Structure of 406913-93-7
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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. : | 406913-93-7 |
Formula : | C5H10O3 |
M.W : | 118.13 |
SMILES Code : | OC[C@@H]1OCCOC1 |
MDL No. : | MFCD16652371 |
InChI Key : | CMEPUAROFJSGJN-YFKPBYRVSA-N |
Pubchem ID : | 44429359 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 27.37 |
TPSA ? Topological Polar Surface Area: Calculated from |
38.69 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.34 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.91 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.61 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.04 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.75 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.09 |
Log S (ESOL):? ESOL: Topological method implemented from |
0.07 |
Solubility | 138.0 mg/ml ; 1.17 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
0.58 |
Solubility | 450.0 mg/ml ; 3.81 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.02 |
Solubility | 113.0 mg/ml ; 0.959 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 |
-7.67 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) |
2.75 |
* 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 palladium 10% on activated carbon; hydrogen In ethanol for 18 h; | To a so[ution of Intermediate 83 (1 .25 g, 4.74 mmo[) in ethano[ (20 mL) was added pa[[adium, 10 percent on carbon (192 mg) and the reaction mixture stirred under an atmosphere of hydrogen for 18 h. The reaction mixture was fi[tered through a p[ugof Ce[ite®, washing with EtOAc, and concentrated under reduced pressure toafford 630 mg (89percent yie[d) of the tit[e compound as pa[e ye[[ow oi[.1H NMR (500 MHz, Ch[oroform-d): 6 [ppm] 3.85 - 3.67 (m, 5H), 3.66 - 3.57 (m, 2H),3.55 (dd, J = 11.7, 5.9 Hz, 1H), 3.46 (dd, J = 11.1, 10.0 Hz, 1H), 1.75 (5, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20.8% | With sodium hydroxide In tetrahydrofuran; water at 90℃; for 24 h; | 2J (11.1 g, 81.3 mmol) was dissolved in 50 mL of THF. Sodium hydroxide (16.3 g, 406 mmol) in 50 mL of water was added and the reaction was heated in a 90 0C oil bath for one day. Despite the TLC showing the reaction to be only half completed the product was extracted from the aqueous layer with ethyl acetate/THF, dichloromethane, n-butanol. The first two extractions contained product and the starting material, which was later purified by flash <n="157"/>column (ethyl acetate/hexane 30/70). The latter extractions contained pure (S)-(1, 4-dioxan-2- yl)methanol (2K, 1.98 g, 20.8 percent yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.47 (t, 7=9.98 Hz, 1 H) 3.51 - 3.67 (m, 3 H) 3.67 - 3.87 (m, 5 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With sodium hydroxide In water at 20 - 90℃; for 5 h; | The product from step 1 (16.06 g, 92.81 mmol) and 1M NaOH (185 mL, 185 mmol) were mixed and the biphasic mixture stirred at RT. After 2.5 h the reaction mixture was heated to 90° C. degrees for 2.5 h then allowed to cool to RT and evaporated. The remaining slurry was washed with DCM/MeOH (95:5) three times, filtered and the filtrate was evaporated. The remaining 9.5 g of oil was purified by SiO2 chromatography (400 g SiO2) eluting with a MeOH/DCM gradient (0-4percent MeOH over 40 min) to afford a 30percent yield of [1,4]dioxan-2-yl-methanol (114a). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23 g | Stage #1: With boron trifluoride diethyl etherate In toluene at 30 - 38℃; for 0.333333 h; Stage #2: With sodium hydroxide In water; toluene at 16 - 20℃; for 1 h; |
A mixture of (R)-2-(chloromethyl)oxirane (55, 109 mL, 1.62 mol) and BF3.OEt2 (3.4 mL, 0.027 mol) in toluene (200 mL) was heated to an internal temperature of 30° C. and 2-choloroethanol (49 g, 0.53 mol) was added dropwise at a rate sufficient to main the reaction temperature at 36-38° C. The resulting mixture was aged at 36° C. for 20 min. The mixture was cooled to 16° C. and aqueous NaOH (250 mL, 23percent) was added with vigorous stirring over 1 h, maintaining the reaction temperature below 20° C. The mixture was aged for 1 h at rt. The two layers were separated, and the aqueous phase was extracted with toluene (130 mL). The combined organic layers were washed with water (100 mL), the resulting organic layer was distilled to low volume, monitoring the distillate for loss of product to give the final intermediate 56 (23 g).1H-NMR: (CDCl3): δ 3.33-3.84 (m, 9H). |
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