Structure of 108847-76-3
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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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Asif, Nehal ;
Abstract: This study investigates the development and application of organocatalysts for the reduction of CO2 under mild and sustainable conditions. A key focus is the synthesis of an organo-boronic acid–amine catalyst system (derived from thianthren-1-ylboronic acid and diethanolamine) and its subsequent evaluation in reactions with labeled CO2. Through NMR analyses, including time-resolved monitoring of isotopically labeled substrates, the formation of formyl intermediates and downstream products such as formate and methoxy species was confirmed, demonstrating active CO2 transformation. Multiple catalyst variants (NA1 series) were screened to assess activity and selectivity, with experimental conditions optimized in terms of temperature, solvent selection, and the use of boron-based reductants (HBpin). Complementary electrochemical approaches using amine co-substrates (isopropylamine, diisopropylamine, and methylpiperazine) were also explored, broadening the scope of potential pathways for carbon capture and conversion. Together, these results highlight the versatility, cost-effectiveness, and reduced environmental impact of organocatalyst-mediated processes compared to conventional metal-based routes. The research thus provides a foundational framework for further optimizing organocatalytic CO2 reduction and underscores the promise of these catalysts for sustainable chemical transformations.
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CAS No. : | 108847-76-3 |
Formula : | C12H9BO2S2 |
M.W : | 260.14 |
SMILES Code : | OB(O)C1=C2SC3=CC=CC=C3SC2=CC=C1 |
MDL No. : | MFCD00093039 |
InChI Key : | FZEWPLIHPXGNTB-UHFFFAOYSA-N |
Pubchem ID : | 2734382 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 70.96 |
TPSA ? Topological Polar Surface Area: Calculated from |
91.06 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.04 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.98 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.56 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.44 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.8 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.82 |
Solubility | 0.039 mg/ml ; 0.00015 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.62 |
Solubility | 0.00627 mg/ml ; 0.0000241 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.02 |
Solubility | 0.0247 mg/ml ; 0.0000948 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
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) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.73 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 |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.98 |
* 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 |
---|---|---|
92% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃; for 8h;Inert atmosphere; | Thianthrene-1-boronic acid 20g (76.88mmol), <strong>[57381-62-1]methyl-2-bromo-4-chlorobenzoate</strong>21.1 g (84.57mmol) and tetrakis triphenylphosphinepalladium 0.89g (0.769mmol) were placed in a flask, and under a nitrogen atmosphere, it was dissolved in tetrahydrofuran 257 ml, and then an aqueous solution 128ml of dissolved potassium carbonate 17g (115.3mmol) was added, and stirred at reflux at 70 ° Cfor 8 h. After completion of the reaction, it was extracted with ethyl acetate,the extract was dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gelcolumn chromatography using n-hexane / ethyl acetate (9: 1 volume ratio) toobtain intermediate M-28 of the desired compound 27.2 g (92percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; for 15h;Inert atmosphere; Reflux; | Under nitrogen atmosphere, 3,6-dibromo-9-phenyl-9H- carbazole 4.0g (10mmol) ,thianthren-1-ylboronic acid 6.5g (25mmol) was dissolved in toluene 50ml and Pd(PPh3) 4 0.5g (0.5mmol), 2M K2CO3 30ml (60mmol) was added and refluxed for 15 hours. After the reaction is complete, the temperature of the reaction was cooled to room temperature, toluene 300ml H2O and 300ml of water was added and the organic layer was extracted, concentrated and filtered under reduced pressure, then it was dried over anhydrous MgSO4, and separated by column chromatography using Hex: MC = 3:1 to give the compound 31 5.04g (75percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; In tetrahydrofuran; water; at 80℃; for 3h;Inert atmosphere; | general procedure for Suzuki cross-coupling reaction. Adried 100 mL flask was charged with 1-thianthrenyl boronic acid (1.0equiv.), bromoaryl derivative (1.0 equiv.), bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh3)2Cl2, 0.05 equiv.), and powderedpotassium hydroxide (5 equiv.). The reaction vessel was vacuumed andfiled with argon. Degassed tetrahydrofuran (THF) and degassed waterwere added, and the reaction mixture was stirred at 80 C for 3 h. Thecrude product was extracted into DCM, and the organic phase waswashed with water and dried over Na2SO4. The solvent was removedand the residue was purified by column chromatography using hexane/ethyl acetate (6/1) as eluent. The target product was crystallized fromthe eluent.4-Bromo-4?-thianthrene-1-yl-benzophenone (Br-BP-TA) was preparedby method A from 1-thianthrenyl boronic acid (0.38 g, 1.47 mmol),4,4?-dibromobenzophenone (0.50 g, 1.47 mmol), Pd(PPh3)2Cl2 (0.05 g,0.07 mmol), KOH (0.41 g, 7.35 mmol), 10 mL of THF and 2 mL of waterwere used. The yield of white crystals (fw=474 g/mol,mp=138-139 C) was 76%.1H NMR (400 MHz, CDCl3), delta (ppm): 7.82 (d, J=8.2 Hz, 2H, Ar),7.69 (d, J=8.5 Hz, 2H, Ar), 7.60 (d, J=8.5 Hz 2H, Ar), 7.42-7.50 (m,4H, Ar), 7.30 (dd, J=7.5, 1.4 Hz, 1H, Ar), 7.10-7.26 (m, 4H, Ar).13C NMR (100 MHz, CDCl3), delta (ppm): 195.23, 144.59, 141.29,136.35, 136.32, 136.21, 136.07, 135.51, 134.90, 131.72, 131.59,129.92, 129.62, 129.07, 128.89, 128.84, 128.62, 127.97, 127.70,127.61, 127.28.IR numax in cm-1: (CH Ar) 3087, 3068, 3051; (C=O) 1647; (C=CAr) 1480; (CH Ar) 929, 857; (CS) 746; (CBr) 634.MS (APCI+, 20V), m/z (%): 475 ([M+H]+, 100)Elemental analysis. Calcd. for C25H15BrOS2 (%): C 63.16, H 3.18, Br16.81, O 3.37, S 13.49. Found (%): C 63.17, H 3.23, O 3.44. |
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