Structure of 466639-53-2
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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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Structure-Activity Relationships for Hypervalent Iodine Electrocatalysis
Frey, Brandon L. ; Thai, Phong ; Patel, Lauv ; Powers, David C. ;
Abstract: The design and optimization of novel electrocatalysts requires robust structure-activity data to correlate catalyst structure with electrochem. behavior. Aryl iodides have been gaining attention as metal-free electrocatalysts but exptl. data are available for only a limited set of structures. Herein we report electrochem. data for a family of 70 aryl iodides. Half-peak potentials are utilized as proxies for reduction potentials and reveal that, despite differences in electrochem. reversibility, the potential for one-electron oxidation of 4-substituted aryl iodides to the corresponding iodanyl radicals is well-correlated with standard Hammett parameters. Addnl. data are presented for 3- and 2-substituted aryl iodides, including structures with potentially chelating 2-substituents that are commonly encountered in hypervalent iodine reagents. Finally, potential decomposition processes relevant to the (in)stability of iodanyl radicals are presented. We anticipate that the collected data will advance the design and application of aryl iodide electrocatalysis.
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Keywords: hypervalent iodine ; electrochemistry ; linear free-energy relationships ; sustainable catalysis ; oxidation
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CAS No. : | 466639-53-2 |
Formula : | C7H6BrIO |
M.W : | 312.93 |
SMILES Code : | COC1=CC(Br)=C(I)C=C1 |
MDL No. : | MFCD12547848 |
InChI Key : | DIQUDEJWQWDXHP-UHFFFAOYSA-N |
Pubchem ID : | 49757975 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 53.35 |
TPSA ? Topological Polar Surface Area: Calculated from |
9.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.55 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.23 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.06 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.44 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.47 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.15 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.19 |
Solubility | 0.0201 mg/ml ; 0.0000641 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.1 |
Solubility | 0.25 mg/ml ; 0.0008 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.31 |
Solubility | 0.0153 mg/ml ; 0.000049 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 |
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) |
Yes |
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) |
Yes |
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 |
-5.92 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 |
0.55 |
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) |
2.32 |
* 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 |
---|---|---|
72% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 5h; | (2) Synthesis of Intermediate 1-2 2.5 g (10.0 mmol) of Intermediate 1-1, 3.4 g (11.0 mmol) of 2-bromo-1-iodo-4-methoxy benzene, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 2.1 g (15.0 mmol) of K2CO3 were dissolved in 40 mL of a mixed solution of THF and H2O (2:1 by volume) and stirred at about 80 C. for about 5 hours. After the resulting reaction solution was cooled down to ambient temperature, 40 mL of water was added thereto, followed by extraction three times with 50 mL of diethyl ether. An organic phase was collected and dried using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified by silica gel column chromatography to obtain 2.3 g of Intermediate 1-2 (Yield: 72%). This compound was identified by LC-MS. C17H13BrO M+ 313.1 |
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