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Structure of 51792-34-8

Chemical Structure| 51792-34-8

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Product Details of [ 51792-34-8 ]

CAS No. :51792-34-8
Formula : C6H8O2S
M.W : 144.19
SMILES Code : COC1=CSC=C1OC
MDL No. :MFCD01096546
InChI Key :ZUDCKLVMBAXBIF-UHFFFAOYSA-N
Pubchem ID :3613501

Safety of [ 51792-34-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P264-P270-P301+P312-P330-P501

Computational Chemistry of [ 51792-34-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 5
Fraction Csp3 0.33
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 37.3
TPSA ?

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

46.7 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.16
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

1.54
Log Po/w (WLOGP)?

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

1.77
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.

0.45
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

2.48
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.68

Water Solubility

Log S (ESOL):?

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

-1.98
Solubility 1.5 mg/ml ; 0.0104 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.

-2.13
Solubility 1.07 mg/ml ; 0.00741 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

-1.9
Solubility 1.82 mg/ml ; 0.0126 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.

-6.09 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)

2.58

Application In Synthesis of [ 51792-34-8 ]

* 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 [ 51792-34-8 ]

[ 51792-34-8 ] Synthesis Path-Downstream   1~42

  • 1
  • [ 186581-53-3 ]
  • [ 14282-59-8 ]
  • [ 51792-34-8 ]
  • 2
  • [ 108-55-4 ]
  • [ 51792-34-8 ]
  • 5-(3,4-dimethoxy-[2]thienyl)-5-oxo-valeric acid [ No CAS ]
  • 3
  • [ 51792-34-8 ]
  • [ 98-88-4 ]
  • 3,4-bis-benzoyloxy-thiophene [ No CAS ]
  • 4
  • [ 51792-34-8 ]
  • [ 1490-25-1 ]
  • 4-(3,4-dimethoxy-[2]thienyl)-4-oxo-butyric acid [ No CAS ]
  • 5
  • [ 51792-34-8 ]
  • 3,4-dimethoxy-2,5-dinitro-thiophene [ No CAS ]
  • 6
  • [ 177364-96-4 ]
  • [ 51792-34-8 ]
YieldReaction ConditionsOperation in experiment
copper; In dimethyl sulfoxide; at 20 - 120℃; for 7.5h; [0034] 3,4-Dimethoxy-2,5-thiophenedicarboxylic acid (232 g) and copper powder (23 g) were added to DMSO (650 g) at room temperature. The reaction mixture was stirred under oxygen atmosphere for 30 minutes at room temperature and then heated at 120° C. for 7 hours. The reaction mixture was then poured into ice water (500 mL), and the crude product was extracted with ethyl acetate. After drying over anhydrous sodium sulfate, the solvent was removed by evaporation. The residue was vacuum-distilled at 50 mmHg to give 127 g of 3,4-ethylenedioxythiophene in high purity (96percent or higher). The purity was confirmed by gas chromatographic analysis. The chemical structure was confirmed by mass analysis and 1H-NMR.
  • 7
  • [ 3141-26-2 ]
  • [ 124-41-4 ]
  • [ 51792-34-8 ]
YieldReaction ConditionsOperation in experiment
81.5% With copper(I) bromide; In methanol; at 70 - 97℃;Inert atmosphere; 21 g of sodium methoxide and 72 g of methanol were added to a 100 ml four-necked flask (the concentration of sodium methoxide relative to the methanol solvent was 22.6percent by weight based on the total amount of sodium methoxide before the reaction) and dissolved at 70 under an argon atmosphere.After addition of 0.83 g of cuprous bromide, 15 g of 3,4-dibromothiophene was added dropwise, and the reaction solution became colorless transparent to black. After completion of the dropwise addition, 50 g of methanol was distilled off (sodium methoxide to methanol solvent The concentration was 48.8 wtpercent based on the total amount of sodium methoxide before the reaction)The reaction was heated to reflux at 97 .When the reaction was traced by gas chromatography, 3,4-dibromothiophene and 3-bromo-4-methoxythiophene were found to be below the detection limit at the reflux starting time of 5 hours.After water was added to the reaction mixture and the mixture was filtered, the crude product was extracted from toluene, and the toluene layer was washed with water, and then the toluene layer was dried with magnesium sulfate.After the magnesium sulfate was removed by filtration, the toluene layer was concentrated by a rotary evaporator and then subjected to vacuum distillation to obtain 7.28 g (yield: 81.5percent) of 3,4-dimethoxythiophene. The purity of its 3,4-dimethoxythiophene was 98.01percent by gas chromatography.The purity (concentration) by gas chromatography in the present invention was indicated by the area ratio of the peak area obtained by the detection device by FID using Agilent 6890N network GC manufactured by Aglient Technologies.
60% With copper(l) iodide; In methanol; at 80℃; for 72h; Step 3: 3,4-dibromothiophene (10 g, 41.2 mmol) is added to 30 g of a methanol-sodium methoxide solution with a mass percent of 30percent and stirred. Then CuI (1.96 g, 10.3 mmol) is added quickly, and refluxed at 80° C. for 72 hrs. The mixture is cooled to room temperature, to which a saturated NaCl solution is added. The mixture is extracted with ethyl acetate several times, and dried over anhydrous sodium sulfate to remove solvents. The crude is passed through a separation column, to give a oily liquid, 3,4-dimethoxythiophene (compound 3), yield 60percent, purity 95percent.
  • 8
  • [ 51792-34-8 ]
  • [ 34446-64-5 ]
  • [ 95602-75-8 ]
  • 9
  • [ 1121-60-4 ]
  • [ 51792-34-8 ]
  • (3,4-dimethoxy-2-thienyl)-2-pyridylmethanol [ No CAS ]
  • 10
  • [ 500-22-1 ]
  • [ 51792-34-8 ]
  • (3,4-dimethoxy-2-thienyl)-3-pyridylmethanol [ No CAS ]
  • 11
  • [ 51792-34-8 ]
  • [ 71046-35-0 ]
  • (3,4-dimethoxy-2-thienyl)-(6,7-dimethoxy-1-isoquinolyl)methanol [ No CAS ]
  • 12
  • [ 51792-34-8 ]
  • [ 124-38-9 ]
  • 3,4-dimethoxythiophene-2-carboxylic acid [ No CAS ]
  • 13
  • [ 51792-34-8 ]
  • 2-bromo-3,4-dimethoxythiophene [ No CAS ]
  • 14
  • [ 177364-96-4 ]
  • [ 51792-34-8 ]
  • 3,4-dimethoxythiophene-2-carboxylic acid [ No CAS ]
  • 3-hydroxy-4-methoxythiophene [ No CAS ]
  • 3,4-Dimethoxy-thiophene-2-carboxylic acid methyl ester [ No CAS ]
  • 16
  • [ 51792-34-8 ]
  • [ 20089-07-0 ]
  • 3,4-bis[(S)-2-methylbutylthio]thiophene [ No CAS ]
  • 17
  • [ 51792-34-8 ]
  • [ 109-79-5 ]
  • [ 211236-84-9 ]
  • 20
  • [ 51792-34-8 ]
  • 2-methyl-butanethiol [ No CAS ]
  • 3,4-bis(2-methylbutylthio)thiophene [ No CAS ]
  • 21
  • [ 51792-34-8 ]
  • [ 112-55-0 ]
  • 3,4-bis(n-dodecylthio)thiophene [ No CAS ]
  • 24
  • [ 51792-34-8 ]
  • [ 1565-80-6 ]
  • [ 188947-38-8 ]
  • 25
  • [ 110-89-4 ]
  • [ 51792-34-8 ]
  • [ 50-00-0 ]
  • [ 403700-09-4 ]
  • 26
  • [ 110-91-8 ]
  • [ 51792-34-8 ]
  • [ 50-00-0 ]
  • N-[(3,4-dimethoxythien-2-yl)methyl]morpholine [ No CAS ]
  • 27
  • [ 110-91-8 ]
  • [ 51792-34-8 ]
  • [ 50-00-0 ]
  • N-[(3,4-dimethoxythien-2-yl)methyl]morpholine [ No CAS ]
  • 2,5-bis(morpholin-4-ylmethyl)-3,4-dimethoxythiophene [ No CAS ]
  • 28
  • [ 51792-34-8 ]
  • [ 50-00-0 ]
  • [ 124-40-3 ]
  • N-[(3,4-dimethoxythien-2-yl)methyl]-N,N-dimethylamine [ No CAS ]
  • 29
  • [ 51792-34-8 ]
  • [ 815-24-7 ]
  • 2,2,4,4-tetramethyl-3-[2-(3,4-dimethoxythienyl)]pentan-3-ol [ No CAS ]
  • 33
  • [ 51792-34-8 ]
  • [ 112-53-8 ]
  • [ 496800-96-5 ]
  • 34
  • [ 51792-34-8 ]
  • [ 31482-45-8 ]
  • (3,4-dimethoxy-2-thienyl)(1-adamantyl)(tert-butyl)methanol [ No CAS ]
  • 35
  • [ 51792-34-8 ]
  • [ 71-36-3 ]
  • [ 126673-34-5 ]
  • 36
  • [ 51792-34-8 ]
  • [ 129119-29-5 ]
  • C18H24N2O2S7(2+)*2F6P(1-) [ No CAS ]
  • 37
  • [ 51792-34-8 ]
  • [ 77-85-0 ]
  • [ 426263-16-3 ]
YieldReaction ConditionsOperation in experiment
toluene-4-sulfonic acid; In toluene; at 100℃; for 48h; Synthesis of (3-methyl-3,4-dihydro-2H-thieno[3,4-b][1 ,4]dioxepin-3-yl)-methanol; <strong>[51792-34-8]3,4-dimethoxythiophene</strong> (4 g, 27.8 mmol) was taken with 1500 mL of toluene and to this trimethylol ethane (4.32 g, 36.10 mmol) was added followed by p-TSA (0.52 g, 2.78 mmol). The mixture was stirred at 100 0C with a continuous flow of argon for 48 h. Excess toluene was evaporated and the greenish black residue was extracted with ethyl acetate, washed repeatedly with water, dried over sodium sulphate and ethyl acetate was removed under vacuum. The crude product was purified by silica gel column chromatography eluting with pet ether-ethyl acetate (80:20) to get colourless viscous oil which solidified over a period of two days to a white solid. 1H NMR (CDCI3): 0.95 (s, 3H), 1.70 (s, 1H), 3.73 (d, 2H), 3.74 (s, 2H), 4.08 (d, 2H), 6.48 (s, 2H). Mass: 200 [M]+
With toluene-4-sulfonic acid; In toluene; at 110℃; for 36h; ProDOT-OH and ProDOT-N3 were synthesized as described inthe literature [35]. 3-Methyl-3-(hydroxymethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine, ProDOT-OH: <strong>[51792-34-8]3,4-dimethoxythiophene</strong> (2.5 g,17.5 mmol) was dissolved in 100 mL of toluene. 2-Hydroxymethyl-2-methylpropan-1,3-diol (4.2 g, 2 eq, 35 mmol) and para-toluenesulfonic acid monohydrate (635 mg, 0.2 eq, 3.5 mmol) were added. The mixture was warmed at 110 °C over 36 h. The mixture was allowed to cool at room temperature. The toluene phase was extracted with NaHCO3 5 percent in water (230 mL) and brine (30 mL), and finally dried (Na2SO4). The solvents were removed under reduced pressure. The compound was finallypurified on column (8/2, cyclohexane/ethyl acetate). 3-(Azidomethyl)-3-methyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine, ProDOT-N3: ProDOT-OH (2.6 g, 11.5 mmol) wasdissolved in 50 mL of dichloromethane. Triethylamine (2.3 g, 2eq, 23 mmol) was added. The mixture was cooled at 0 C.Methanesulfonyl chloride (1.58 g, 1.2 eq, 13.8 mmol) was addeddropwise. The mixture was allowed to warm up at room temperature. After 4 h, 10 mL of methanol was added. The mixture was stirred for 30 additional min. All volatiles were removed under reduced pressure. The residual oil was dissolved in 100 mL of N,N-dimethylformamide (DMF) and NaN3 (3.7 g, 5 eq, 44.5 mmol) was added. The mixture was heated at 95 °C overnight. The reaction was then allowed to cool at room temperature and most part of the DMF was removed under reduced pressure. 100 mL of dichloromethane was added. The organic layer was washed with water (230 mL) and brine (30 mL), dried over Na2SO4. The solvents were removed under reduced pressure. ProDOT-1N3 is finally purified on column (80/20, cyclohexane/dichloromethane). All yields and spectroscopic data agreed with the literature.
  • 38
  • [ 51792-34-8 ]
  • [ 107-21-1 ]
  • [ 126213-50-1 ]
YieldReaction ConditionsOperation in experiment
46.7% With toluene-4-sulfonic acid; In methanol; toluene; at 100℃; for 3h;Inert atmosphere; The following production was carried out using <strong>[51792-34-8]3,4-dimethoxythiophene</strong> prepared by the same production method as in Example 2 described above. This also applies to Examples 5 to 9 and Comparative Examples 3 to 9 described below.First, 10.1 g of <strong>[51792-34-8]3,4-dimethoxythiophene</strong>, 6.74 g of ethylene glycol, 1.1 g of p-toluenesulfonic acid monohydrate and 76.6 g of toluene were placed in a 100 ml four-necked flask, and the mixture was heated and stirred in an argon atmosphere.And heated to 100 DEG C while distilling methanol at 95 deg. At 100 , the methanol flow terminated and toluene reflux started.The compositional change in the reaction solution was followed by gas chromatography using N, N-dimethylformamide as an internal standard. As a result, <strong>[51792-34-8]3,4-dimethoxythiophene</strong> was found to be below the detection limit at the reflux time of 3 hours. Table 1 summarizes the relationship between the time from the start of reflux of toluene and the concentration of each component.The EDOT, DMEOT, mono- and di-substituents in Table 1 are3,4-ethylenedioxythiophene,<strong>[51792-34-8]3,4-dimethoxythiophene</strong>,One in which one methoxy group of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> is substituted with ethylene glycol,And methoxy groups of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> were replaced with ethylene glycol The conversion (percent) in the table is theoretically 3, 4-ethylenedioxythiophene when N, N-dimethoxyformamide is measured by gas chromatography as an internal standard, Represents the ratio of the amount of 4-ethylenedioxythiophene.The residual ratio (percent) likewise represents the ratio of the actual amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in the reaction solution to the amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in theory.The reaction mixture was diluted with water, the insoluble material was removed by filtration, the crude product was extracted from toluene, the toluene layer was washed with water, washed with aqueous sodium hydrogencarbonate solution, and then dried with magnesium sulfate.After the magnesium sulfate was removed by filtration, the toluene layer was concentrated on a rotary evaporator to obtain a crude product.The yield of the crude product was 6.78 g (68.1percent) and the purity was 98.69percent by gas chromatography.The crude product was subjected to vacuum distillation to obtain 4.65 g (yield: 46.7percent) of 3,4-ethylenedioxythiophene. The purity of its 3,4-ethylenedioxythiophene was 99.64percent by gas chromatography.
  • 39
  • [ 3588-31-6 ]
  • [ 51792-34-8 ]
  • 40
  • [ 51792-34-8 ]
  • [ 1792-81-0 ]
  • (4aR,8aS)-4a,5,6,7,8,8a-Hexahydro-4,9-dioxa-2-thia-cyclopenta[b]naphthalene [ No CAS ]
  • 41
  • [ 51792-34-8 ]
  • [ 57794-08-8 ]
  • (4aS,8aS)-4a,5,6,7,8,8a-Hexahydro-4,9-dioxa-2-thia-cyclopenta[b]naphthalene [ No CAS ]
  • 42
  • [ 51792-34-8 ]
  • [ 1029272-42-1 ]
  • (2S,3R)-2,3-Dimethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 51792-34-8 ]

Ethers

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A298852 [17573-92-1]

3-Methoxythiophene

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2,5-Dimethoxythiophene

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