Structure of 5683-31-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 5683-31-8 |
Formula : | C6H10O2Si |
M.W : | 142.23 |
SMILES Code : | C[Si](C)(C)C#CC(O)=O |
MDL No. : | MFCD00190216 |
InChI Key : | IPEATTYBFBRNEB-UHFFFAOYSA-N |
Pubchem ID : | 2760863 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.5 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 38.76 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.76 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.22 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.03 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.17 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.76 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.08 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.12 |
Solubility | 1.08 mg/ml ; 0.00758 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.64 |
Solubility | 0.327 mg/ml ; 0.0023 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.58 |
Solubility | 37.7 mg/ml ; 0.265 mol/l |
Class? Solubility class: Log S scale |
Soluble |
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) |
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 |
-5.59 cm/s |
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 |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 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) |
3.31 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0℃; for 0.25h; | In a 10 mL flask, the <strong>[5683-31-8]3-(trimethylsilyl)propiolic acid</strong> (3.24 mmol, 0.460 g) was dissolved in dry DCM (1 mL) under argon atmosphere. Oxalyl chloride (3.24 mmol, 0.27 mL) and DMF (0.03 mL) were successively added to the reaction mixture at 0C. After 15 minutes of stirring, the apparition of bubbles stopped. Oxalyl chloride and DCM were evaporated under vacuum. (0115) To a solution of this resulting 100 3-(trimethylsilyl)propynoyl chloride in dry 8 DCM (1 mL) were added dropwise at 0C 33 4-amino-N-(2,5-dimethoxyphenyl) benzenesulfonamide (1.62 mmol, 0.500 g) dissolved in 11 mL of dry DCM and 49 Et3N (0.23 mL, 1.62 mmol). After stirring overnight, the reaction mixture was quenched with a saturated solution of 13 NaCl. The aqueous layer was extracted three times with DCM. The combined organic layers were dried over Na2SO4. After removal under vacuum of the solvent, the crude was purified by chromatography over silica gel (DCM/EP: 60/40 to 100/0) affording the expected 96 compound (28) as a white solid (0.45 g, 1.04 mmol) with 64% yield. (Rf: 0.29 (DCM); mp: 84C). RMN 1H (300 MHz, CDCl3): 7.74 (d, 2H, Har), 7.58 (s, 1 H, NH), 7.56 (d, 2H, Har), 7.15 (d, 1 H, H7), 7.01 (s, 1 H, NH), 6.65 (d, 1H, H5), 6.56 (dd, 1 H, H6), 3.75 (s, 3H, CH3), 3.60 (s, 3H, CH3), 0.25 (s, 9H, Si-CH3). RMN 13C (75 MHz, CDCl3): 154.0 (s, CO), 150.3 (s, CO), 143.7 (s, CO), 141.3 (s, Car), 134.8 (s, Car), 128.8 (s, Car), 126.5 (s, Car), 119.3 (s, Car), 111.6 (s, C5), 110.1 (s, C6), 107.4 (s, C7), 97.3 (s, Calk), 94.4 (s, Calk), 56.3 (s, CH3), 55.9 (s, CH3), -0.67 (s, Si-CH3). HRMS: Calculated for [M+ H]+: 433.1253; Measured: 433.1248. IR: 3232 (v N-H), 2956 (v Car-H), 2835 (v OC-H), 1648 (v C=O), 1313 (vas SO2), 1152 (vs SO2) | |
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0℃; for 0.25h;Inert atmosphere; | In a 10 mL flask, the <strong>[5683-31-8]3-(trimethylsilyl)propiolic acid</strong> (3.24 mmol, 0.460 g) was dissolved in dry DCM (1 mL) underargon atmosphere. Oxalyl chloride (3.24 mmol, 0.27 mL) and DMF (0.03 mL) were successively added to the reactionmixture at 0C. After 15 minutes of stirring, the apparition of bubbles stopped. Oxalyl chloride and DCM were evaporatedunder vacuum. | |
With oxalyl dichloride; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.5h; | [1435] 3-(trimethylsilyl)propioloyl chloride : To a stirred solution of <strong>[5683-31-8]3-(trimethylsilyl)propiolic acid</strong> (0.080 g, 0.562 mmol, 1 eq) in DMF (0.002 mL, 0.022 mmol, 0.04 eq) was added oxalyl chloride (0.053 mL, 0618 mmol, 1.1 eq) at 0C. The mixture was allowed to warm room temperature and stirred 30 minutes. Then, the reaction mixture was concentrated under reduced pressure to obtain 3-(trimethylsilyl)propioloyl chloride. The crude was taken as such to next step. |