Structure of 87199-15-3
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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.
Synonyms: 3-Hydroxymethylbenzeneboronic acid
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Guo, Sheng ; Wu, Yifan ; Luo, Shao-Xiong Lennon ; Swager, Timothy M. ;
Abstract: Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.
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Keywords: nanoporous organic polymer ; heterogeneous catalyst ; Suzuki−Miyaura coupling reaction ; size-selective reaction ; catalyst processing
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Purchased from AmBeed: 128796-39-4 ; 10365-98-7 ; 98-80-6 ; 556-96-7 ; 171663-13-1 ; 71597-85-8 ; 402-43-7 ; 2042-37-7 ; 22385-77-9 ; 16419-60-6 ; 15862-18-7 ; 87199-15-3 ; 171408-84-7 ; 643-58-3 ; 591-50-4 ; 76911-73-4 ; 398-36-7 ; 14871-92-2 ; 5720-07-0 ; 945976-76-1 ; 366-18-7 ; 2920-38-9 ; 623-00-7 ; 24973-49-7 ; 588-59-0 ; 128796-39-4 ; 5723-93-3 ; 17057-88-4 ; 126485-55-0
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CAS No. : | 87199-15-3 |
Formula : | C7H9BO3 |
M.W : | 151.96 |
SMILES Code : | C1=C(C=CC=C1CO)B(O)O |
Synonyms : |
3-Hydroxymethylbenzeneboronic acid
|
MDL No. : | MFCD01317846 |
InChI Key : | HGTDLKXUWVKLQX-UHFFFAOYSA-N |
Pubchem ID : | 2734662 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 42.4 |
TPSA ? Topological Polar Surface Area: Calculated from |
60.69 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 |
-0.06 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-1.29 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.27 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.91 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.51 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.02 |
Solubility | 14.6 mg/ml ; 0.0964 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.76 |
Solubility | 26.2 mg/ml ; 0.172 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.1 |
Solubility | 12.0 mg/ml ; 0.0793 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 |
No |
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) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.27 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) |
1.58 |
* 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 |
---|---|---|
89% | With C44H32Cl4I2N4P2Pd2; tetrabutylammomium bromide; caesium carbonate; In water; at 100℃; for 12h;Inert atmosphere; | General procedure: A Schlenk tube was charged with the prescribed amount of catalyst, aryl halide (1.0 mmol), 3-(hydroxymethyl)phenylboronicacid (1.5 mmol), TBAB (1.0 mmol), the selected base (3.0 mmol), and water under nitrogen atmosphere. The reaction mixture was heated at 100 C for 12 h. After cooling,the mixture was extracted with CH2Cl2, the solvent was evaporated,and the product was separated by passing through a silica gel column with CH2Cl2/ethyl acetate (5:1) aseluent. The products 2f, 2j, 2l, and 2o were new compounds and were determined by 1H and C13 NMR. Other products were characterized by comparison with data in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.4% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 110℃; for 2h;Inert atmosphere; | To a solution of methyl 6-chloro-3-methyl-pyridine-2- carboxylate (1.0 g, 5.39 mmol) in 1,4-dioxane (17.9 ml) and H20 (2.9 ml) is added (3- (hydroxymethyl)phenyl)boronic acid (0.982 g, 6.47 mmol) followed by K2C03 (1.86 g, 13.47 mmol) and PdCl2(dppf)*CH2Cl2 (131.9 mg, 0.13 mmol). The reaction mixture is purged with argon for 5 minutes and then heated at 110C. After 2 hours, the reaction is cooled to room temperature, diluted with water and extracted with EtOAc. The combined organic layers are dried over magnesium sulfate, filtered, and concentrated. The residue is purified by silica gel flash chromatography using 70% EtOAc in hexane to afford methyl 6-[3-(hydroxymethyl)phenyl]-3-metliyl-pyridine-2-carboxylate (0.713 g, 51.4%). Mass spectrum (m/z): 258.0 (M+l)+. |
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