Structure of 52010-97-6
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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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Stereoregular radical polymers enable selective spin transfer
Yeo, Hyunki ; Sorensen, Cole C ; Tahir, Hamas ; Marquardt, Andrew ; Yang, Yun-Fang ; Legaux, Nick , et al.
Abstract: Spintronic devices are emerging as an approach to realize performance and energy efficiency beyond what is possible with traditional electronic devices. State-of-the-art metals and doped conjugated polymers used for spin manipulation suffer from fundamental performance and stability issues. We leveraged stereoselective cationic polymerization to design a polymer with a stable persistent radical in each repeat unit that enables the longrange order necessary for spin transport. This approach overcomes conventional requirements for doping in organic spin-pumping devices while showcasing high conductivity, long spin-diffusion lengths, and processability. Molecular-level alterations in polymer stereochemistry were critical for controlling spin-spin interactions and alignment. Stereoregular polymers with persistent neutral radicals represent a previously unidentified class of materials for manipulating spins over long distances for applications in next-generation information storage.
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CAS No. : | 52010-97-6 |
Formula : | C8H8O2 |
M.W : | 136.15 |
SMILES Code : | OCC1=CC=C(C=O)C=C1 |
MDL No. : | MFCD11870191 |
InChI Key : | ZFHUHPNDGVGXMS-UHFFFAOYSA-N |
Pubchem ID : | 556330 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 37.96 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.39 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.08 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.84 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.85 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.83 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.97 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.95 |
Solubility | 15.4 mg/ml ; 0.113 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.25 |
Solubility | 76.3 mg/ml ; 0.56 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.14 |
Solubility | 0.977 mg/ml ; 0.00718 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) |
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) |
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 |
-7.19 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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 |
---|---|---|
49% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; | DIAD (0. [0195 MOL)] was added dropwise at a temperature between 0 and [5°C] to a mixture of 4-hydroxybenzaldehyde (0.015 mol), [5-HYDROXYMETHYL-1-METHYL-1H-] imidazole (CA No: 38993-84-9) (0.018 mol) and [PPH3] (0.0225 mol) in THF (40ml) under [N2] flow. The mixture was stirred at room temperature overnight, then stirred for a week end, diluted in EtOAc, extracted with [HC1] 3N, washed with EtOAc, alkalinized with [K2CO3] and extracted with EtOAc. The organic layer was separated, dried [(MGS04),] filtered, and the solvent was evaporated. Yielding: 1.6g of intermediate 38 (49percent). |
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