Cat.NO.:A118049 Purity:98%
Product Details of [ 100342-30-1 ]
CAS No. : | 100342-30-1 |
Formula : |
C8H13NO2S2 |
M.W : |
219.32
|
SMILES Code : | C(C)(C)(C)N[S](=O)(=O)C1=CC=CS1 |
MDL No. : | MFCD02047252 |
InChI Key : | CLKMBGGZGFULOO-UHFFFAOYSA-N |
Pubchem ID : | 765814 |
Safety of [ 100342-30-1 ]
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P305+P351+P338 |
Computational Chemistry of [ 100342-30-1 ] Show Less
Physicochemical Properties
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.5 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 54.67 |
TPSA ?
Topological Polar Surface Area: Calculated from |
82.79 Ų |
Lipophilicity
Log Po/w (iLOGP)?
iLOGP: in-house physics-based method implemented from |
1.69 |
Log Po/w (XLOGP3)?
XLOGP3: Atomistic and knowledge-based method calculated by |
1.09 |
Log Po/w (WLOGP)?
WLOGP: Atomistic method implemented from |
2.91 |
Log Po/w (MLOGP)?
MLOGP: Topological method implemented from |
0.62 |
Log Po/w (SILICOS-IT)?
SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.7 |
Consensus Log Po/w?
Consensus Log Po/w: Average of all five predictions |
1.6 |
Water Solubility
Log S (ESOL):?
ESOL: Topological method implemented from |
-1.97 |
Solubility | 2.33 mg/ml ; 0.0106 mol/l |
Class?
Solubility class: Log S scale |
Very soluble |
Log S (Ali)?
Ali: Topological method implemented from |
-2.42 |
Solubility | 0.832 mg/ml ; 0.00379 mol/l |
Class?
Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)?
SILICOS-IT: Fragmental method calculated by |
-2.86 |
Solubility | 0.302 mg/ml ; 0.00138 mol/l |
Class?
Solubility class: Log S scale |
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) |
No |
CYP1A2 inhibitor?
Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor?
Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor?
Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor?
Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor?
Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)?
Skin permeation: QSPR model implemented from |
-6.86 cm/s |
Druglikeness
Lipinski?
Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose?
Ghose filter: implemented from |
None |
Veber?
Veber (GSK) filter: implemented from |
0.0 |
Egan?
Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge?
Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score?
Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
Medicinal Chemistry
PAINS?
Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk?
Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness?
Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility?
Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.84 |
Application In Synthesis of [ 100342-30-1 ]
* 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 [ 100342-30-1 ]
[ 100342-30-1 ] Synthesis Path-Downstream 1~24
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In ethyl acetate; | EXAMPLE 1 5-butyl-<strong>[100342-30-1]2-(N-t-butylaminosulfonyl)thiophene</strong> To a solution of <strong>[100342-30-1]2-(N-t-butylaminosulfonyl)thiophene</strong> (2.01 g, 9.18 mmol) in anhydrous THF (17 mL) cooled to -78 C. under N2 was added 2.5 M n-BuLi (10 mL, 2.7 equiv). After stirring at -78 C. for 30 min the bath temperature was raised to -40 C. and the mixture was stirred for an additional 2 hrs. To this mixure was added n-butyliodide (2.0 mL, 2 equiv) and the reaction was allowed to warm to room temperature. After stirring overnight the darkened reaction mixture was quenched with NH4 Cl soln and extracted with EtOAc. The organic was washed with brine and dried over anhydrous MgSO4 and concentrated in vacuo. The titled compound was purified by flash chromatography eluding with hex/EtOAc (15:1 to 7:1). Rf=0.32 (6:1 Hex/EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.62 g (94%) | In tetrahydrofuran; | Step A: N-(1,1-Dimethylethyl)-2-thiophenesulfonamide To a solution of t-butylamine (8.35 g, 0.114 mol) in dry tetrahydrofuran (THF) (20 mL) cooled to 0 C. was added dropwise 2-thiophenesulfonyl chloride (5.0 g, 27.4 mmol). After the addition was completed, the reaction mixture was warmed to ambient temperature and stirred overnight. The mixture was extracted with ethyl acetate (3*80 mL) and the combined extracts were washed with water, dried over molecular sieves and concentrated. The residue was chromatographed on (silica, eluding with 25% ethyl acetate-hexane) to yield 5.62 g (94%) of solid: mp 80-82 C. |
5.62 g (94%) | In tetrahydrofuran; | Step A: N-(1,1-Dimethylethyl)-2-thiophenesulfonamide To a solution of t-butylamine (8.35 g, 0.114 mol) in dry tetrahydrofuran (THF) (20 mL) cooled to 0 C. was added dropwise 2-thiophenesulfonyl chloride (5.0 g, 27.4 mmol). After the addition was completed, the reaction mixture was warmed to ambient temperature and stirred overnight. The mixture was extracted with ethyl acetate (3*80 mL) and the combined extracts were washed with water, dried over molecular sieves and concentrated. The residue was chromatographed on silica, eluding with 25% ethyl acetate-hexane, to yield 5.62 g (94%) of solid: mp 80-82 C. |
In chloroform; at 0 – 20℃; for 1.16667h;Heating / reflux; | Thiophene-2-sulfonyl chloride (15 g, 0.082 mol) was dissolved in CHC13 (200 mL) under N2 atmosphere and then cooled to 0C. tert-Butylamine (25.9 mL, 0.246 mol) dissolved in CHC13 (50 mL) was then added dropwise to the reaction mixture. The reaction mixture was stirred for 1 h at room temperature and then at reflux for 10 min. Toluene (700 mL) was added and the organic phase was washed with water (3 x 50 mL), dried, and concentrated in vacuo. The sub-title product was used without further purification in the next step. IH NMR B (CDC13) : 7.60 (1H, dd, J= 1.3, 3.8 Hz), 7.53 (1H, dd, J= 1.3, 5.0 Hz), 7.02 (1H, dd, J = 5. 0,3. 8 Hz), 5.13 (1H, m), 1.24 (9H, m) 13C NMR B (CDC13) : 145.0, 131.7, 131.2, 127.0, 55.1, 29.9 |
In chloroform; at 0℃; for 1.16667h;Heating / reflux; | Thiophene-2-sulfonyl chloride (15 g, 0.082 mol) was dissolved in CHC13 (200 mL) under N2 atmosphere and then cooled to 0C. TERT-BUTYLAMINE (25.9 mL, 0.246 mol) dissolved in CHC13 (50 ML) was then added dropwise to the reaction mixture. The reaction mixture was stirred for 1 hour at room temperature and then at reflux for 10 min. Toluene (700 mL) was added and the organic phase was washed with water (3 x 50 mL), dried, and concentrated in vacuo. The sub-title product was used without further purification in the next step. 1H NMR No.(CDCL3) : 7.60 (1H, dd, J= 1.3, 3.8 Hz), 7.53 (1H, dd, J= 1.3, 5.0 Hz), 7.02 (1H, dd, J = 5.0, 3.8 Hz), 5. 13- (1 H, m), 1.24 (9H, m) 13C NMR 6 (CDC13) : 145.0, 131.7, 131.2, 127.0, 55.1, 29.9 | |
In chloroform; at 20℃; for 1.16667h;Heating / reflux; | Thiophene-2-sulfonyl chloride (15 g, 0.082 mol) was dissolved in CHC13 (200 mL) under N2 atmosphere and then cooled to 0C. tert-Butylamine (25.9 mL, 0.246 mol) dissolved in CHC13 (50 ML) was then added dropwise to the reaction mixture. The reaction mixture was stirred for 1 h at room temperature and then at reflux for 10 min. Toluene (700 mL) was added and the organic phase was wa
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