 [ 6223-83-2 ]

[ 6223-83-2 ] Synthesis Path-Downstream 1~30

1
[ 6050-13-1 ]
[ 5435-44-9 ]
[ 6223-83-2 ]

References: [1]Journal of the American Chemical Society,1923,vol. 45,p. 3074.

2
[ 6050-13-1 ]
[ 71-43-2 ]
[ 214851-72-6 ]
[ 6223-83-2 ]

References: [1]Monatshefte fur Chemie,1902,vol. 23,p. 29.

3
[ 6050-13-1 ]
[ 6223-83-2 ]

References: [1]Journal of the American Chemical Society,1923,vol. 45,p. 3074.
[2]Monatshefte fur Chemie,1902,vol. 23,p. 29.
[3]Monatshefte fur Chemie,1904,vol. 25,p. 980.
[4]Journal of the American Chemical Society,1923,vol. 45,p. 3074.
[5]Journal of the Chemical Society,1938,p. 1561,1564.
[6]Journal of the Chemical Society,1938,p. 1561,1564.

4
[ 3240-34-4 ]
[ 6223-83-2 ]
[ 57357-29-6 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1975,vol. 11,p. 1246 - 1249.
Zhurnal Organicheskoi Khimii,1975,vol. 11,p. 1259 - 1262.

5
[ 92548-76-0 ]
[ 6223-83-2 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1963,vol. 22,p. 47 - 58.

6
[ 6223-83-2 ]
[ 42523-41-1 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 8359 - 8362.

7
[ 110-89-4 ]
n-butyl 9-fluorenone-4-carboxylate ester [ No CAS ]
[ 6223-83-2 ]
[ 109-77-3 ]
[ 71-36-3 ]
[ 93376-18-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; sodium hydrogencarbonate; In methanol; water; acetone; toluene;	Preparation Example 5 Preparation of Compound (26) The following is a description of the preparation of a dicyanofluorene-based compound Compound (26) to be used as an ETM in Comparative Example 1. A mixture of 70 g (0.312 mole) of <strong>[6223-83-2]9-fluorenone-4-carboxylic acid</strong> (from Sigma-Aldrich, Milwaukee, Wis.), 480 g (6.5 mole) of n-butanol (manufactured from Fisher Scientific Company Inc., Hanover Park, Ill.), 1000 ml of toluene, and 4 ml of concentrated sulfuric acid were added to a 2-liter round bottom flask equipped with a mechanical stirrer and a reflux condenser with a Dean Stark apparatus. With aggressive agitation, the solution was refluxed for 5 hours, during which time about 6 g of water was collected in the Dean Stark apparatus. After refluxing, the flask was cooled to room temperature. The solvents were evaporated and the residue was added with agitation to 4-liter of a 3% aqueous solution of sodium bicarbonate. The solid was filtered off, washed with water until the pH of the washed water was neutral, and dried under a hood overnight. The product was n-butyl 9-fluorenone-4-carboxylate ester. The yield was 70 g (80%). A mixture of 70 g (0.25 mole) of n-butyl 9-fluorenone-4-carboxylate ester, 750 ml of absolute methanol, 37 g (0.55 mole) of malononitrile (from Sigma-Aldrich, Milwaukee, Wis.), 20 drops of piperidine (from Sigma-Aldrich, Milwaukee, Wis.) was added to a 2-liter, 3-neck round bottom flask equipped with a mechanical stirrer and a reflux condenser. The solution was refluxed for 8 hours and the flask was cooled to room temperature. The orange crude product was filtered, washed twice with 70 ml of methanol and once with 150 ml of water, and dried overnight in a hood. This orange crude product was recrystallized from a mixture of 600 ml of acetone and 300 ml of methanol using activated charcoal. The flask was placed at 0 C. for 16 hours. The crystals formed were filtered and dried in a vacuum oven at 50 C. for 6 hours to obtain 60 g of pure (4-n-butoxycarbonyl-9-fluorenylidene)malononitrile (Compound (26)).

References: [1]Patent: US2006/183044,2006,A1 .

8
[ 6223-83-2 ]
5-chloro-2-[(9-oxo-9<i>H</i>-fluorene-4-carbonyl)-amino]-benzoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7960 - 7969.

9
[ 6223-83-2 ]
[ 295801-31-9 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 5355 - 5359.

10
[ 6223-83-2 ]
N-(2-(β-cyanoethyl-N,N'-diisopropylphosphino)ethyl)-9-fluorenone-4-carboxamide [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 5355 - 5359.

11
[ 6223-83-2 ]
[ 99585-29-2 ]

References: [1]Mutation Research - Genetic Toxicology,1996,vol. 369,p. 147 - 155.
[2]Journal of Organic Chemistry,1955,vol. 20,p. 1396,1399.

12
[ 6223-83-2 ]
[ 7256-04-4 ]

References: [1]Mutation Research - Genetic Toxicology,1996,vol. 369,p. 147 - 155.
[2]Journal of Organic Chemistry,1955,vol. 20,p. 1396,1399.

13
[ 6223-83-2 ]
[ 116668-29-2 ]

References: [1]Mutation Research - Genetic Toxicology,1996,vol. 369,p. 147 - 155.
[2]Journal of Organic Chemistry,1955,vol. 20,p. 1396,1399.

14
[ 6223-83-2 ]
[ 4269-20-9 ]