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Chemical Structure| 38695-60-2 Chemical Structure| 38695-60-2

Structure of 38695-60-2

Chemical Structure| 38695-60-2

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Product Details of [ 38695-60-2 ]

CAS No. :38695-60-2
Formula : C5H6O2S2
M.W : 162.23
SMILES Code : O=S(C1=CC=CS1)(C)=O
MDL No. :MFCD00052826

Safety of [ 38695-60-2 ]

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

Computational Chemistry of [ 38695-60-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 5
Fraction Csp3 0.2
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 37.41
TPSA ?

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

70.76 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.34
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

0.38
Log Po/w (WLOGP)?

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

2.23
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.

0.43
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

1.84
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.25

Water Solubility

Log S (ESOL):?

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

-1.43
Solubility 6.02 mg/ml ; 0.0371 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.

-1.43
Solubility 6.01 mg/ml ; 0.037 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

-1.97
Solubility 1.75 mg/ml ; 0.0108 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

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.

-7.02 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

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)

2.54

Application In Synthesis of [ 38695-60-2 ]

* 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 [ 38695-60-2 ]

[ 38695-60-2 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 5780-36-9 ]
  • [ 38695-60-2 ]
YieldReaction ConditionsOperation in experiment
40% With 7H-benz<c>thioxanthen-7-one; oxygen; In acetonitrile; at 20℃;Sealed tube; Irradiation; General procedure: A solution of sulfides 1 (0.2 mmol, 1.0 equiv) or sulfoxides 2 (0.2 mmol, 1.0 equiv), photocatalyst (c, 5 mol%), and ACN (1 mL, 0.2 M) was sealed in an oven-dried reaction tube equipped with an oxygen balloon (gas-switch three times with oxygen balloon). The reaction was agitated under 18 W 405 nm LEDs at room temperature for 12 to 24 h. The progress of the reaction was monitored by GC-MS or/and TLC. After completion of the reaction, the solvent was removed under reduced pressure, and the crude product 3 was purified by flash silica chromatography using n-hexane and ethyl acetate as eluent (v/v, 80:20).
  • 2
  • [ 38695-60-2 ]
  • [ 107-30-2 ]
  • 5-methanesulfonyl-2,3-bis-phthalimidomethyl-thiophene [ No CAS ]
  • 3
  • [ 5780-36-9 ]
  • [ 38695-60-2 ]
  • [ 74166-42-0 ]
  • 4
  • [ 38695-60-2 ]
  • [ 6339-87-3 ]
  • 6
  • [ 74-88-4 ]
  • potassium thiophene-2-sulfinate [ No CAS ]
  • [ 38695-60-2 ]
  • 8
  • [ 188290-36-0 ]
  • [ 37073-15-7 ]
  • [ 38695-60-2 ]
  • 9
  • [ 1003-09-4 ]
  • [ 20277-69-4 ]
  • [ 38695-60-2 ]
  • 10
  • [ 38695-60-2 ]
  • [ 623-00-7 ]
  • [ 1313758-51-8 ]
  • 11
  • [ 38695-60-2 ]
  • [ 2042-37-7 ]
  • [ 1313758-54-1 ]
  • 12
  • [ 38695-60-2 ]
  • [ 99-90-1 ]
  • [ 1313758-52-9 ]
  • 13
  • [ 38695-60-2 ]
  • [ 1122-91-4 ]
  • [ 1313758-53-0 ]
  • 14
  • [ 20277-69-4 ]
  • [ 1026668-29-0 ]
  • [ 38695-60-2 ]
  • 15
  • [ 38695-60-2 ]
  • [ 59473-45-9 ]
  • 2-(2-iodophenyl)ethyl thienylsulfone [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% A solution of methyl thienyl sulfone (1.00 g, 6.16 mmol) in THF (14 mL) was added dropwise to a stirred suspension of NaH (0.2 g of a 80% dispersion in oil, 6.8 mmol) inTHF (1 mL) at room temperature. After 30 min, a solution of 2-iodobenzyl chloride (1.56 g, 6.16 mmol) in THF (15 mL) was added and the resulting mixture stirred for 48 h. The reaction mixture was heated at reflux for 48 h more. After cooling, the reaction mixture was poured into water and extracted with ether (3 x 25 mL). The combined organic extract was washed with brine, dried (MgSO4) and concentrated. Purification of the residue by chromatography (petrol / ether, 6:4 to 4:6) gave, in order of elution, 2-(2-iodophenyl)ethyl thienylsulfone, 99, (0.71 g, 30%) as colourless needles. (mp 99-101C, CH2Cl2/petrol). Found C 38.2, H 2.9. C12H11IO2S2 requires C 38.1, H 2.9%. νmax (NaCl/film)/cm-1 3090, 1564, 1468, 1442, 1402, 1317, 1229, 1137, 1093, 1014, 856, 749; δH(400 MHz): 3.18 (2 H, m, CH2Ar), 3.45 (2 H, m, CH2S), 6.92 (1 H, dt, J 7.8 and 1.9, H-4), 7.19 (1 H, dd, J 4.8 and 3.8, H-4'), 7.22 (1 H, dd, J 7.8 and 1.9, H-6), 7.28 (1H, dt, J 7.5 and 1.4, H-5), 7.76 (1 H, dd, J 5.1 and 1.4, H-5'), 7.77 (1 H, dd, J 7.8 and 1.4, H-3), 7.78 (1 H, dd, J 3.8 and 1.3, H-3'); δC (100.6 MHz): 34.7 (CH2), 57.1 (CH2S), 99.8 (C), 128.0 (CH), 128.9 (CH), 129.0 (CH), 129.9 (CH), 134.3 (CH), 134.6 (CH), 139.6 (C), 139.8 (CH), 139.9 (C); m/z: 378 (M+, 1), 251 (41), 231 (20), 230 (100), 131 (18), 104 (60), 103 (70), 102 819), 78 (31), 77 (70); and starting methyl thienyl sulfone (0.49 g, 49%).
  • 16
  • [ 52260-00-1 ]
  • [ 62696-04-2 ]
  • [ 38695-60-2 ]
  • 17
  • [ 110-05-4 ]
  • [ 38945-01-6 ]
  • [ 38695-60-2 ]
YieldReaction ConditionsOperation in experiment
89% In water; at 100℃; for 10h;Sealed tube; In the reflux reactor,Followed by adding 0.5mmlSodium 2-thienylsulfinate,1 mmol di-tert-butyl peroxide,2.5mL water; magnetic stirring, heat sealed at 100 for 10 hours;After stopping heating, cool to room temperature and then use ethyl acetateThe reaction mixture was extracted three times; the ethyl acetate was removed under reduced pressure to obtain the target 2-thienylmethylsulfone.The structure of the resulting product was confirmed by GC-MS, 1H NMR, 13C NMR.The yield of 2-thienylmethylsulfone was 89%
89% With water; at 110℃; for 12h;Sealed tube; Green chemistry; General procedure: Sodium benzenesulfinate (0.5 mmol), 2-(tert-butylperoxy)-2-methylpropane (1 mmol), and H2O (2.5 mL) were added into a 10 mL sealed tube successively. Then, the reaction was carried out at 110 C under magnetic stirring for 12 h. After the reaction was finished, the reaction mixture was extracted with ethyl acetate for three times (5 mL × 3). The obtained organic layer was dried with anhydrous MgSO4. The solvent was removed under vacuum, and the obtained crude product was purified by silica gel column chromatography with petroleum ether/ethyl acetate (10:1) as eluent to afford the desired pure product.
  • 18
  • [ 38695-60-2 ]
  • [ 110-05-4 ]
  • 2-methyl-1-(thiophen-2-ylsulfonyl)propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In water; at 50℃; for 16h;Sealed tube; In a reflux reactor, 0.5 mml of sodium 2-thienylsulfinate, 1.5 mmol of di-tert-butyl peroxide,2.5mL of water; magnetic stirring, heating sealed at 50 for 16 hours; to stop heating, cooled to room temperature, and then with ethyl acetateThe reaction mixture was extracted three times; the ethyl acetate was removed under reduced pressure distillation to obtain the target product 2-methyl-1- (2-thiophene-phenylsulfonylYl) -2-propanol.The structure of the resulting product was confirmed by GC-MS, 1H NMR, 13C NMR and IR. 2-Methyl-1- (2-thiophenbenzenesulfonylYl) -2-propanol was isolated in 82% yield.
  • 19
  • [ 96-43-5 ]
  • [ 20277-69-4 ]
  • [ 38695-60-2 ]
  • 20
  • [ 74166-42-0 ]
  • [ 38695-60-2 ]
  • (+)-(R)-2-thienyl methyl sulfoxide [ No CAS ]
  • (R)-2-(methylsulfinyl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With manganese(II) triflate; 1-Adamantanecarboxylic acid; C32H38N4O2; dihydrogen peroxide; In water; acetonitrile; at -30 - 20℃; for 0.5h;Inert atmosphere; Resolution of racemate; General procedure: Mn(OTf)2 (1.4 mg, 0.004 mmol) and L2 (2.0 mg, 0.004 mmol) were dissolved in acetonitrile, and the mixture was stirred at room temperature for 12 h. To the solution of manganese complex were added substrate (0.4 mmol), 0.2 equiv of aca (14.4 mg, 0.08 mmol), and 49 % aqeous hydrogen peroxide (56.5 mg, 0.4 mmol). Then decreased the temperature to -30 C, and the reaction mixture was stirred at -30 C for 0.5 h. The aqueous was separated, the organic layer was dried over MgSO4, filtered, concentrated at reduced pressure. The product was purified by silica gel column chromatography to afford the corresponding sulfoxide and sulfone.
  • 21
  • [ 38695-60-2 ]
  • 2-((bromomethyl)sulfonyl)thiophene [ No CAS ]
  • 22
  • [ 38695-60-2 ]
  • 2-((dibromomethyl)sulfonyl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium phosphate; copper(l) iodide; C16H18N2O2; In dimethyl sulfoxide; at 120℃;Schlenk technique; Inert atmosphere; General procedure: Sodium alkylsulfinate or sodium arylsulfinate (6.5 mmol), copper iodide (0.5 mmol), ligand (0.5 mmol) and potassium phosphate (5.0 mmol) were added into a 10 mL Schlenk tube. The tube was evacuated and filled with argon for three times, and then aryl chloride (5 mmol) and 3 mL of DMSO were added. The reaction mixture was homogeneously stirred at 120 C. for 24-36 hours. After cooling, the contents of the of Schlenk tube were washed with ethyl acetate, and filtered through silica gel and diatomite plug. The filtrate was concentrated and purified by column chromatography to give the corresponding product.
  • 24
  • [ 3437-95-4 ]
  • [ 512-56-1 ]
  • [ 38695-60-2 ]
  • 25
  • [ 3437-95-4 ]
  • [ 616-42-2 ]
  • [ 38695-60-2 ]
YieldReaction ConditionsOperation in experiment
54% With bis-triphenylphosphine-palladium(II) chloride; 1,1,3,3-Tetramethyldisiloxane; tetrabutylammomium bromide; In 1,4-dioxane; at 120℃; for 18h;Inert atmosphere; 105.0 mg (0.5 mmol) of 2-iodothiophene, 550.3 mg (5 mmol) of dimethyl sulfite, 35.1 mg (0.05 mmol) of bistriphenylphosphorus palladium (II) dichloride, 100.7 mg (0.75 mmol) 1,1,3,3- tetramethyl disiloxane, 161.3 mg (0.5 mmol) of tetrabutylammonium bromide to the reaction tubes, 120OC was heated for 18 hours after the reaction was cooled, The filtrate was filtered and the filtrate was evaporated to remove the solvent. The residue was subjected to silica gel column chromatography, eluted with petroleum ether, TLC detection, and the effluent containing the product was combined. The solvent was distilled off by a rotary evaporator and dried under vacuum to obtain 43.8 mg of white solid 2-methyl. Sulfonylthiophene, the yield is 54%.
  • 26
  • [ 52260-00-1 ]
  • [ 868-85-9 ]
  • [ 38695-60-2 ]
YieldReaction ConditionsOperation in experiment
54% With sodium iodide; In 1,2-dimethoxyethane; water; at 65℃; General procedure: To a 10 mL round-bottom flask were added sulfonylhydrazine 1 (1.0 mmol), dimethyl phosphite 2 (0.6 mmol) and NaI (0.2 mmol) in mixed solvent DMF/H2O (10:1, v/v; 3 mL), and the solution was stirred for 5-10 h at 65 C until sulfonylhydrazine 1 was completely consumed as indicated by TLC analysis. The crude products were then concentrated under reduced pressure, and purified by flash column chromatography (petroleum ether/EtOAc = 30:1 to 10:1), to obtain pure products 3, 6 and 7 with 54-95% yield.
  • 27
  • [ 38695-60-2 ]
  • [ 73183-34-3 ]
  • [ 193978-23-3 ]
  • 28
  • [ 38695-60-2 ]
  • [ 106-89-8 ]
  • C8H9O3S2(1-)*Cl(1-)*Mg(2+) [ No CAS ]
  • 29
  • [ 38695-60-2 ]
  • [ 13067-79-3 ]
  • C9H11O3S2(1-)*Mg(2+)*Cl(1-) [ No CAS ]
 

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