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Chemical Structure| 5906-98-9 Chemical Structure| 5906-98-9

Structure of 5906-98-9

Chemical Structure| 5906-98-9

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Product Details of [ 5906-98-9 ]

CAS No. :5906-98-9
Formula : C6H7ClN2O2S
M.W : 206.65
SMILES Code : O=S(C1=CC=CC=C1Cl)(NN)=O
MDL No. :MFCD08457460
InChI Key :JXYCJRIKOCVGAF-UHFFFAOYSA-N
Pubchem ID :20277438

Safety of [ 5906-98-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H319-H228
Precautionary Statements:P240-P210-P241-P264-P280-P370+P378-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362
Class:4.1
UN#:1325
Packing Group:

Computational Chemistry of [ 5906-98-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 45.25
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

80.57 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.94
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.39
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.57
Log Po/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.

0.86
Log Po/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

-0.12
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.73

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.6
Solubility 5.13 mg/ml ; 0.0248 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.65
Solubility 4.65 mg/ml ; 0.0225 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very 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

-2.64
Solubility 0.477 mg/ml ; 0.00231 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

No
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

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.

-7.28 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

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)

2.02

Application In Synthesis of [ 5906-98-9 ]

* 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 [ 5906-98-9 ]

[ 5906-98-9 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 5906-98-9 ]
  • 1-(5,7-dimethyl-[1,2,4]triazolo[1,5-<i>a</i>]pyrimidin-2-ylsulfanyl)-propan-2-one [ No CAS ]
  • C16H17ClN6O2S2 [ No CAS ]
  • 2
  • [ 5906-98-9 ]
  • 1-(5,7-dimethyl-[1,2,4]triazolo[1,5-<i>a</i>]pyrimidin-2-ylsulfanyl)-butane-2,3-dione [ No CAS ]
  • C23H22Cl2N8O4S3 [ No CAS ]
  • 3
  • [ 5906-98-9 ]
  • [ 262859-22-3 ]
  • N-[2-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-ylthio)cyclohexylidenamino]-2-chlorobenzenesulfonamide [ No CAS ]
  • 4
  • [ 5906-98-9 ]
  • [ 170301-01-6 ]
  • 2-chloro-<i>N</i>-(6-fluoro-4-oxo-2-phenyl-4<i>H</i>-quinazolin-3-yl)-benzenesulfonamide [ No CAS ]
  • C20H15ClFN3O4S [ No CAS ]
  • 5
  • [ 5906-98-9 ]
  • 2-benzyl-6-fluoro-benzo[<i>d</i>][1,3]oxazin-4-one [ No CAS ]
  • <i>N</i>-(2-benzyl-6-fluoro-4-oxo-4<i>H</i>-quinazolin-3-yl)-2-chloro-benzenesulfonamide [ No CAS ]
  • C21H17ClFN3O4S [ No CAS ]
  • 6
  • [ 5906-98-9 ]
  • 6-fluoro-2-thiophen-2-ylmethyl-benzo[<i>d</i>][1,3]oxazin-4-one [ No CAS ]
  • 2-chloro-<i>N</i>-(6-fluoro-4-oxo-2-thiophen-2-ylmethyl-4<i>H</i>-quinazolin-3-yl)-benzenesulfonamide [ No CAS ]
  • C19H15ClFN3O4S2 [ No CAS ]
  • 7
  • [ 5906-98-9 ]
  • 6-fluoro-2-phenethyl-benzo[<i>d</i>][1,3]oxazin-4-one [ No CAS ]
  • 2-chloro-<i>N</i>-(6-fluoro-4-oxo-2-phenethyl-4<i>H</i>-quinazolin-3-yl)-benzenesulfonamide [ No CAS ]
  • C22H19ClFN3O4S [ No CAS ]
  • 8
  • N-methyl-N'-benzenesulfonyl-2-methylacrylamide [ No CAS ]
  • [ 5906-98-9 ]
  • [ 1620220-70-3 ]
  • 9
  • [ 110-82-7 ]
  • [ 5906-98-9 ]
  • [ 1610363-64-8 ]
  • 10
  • [ 292-64-8 ]
  • [ 5906-98-9 ]
  • [ 1616956-05-8 ]
  • 11
  • [ 287-92-3 ]
  • [ 5906-98-9 ]
  • [ 1003015-19-7 ]
  • 12
  • [ 109-99-9 ]
  • [ 5906-98-9 ]
  • [ 1616956-11-6 ]
  • 13
  • [ 57957-24-1 ]
  • [ 5906-98-9 ]
  • [ 222639-42-1 ]
  • 14
  • [ 1522-13-0 ]
  • [ 5906-98-9 ]
  • (3-((2-chlorophenyl)sulfonyl)propa-1,2-diene-1,1,3-triyl)tribenzene [ No CAS ]
  • 15
  • [ 5906-98-9 ]
  • C21H13ClF2O [ No CAS ]
  • 4,4'-(3-(4-chlorophenyl)-3-((2-chlorophenyl)sulfonyl)propa-1,2-diene-1,1-diyl)bis(fluorobenzene) [ No CAS ]
  • 16
  • [ 2206-94-2 ]
  • [ 5906-98-9 ]
  • [ 222639-42-1 ]
YieldReaction ConditionsOperation in experiment
54% With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In water; acetonitrile; at 80.0℃; for 8.0h; General procedure: To a stirred solution of vinyl acetate (0.3 mmol), TsNHNH2 (0.54 mmol) and TBAI (0.06 mmol) in MeCN (2 mL) was added TBHP (0.6 mmol, 70% aqueous solution) at room temperature. The mixture was heated at 80 oC for 8 h and cooled down to room temperature. The excess solvent was removed under vacuum, and the residue was purified by silica gel column chromatography to afford desired beta-keto-sulfones .
  • 17
  • [ 5906-98-9 ]
  • C26H23NO3S [ No CAS ]
  • 11-chloro-2,6a-dimethyl-5-(phenylsulfonyl)-12-(p-tolyl)-6a,7-dihydrobenzo[j]phenanthridin-6(5H)-one [ No CAS ]
  • C32H26ClNO3S [ No CAS ]
  • 18
  • [ 5906-98-9 ]
  • [ 121-69-7 ]
  • 4-((2-chlorophenyl)thio)-N,N-dimethylaniline [ No CAS ]
  • 19
  • [ 5906-98-9 ]
  • [ 98-95-3 ]
  • 2-chloro-N-phenylbenzenesulfonamide [ No CAS ]
  • 20
  • [ 5906-98-9 ]
  • N-[2-(phenylethynyl)-phenyl]-N-tosylmethacrylamide [ No CAS ]
  • 3-(((2-chlorophenyl)sulfonyl)methyl)-4-(iodo(phenyl)methylene)-3-methyl-1-tosyl-3,4-dihydroquinolin-2(1H)-one [ No CAS ]
  • 21
  • [ 67-56-1 ]
  • [ 5906-98-9 ]
  • 2-chlorobenzenesulfinic acid methyl ester [ No CAS ]
  • 23
  • [ 1180487-37-9 ]
  • [ 5906-98-9 ]
  • C25H15ClN2O2S [ No CAS ]
  • 24
  • [ 5906-98-9 ]
  • [ 135-19-3 ]
  • 1-((2-chlorophenyl)thio)naphthalen-2-ol [ No CAS ]
  • 25
  • [ 5906-98-9 ]
  • [ 91-59-8 ]
  • 1-((2-chlorophenyl)thio)naphthalen-2-amine [ No CAS ]
  • 26
  • [ 17572-78-0 ]
  • [ 5906-98-9 ]
  • 3-((2-chlorophenyl)thio)-2,5-diphenylfuran [ No CAS ]
  • 27
  • [ 5906-98-9 ]
  • [ 108-98-5 ]
  • [ 95173-82-3 ]
  • 28
  • [ 140-10-3 ]
  • [ 5906-98-9 ]
  • (E)-1-chloro-2-(styrylsulfonyl)benzene [ No CAS ]
  • 29
  • [ 292638-84-7 ]
  • [ 5906-98-9 ]
  • 2-((2-chlorophenyl)sulfonyl)-1-phenylethan-1-one oxime [ No CAS ]
  • 30
  • [ 5906-98-9 ]
  • [ 100-47-0 ]
  • [ 5162-03-8 ]
  • 31
  • [ 5906-98-9 ]
  • [ 2905-16-0 ]
YieldReaction ConditionsOperation in experiment
87% With dipotassium peroxodisulfate; N-iodo-succinimide; In tetrahydrofuran; at 70.0℃; for 8.0h;Schlenk technique; Green chemistry; General procedure: To a Schlenk tube were added sulfonyl hydrazides (0.3 mmol),NIS (0.06 mmol), K2S2O8 (0.36 mmol), and THF (2 mL). Then thetube was stirred open in air at 70 C for the indicated time untilcomplete consumption of starting material as monitored by TLCanalysis. After the reaction was finished, the solution was concentratedunder reduced pressure, and the mixture was purifiedby flash column chromatography over silica gel (hexane/ethylacetate) to afford the desired product 2 and was analyzed by 1HNMR and 13C NMR spectroscopy (see Supporting Information).
72% With dipotassium peroxodisulfate; tetrabutylammomium bromide; In water; at 40.0℃; under 760.051 Torr; for 24.0h;Schlenk technique; The sulfonyl hydrazide (41.2 mg, 0.2 mmol) of formula 1f was added to the Schlenk bottle.Tetrabutylammonium iodide (TBAI, 14.8 mg, 0.04 mmol),Potassium persulfate (K2S2O8, 64.8mg, 0.24mmol),Add solvent water (2mL),Then the reactor is in an air atmosphere,Stir the reaction at 40 C,The progress of the reaction was monitored by TLC until the disappearance of the starting material (reaction time was 24 hours).After the reaction is completed,The reaction solution was extracted three times with ethyl acetate.The organic phase is dried over anhydrous sodium sulfate.Filter and concentrate under reduced pressure to remove the solvent.The residue was subjected to column chromatography (yield solvent: ethyl acetate / n-hexane) to afford objective product I-6.(72% yield);
  • 32
  • [ 1076-38-6 ]
  • [ 5906-98-9 ]
  • 3-((2-chlorophenyl)thio)-4-hydroxy-2H-chromen-2-one [ No CAS ]
  • 33
  • [ 5906-98-9 ]
  • [ 536-74-3 ]
  • (E)-1chloro-2-((2-iodo-2-phenylvinyl)sulfonyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With iodine pentoxide; In 1,4-dioxane; at 80.0℃; for 7.0h;Sealed tube; Add phenylacetylene (51 mg, 0.5 mmol), <strong>[5906-98-9]2-chlorobenzenesulfonyl hydrazide</strong> (207 mg, 1.0 mmol), diiod pentoxide (167 mg, 0.5 mmol) and solvent 1,4-dioxane 2 mL to 10 mL sealed tube Medium, placed in an oil bath at 80 C and stirred for 7 h, the reaction After the completion of the heating, the heating was stopped, the sealed tube was cooled to room temperature, and the crude product was separated by column chromatography (eluent was a mixture of petroleum ether/ethyl acetate: 15:1) to give the product (E)-1-chloro- 2-((2-Iodo-2-styryl)sulfonyl)benzene (Compound 18) 139.55 mg (yield 69%).
  • 34
  • [ 2297-64-5 ]
  • [ 5906-98-9 ]
  • (E)-1-chloro-2-(styrylsulfonyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With dipotassium peroxodisulfate; tetra-(n-butyl)ammonium iodide; at 20.0℃; for 8.0h; (2) Step two:The above beta-nitrostyrene (74.5 mg, 0.5 mmol),O-chlorobenzenesulfonyl hydrazide (206 mg, 1.0 mmol),Tetrabutylammonium iodide (36.5 mg, 0.1 mmol) and potassium persulfate (270.0 mg, 1.0 mmol) were added to the flask.The mixture was reacted at 20 C for 8 hours.After TLC detects the reaction,Separated by column chromatography (eluent: petroleum ether / ethyl acetate volume ratio 9:1)1-phenyl 2-chlorobenzenesulfonyl olefin(Compound 10) 58.4 mg,The yield was 42%.
  • 35
  • [ 5906-98-9 ]
  • [ 536-74-3 ]
  • 2-((2-chlorophenyl)sulfonyl)-1-phenylethan-1-one oxime [ No CAS ]
 

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