Structure of 10240-08-1
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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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Accessing Arenes via the Hydrodeoxygenation of Phenolic Derivatives Enabled by Hydrazine
Di Erasmo, Benedetta ; Perepichka, Inna ; Su, Hui ; Vaccaro, Luigi ; Li, Chao-Jun ;
Abstract: Hydrodeoxygenation (HDO) is an effective method for converting lignin and its derived phenolic compounds to value-added aromatic chemicals and fuels. Efforts to exploit molecular hydrogen have been made to remove the hydroxyl group in lignin-derived phenolic compounds to make them appealing for the chemical industry. However, these processes rely on high pressure and expensive catalysts, presenting challenges in terms of safety, hydrogen storage, and cost-effectiveness. This highlights the demand for alternatives under more accessible reaction conditions. Herein, we present a methodology for the HDO of phenols and naphthols using Pd/C as a commercial heterogeneous catalyst employing hydrazine as a dual reagent for reducing and hydrazone formation. This paper presents an applicable substrate scope for the HDO of different naphthols and phenols including pharmaceutically relevant molecules such as paracetamol. Additionally, highly challenging steroid derivatives, such as β-estradiol, have been hydrodeoxygenated.
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Keywords: hydrodeoxygenation ; phenols ; heterogeneous catalyst ; hydrazone ; arenes ; palladium
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Jones, Jordan Anthony ;
Abstract: Part I: Resonance assisted hydrogen bonds (RAHBs) are among the strongest forms of hydrogen bonding known to occur and are found in specific intramolecular hydrogenbonding systems. Two series of ortho-acylnaphthols that undergo this type of hydrogen bonding were synthesized. One series was substituted on the 4-naphthol position (Y), and the other substituted on the p-benzoyl position (X), where X or Y = OCH3, CH3, H, Br, Cl, or NO2. A Hammett study was carried out using 1H NMR and 13C NMR to determine the nature of the electronic effects on the RAHB in this system. Previous research has shown that pbenzoyl substituents cause the enolic 1H NMR shift to increase when electron-donating groups are in the para position, exhibiting shifts up to 14.01ppm. The opposite trend has now been observed with 4-naphthyl substituents; the enolic 1H NMR shift increased as the electron-withdrawing character of the substituent increased, exhibiting shifts up to 14.60ppm. Part II: A computational chemistry exercise intended for second-semester general chemistry students has been developed and used in the laboratory curriculum at a regional university. Students used the Avogadro software to build, optimize, and measure bond lengths and angles in simple organic molecules, focusing on the functional groups. The exercise was used as an out-of-class exercise for students to review VSEPR theory while simultaneously introducing them to organic functional groups and computational chemistry fundamentals. A pre-test and post-test were used to evaluate the educational efficacy of the exercise, and a survey was conducted to determine if students found the exercise helpful. Data from the student responses were also collected and evaluated to determine if the Avogadro software’s default optimization parameters are adequate for this application.
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CAS No. : | 10240-08-1 |
Formula : | C11H10O |
M.W : | 158.20 |
SMILES Code : | OC1=C2C=CC=CC2=C(C)C=C1 |
MDL No. : | MFCD00060344 |
Boiling Point : | No data available |
InChI Key : | ZSUDUDXOEGHEJR-UHFFFAOYSA-N |
Pubchem ID : | 82483 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.09 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 50.94 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.87 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.18 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.85 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.83 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.98 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.74 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.44 |
Solubility | 0.0573 mg/ml ; 0.000362 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.28 |
Solubility | 0.0838 mg/ml ; 0.00053 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.87 |
Solubility | 0.0212 mg/ml ; 0.000134 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 |
-5.01 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 |
2.0 |
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 |
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) |
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.