Structure of 4122-56-9
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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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CAS No. : | 4122-56-9 |
Formula : | C9H8O3 |
M.W : | 164.16 |
SMILES Code : | O=C(OC)C1=CC=CC=C1C=O |
MDL No. : | MFCD00204231 |
InChI Key : | YRMODRRGEUGHTF-UHFFFAOYSA-N |
Pubchem ID : | 243003 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.11 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 43.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.37 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.72 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.47 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.29 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.28 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.85 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.52 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.96 |
Solubility | 1.82 mg/ml ; 0.0111 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.99 |
Solubility | 1.69 mg/ml ; 0.0103 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.41 |
Solubility | 0.634 mg/ml ; 0.00386 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 |
-6.26 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) |
1.28 |
* 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 |
---|---|---|
20% | In methanol; at 20℃; for 24h; | A mixture of commercially available 2-formylbenzoic acid methyl ester (100 mg, 0.61 mmol) and <strong>[57497-39-9]N-(tert-butyl)hydroxylamine hydrochloride</strong> (109 mg, 0.732 mmol) in methanol (5 mL) was stirred at ambient temperature for 24 h. The mixture was then concentrated in vacuo and the crude product was dissolved in ethyl acetate (15 ml) and extracted with water (2*20 ml). After the combined organic layers were dried over Na2SO4 and concentrated in vacuo, chromatography on silica gel provided compound 1 (10 mg, 20percent). MS: m/z 236 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid; In toluene; | EXAMPLE 25 Preparation of methyl o-[N-(1-carbamoyl-1,2-dimethylpropyl)formimidoyl]benzoate STR77 A mixture containing 5.0 g methyl 2-formylbenzoate [C. Brown and M. V. Sargent, J. Chem. Soc. (C), 1818 (1969)] and 4.0 g <strong>[40963-14-2]2-amino-2,3-dimethylbutyramide</strong> and 50 mg p-toluenesulfonic acid in 100 mL toluene is heated under reflux under a Dean-Stark water separator for three hours. The mixture is filtered and concentrated in vacuo. The residue crystallizes on standing and is recrystallized from etherhexane to give analytically pure methyl o-[N-(1-carbamoyl-1,2-dimethylpropyl)formimidoyl]benzoate, mp 79-80.5 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With Tetrakis(dimethylamino)ethylen; In tetrahydrofuran;Inert atmosphere; | General procedure: The appropriate substituted benzylic chloride 2a-o (1 mmol, 1equiv) in anhyd THF (15 mL) was added to methyl 2-formylbenzoate(1a; 328 mg, 2 mmol, 2 equiv) under nitrogen in a twoneckedflask. TDAE (200 mg, 1 equiv) was added dropwise, andthe solution was cooled to -20 C, maintained at this temperaturefor 1 h, and then kept at rt for 3 h. The solution was thenextracted with EtOAc (3 × 20 mL) and the extracts were washedwith brine (3 × 20 mL), dried (MgSO4), and concentrated. Thecrude product was purified by chromatography [silica gel,CH2Cl2-PE (1:1)] and recrystallized from EtOH. |
A281507 [4376-18-5]
2-(Methoxycarbonyl)benzoic acid
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A281507 [4376-18-5]
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