Structure of 10374-51-3
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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.
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CAS No. : | 10374-51-3 |
Formula : | C5H8O3 |
M.W : | 116.12 |
SMILES Code : | O=C1OC(CO)CC1 |
MDL No. : | MFCD00506240 |
InChI Key : | NSISJFFVIMQBRN-UHFFFAOYSA-N |
Pubchem ID : | 98431 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.8 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 26.48 |
TPSA ? Topological Polar Surface Area: Calculated from |
46.53 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.93 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.44 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.32 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.38 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.69 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.1 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.22 |
Solubility | 70.5 mg/ml ; 0.607 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.07 |
Solubility | 98.4 mg/ml ; 0.848 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.16 |
Solubility | 79.8 mg/ml ; 0.687 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) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.32 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 |
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) |
2.03 |
* 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 |
---|---|---|
99% | With hydrogenchloride; dihydrogen peroxide; In methanol; formic acid; | EXAMPLE 56 (+-)-Dihydro-5-Hydroxymethyl-2(3H) -Furanone STR89 To a stirring solution of 19% hydrogen peroxide (35 mL, 0.20 mol) in 85% aqueous formic acid (60 mL) at 50-55 C. was added over a 15 min period a solution of 4-pentenoic acid (15 g, 0.15 mol) in 85% aqueous formic acid (30 mL). The solution was maintained at this temperature for 2 h. Concentration gave an oil which comprised of a mixture of the desired compound and the corresponding formate ester. The oil was then stirred in methanol (50 mL) containing concentrated hydrochloric acid (1 mL) for 3 h. Concentration gave the desired compound as an oil (17.2 g, 99%). 1 H NMR (300 MHz, CDCl3) delta: 4.60 (m, 1H, H-5), 3.89 (dd, 1H, H-6, J=2.7 HZ and 12.6 Hz), 3.63 (dd, 1H, H-6', J=4.5 HZ and 12.3 Hz), 2.6 (m, 2H, H-3), 2.3 (m, 3H, H-4, OH). |
97% | With formic acid; dihydrogen peroxide; at 50℃; for 2.25h; | 4-pentenoic acid (2 g, 20 mmol) was dissolved in formic acid (5 mL), and added dropwise into formic acidsolution (20 mL) containing 35% of hydrogen peroxide (28 mmol) at 50 C over 15 min. At this temperature, the mixturewas stirred for 2 h, and distilled under reduced pressure to give the product 2-keto-5-hydroxymethyl-tetrahydrofuran (2g, yield 97%). |
88% | With dihydrogen peroxide; In tert-butyl alcohol; | EXAMPLE 5 A total of 2 ml of 30% by weight hydrogen peroxide aqueous solution was added dropwise to a stirred mixture of 1.00 g (10 mmol) of 4-pentenoic acid, 25 mg (0.1 mmol) of tungstic acid, and 15 ml of t-butyl alcohol at room temperature, followed by stirring at 70C for 10 hours. As a result, gamma-hydroxymethyl-gamma-butyrolactone was produced in a yield of 88%. |
With N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamineiron(II) bis(triflate); dihydrogen peroxide; In water; acetonitrile; for 0.166667h;Inert atmosphere; Schlenk technique; | General procedure: Epoxidations were performed in 25-mL Schlenk tubes under an inert atmosphere. In a typical run, the tube was charged with 1 equiv of catalyst (typically about 15mg), degassed acetonitrile (20mL) and 200 equiv of substrate. 600 equiv of the oxidant H2O2 (30% w/v in water) were added via syringe over a two-minute period, often resulting in an immediate color change to brown. This color faded to a pale orange for most substrates over a period of 30s. The reaction was allowed to stir for a total of 10min, and then was quenched by pouring the solution into an Erlenmeyer flask containing silica gel and anhydrous magnesium sulfate. The solution was passed through a short column of silica gel, and solvent evaporated under moderate vacuum. As a control, samples of substrates were taken through this workflow without use of catalyst, and analyzed gravimetrically and by 1H NMR. Pure substrate was recovered with no significant mass loss (typical recovery 98%). For other catalyst:substrate:oxidant ratios, the concentration of catalyst was kept constant, and amounts of substrate and oxidant varied. The products were analyzed by 1H NMR in CDCl3 with a relaxation delay of 10s. 1H NMR shifts of the epoxide products matched those reported in the literature [22,36-39]. For oleic acid and ethyl oleate, the shift of the CH3 group of C18 does not change between the starting materials and products. This signal was therefore used as an internal standard to measure conversions by comparing the integrations of the alkene signals relative to the methyl signals [36]. Similarly, epoxide selectivities were calculated from the integrations of the epoxide signals and the methyl signals. For undecylenic acid and methyl undecenoate, a similar approach utilized the methylene group next to the carboxylic acid group as an internal standard. For the epoxidation of 4-pentenoic acid and 5-hexenoic acid, conversions were determined by comparing the integrations of the alkene signals with those of the epoxide and lactone signals. GC-MS data was used to confirm the presence of two major products only, the epoxide and the lactone [38]. Owing to the limit of sensitivity of NMR, in experiments where epoxide or lactone was the only product clearly detected, selectivities of >95% are reported, as low concentrations of other products can not be ruled out. Selected spectra and GC-MS chromatograms are available in the Supplemental information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 7 6.0 g 4,5-epoxypentane carboxylic acid methyl ester is shaken in a mixture of 10 ml ether and 10 ml 2 n HCl for 1 hour. The ether is then separated and the aqueous phase perforated with ether. From the combined dried ethereal phases 3.7 g dihydro-5-hydroxymethyl-(3H)-furanone is obtained after removal of the ether in vacuum. | ||
EXAMPLE 10 6.0 g 4,5-epoxypentane carboxylic acid methyl ester is shaken in a mixture of 10 ml ether and 10 ml 2n HCl for 1 hour. The ether is then separated and the aqueous phase perforated with ether. From the combined dried ethereal phases 3.7 g dihydro-5-hydroxymethyl-(3H)-furanone is obtained after removal of the ether in vacuum. |
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