802919-90-0|((Difluoroiodomethyl)sulfonyl)benzene| Ambeed

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Quality Control of [ 802919-90-0 ] Purity: 98% SDS Specification

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Product Details of [ 802919-90-0 ]

CAS No. :	802919-90-0
Formula :	C₇H₅F₂IO₂S
M.W :	318.08
SMILES Code :	O=S(C1=CC=CC=C1)(C(F)(F)I)=O
MDL No. :	MFCD28100936
InChI Key :	LIPDDCLPIKKOTB-UHFFFAOYSA-N
Pubchem ID :	12158450

Safety of [ 802919-90-0 ]

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

Computational Chemistry of [ 802919-90-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	52.64
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	42.52 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.68
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	3.0
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.37
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.	2.47
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	2.25
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.75

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.91
Solubility	0.039 mg/ml ; 0.000123 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.	-3.56
Solubility	0.0882 mg/ml ; 0.000277 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	-3.86
Solubility	0.0439 mg/ml ; 0.000138 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.	-6.11 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.	0.55

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<0.0
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)	2.46

Application In Synthesis of [ 802919-90-0 ]

* 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.

Downstream synthetic route of [ 802919-90-0 ]

[ 802919-90-0 ] Synthesis Path-Downstream 1~35

1
[ 1535-65-5 ]
[ 802919-90-0 ]

Yield	Reaction Conditions	Operation in experiment
92%		Under an argon atmosphere, into a Schlenk flask containing difluoromethyl phenyl sulfone (192 mg, 1 mmol) and elemental iodine (508 mg, 4 mmol) in DMF (4 mL) at - 30 C, was added dropwise via a syringe t-BuOK (448 mg, 4 mmol) in DMF (4 mL). The reaction mixture was stirred at - 30 - - 20 C for 1 h, and the completion of the reaction was monitored by 19F NMR. The reaction was then quenched by adding IN HCI aqueous solution (5 mL) at - 50 C, followed by warming to room temperature. A saturated NaCl aqueous solution (10 mL) was added, and the mixture was extracted with Et20 (15 mL x 3). The combined organic phase was dried over MgS04, filtered, and the solvent was removed in a rotary evaporator. The residue was further purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1) to give difluoroiodomethyl phenyl sulfone (5) (294 mg, 92 % yield) as a colorless solid, which readily turns to red under light. 'H NMR (500 MHz, CDC13): 6 7.63 (t, J = 7.4 Hz, 2H) ; 7.79 (t, J = 7.4 Hz, 1H) ; 7.99 (d, J = 7.5 Hz, 2H). ¹3C NMR (125 MHz, CDC13): 6 102.5 (t, J = 355 Hz) ; 128.1; 129.7; 131.3; 136.1.19F NMR (470 MHz, CDC13): 6 - 52.2. MS (EI, m/z): 318 (M(at); 177; 142; 127. HRMS (El): m/z calcd for C7H5F2IO2S (M+) 317.9023, found 317.9013.
92%	With iodine(I) bromide; potassium hydroxide; In tetrachloromethane; at 20 - 60℃; for 4h;	General procedure: To a solution of proper sulfone1 (10.0 mmol) in dry CCl4 (40 mL) powdered KOH (2.0 g,35.7 mmol) was added. The mixture was stirred and IBr (2.2 g, 10.6 mmol) in dry CCl4 (30mL) was added dropwise while maintaining the temperature of the mixture below 20 C. Theresulting mixture was stirred for 2 h at room temperature, then for 2 h at 60 C. After coolingto room temperature the precipitate of inorganic salts was filtered off and the filtrate wasevaporated to dryness under reduced pressure. The residue was crystallized from propan-2-ol.For the synthesis of the sulfone 5 amount of IBr and KOH was increased twice.

References: [1]Organic Letters,2004,vol. 6,p. 4315 - 4317.
[2]Patent: WO2005/97739,2005,A2 .Location in patent: Page/Page column 9; 17.
[3]Tetrahedron Letters,2014,vol. 55,p. 745 - 748.
[4]Patent: WO2005/97739,2005,A2 .Location in patent: Page/Page column 9.

2
[ 935426-17-8 ]
[ 802919-90-0 ]

References: [1]Mendeleev Communications,2006,vol. 16,p. 132 - 134.

3
[ 54653-25-7 ]
[ 802919-90-0 ]
[ 946485-28-5 ]