Structure of ε-Caprolactone
CAS No.: 502-44-3
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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. : | 502-44-3 |
Formula : | C6H10O2 |
M.W : | 114.14 |
SMILES Code : | O=C1OCCCCC1 |
MDL No. : | MFCD00003267 |
InChI Key : | PAPBSGBWRJIAAV-UHFFFAOYSA-N |
Pubchem ID : | 10401 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 8 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.83 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 30.13 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.53 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.01 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.1 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.88 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.87 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.08 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.55 |
Solubility | 31.9 mg/ml ; 0.279 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.11 |
Solubility | 87.8 mg/ml ; 0.769 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.12 |
Solubility | 8.68 mg/ml ; 0.076 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) |
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 |
-6.99 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) |
1.51 |
* 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 |
---|---|---|
95 parts by weight of the <strong>[4224-62-8]6-chlorocaproic acid</strong> were boiled with an aqueous solution of the equivalent amount of sodium hydroxide to obtain 69 parts by weight of epsilon-caprolactone. The 13C-NMR (100 MHz, internal standard CDCl3)of the synthesised epsilon-caprolactone was measured to obtain chemical shfts delta (ppm) as follows: epsilon-caprolactone: 13C-NMR (100 MHz, CDCl3) delta (ppm): 176.23, 69.30, 34.56, 29.35, 28.93, 22.98 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Reaction 1 HGT5000 [0151] The intermediate compound (15Z, 18Z)-6-[ (9Z, 12Z)-octadeca-9, 12-dien-l- yl]tetracosa-15, 18-diene-l, 6-diol identified as compound (2) in Reaction 1 above was prepared as follows. To a lOOmL round bottom flask was added lOg (30mmol) of compound (1) (<strong>[4102-60-7]linoleyl bromide</strong>) and dry THF (20mL) under nitrogen. Magnesium powder (1.1 lg, 45mmol) was added to the stirred reaction solution followed by 2 drops of dibromoethane at room temperature. The reaction mixture was stirred at 50 C for 1 hour, and then diluted with dry THF (40mL). The reaction mixture was stirred another 15 minutes at room temperature. [0152] In a separate 250mL 3-neck flask was taken epsilon-caprolactone (1.44mL, 13.5mmol) in dry THF (20mL) under nitrogen. To the stirred solution was added the Grignard reagent through a cannula at 0 C. The resulting mixture was heated at 85 C for 3 hours. After cooling to room temperature, the reaction mixture was then quenched with NH4CI solution and extracted with dichloromethane (3 x lOOmL). The combined extracts were washed with brine (50mL), dried ( a2S04) and concentrated. The residue was purified twice by silica gel column chromatography (gradient elution from hexane to 3 :2 hexane/EA) to afford compound (2) as an oil. Yield: 5.46g (65%). XH NMR (301 MHz, CDC13) delta: 5.25 - 5.45 (m, 8H), 3.65 (m, 2H), 2.77 (t, J= 6.2 Hz, 4H), 1.95 - 2.1 (m, 8H), 1.2 - 1.70 (m, 50H), 0.88 (t, J= 6.9 Hz, 6H). |