Structure of Tridecane-1,13-diol
CAS No.: 13362-52-2
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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. : | 13362-52-2 |
Formula : | C13H28O2 |
M.W : | 216.36 |
SMILES Code : | OCCCCCCCCCCCCCO |
MDL No. : | MFCD00482067 |
InChI Key : | HCEPYODGJFPWOI-UHFFFAOYSA-N |
Pubchem ID : | 11063855 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 12 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 66.93 |
TPSA ? Topological Polar Surface Area: Calculated from |
40.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.31 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.08 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.26 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.76 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.78 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.44 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.96 |
Solubility | 0.237 mg/ml ; 0.0011 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.63 |
Solubility | 0.00502 mg/ml ; 0.0000232 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.0 |
Solubility | 0.0217 mg/ml ; 0.0001 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) |
Yes |
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 |
-4.72 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
1.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
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<3.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.0 |
* 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 hydrogen bromide; In water; toluene; for 48h;Reflux; | Place a 1,13-tridecanol (21.6 g, 100 mmol) in a 500 mL round bottom flask,Toluene (analytical grade, 250 mL) and a 48 wt% aqueous solution of hydrobromic acid (13.5 mL, 120 mmol), the reaction mixture was stirred at reflux for 48 h.TLC detection until the material disappears. After the reaction solution was cooled to room temperature, it was diluted with n-hexane.The obtained organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and dried over anhydrous sodium sulfate. After the solvent was distilled off,13-bromo-1-tridecanol (27.5 g, 99%) was obtained.The obtained product 13-bromo-1-tridecanol has high purity and can be directly used in the next reaction. |
99% | With hydrogen bromide; In water; toluene; for 48h;Reflux; | In a 500 mL round-bottom flask, place 1,13-tridecanediol (21.6 g, 100 mmol), toluene (analytical grade, 250 mL) and 48 wt% aqueous hydrobromic acid solution (13.5 mL, 120 mmol),The reaction mixture was stirred at reflux for 48h. TLC detection until the raw material disappears. After the reaction solution was cooled to room temperature, it was diluted with n-hexane.After washing the obtained organic phase with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and after evaporating the solvent,13-Bromo-1-tridecyl alcohol (27.5 g, 99%) was obtained.The resulting product 13-bromo-1-tridecyl alcohol has a higher purity and can be directly used in the next reaction |
98% | With hydrogen bromide; In water; toluene; for 22h;Dean-Stark; Reflux; | To a suspension of 40 (5.0 g, 23.1 mmol) in toluene (130 mL) was added HBr (48% aq., 2.9 mL, 25.4 mmol). The mixture was refluxed for 17 hr, while trapping the water by using a Dean-Stark trap. An aliquot was taken and evaporated to dryness. NMR showed it still contained 40. Additional HBr (48% aq., 8.1 mL, 71 mmol) and toluene (60 mL) were added and continued to reflux for additional 5 hr, trapping the water by using a Dean-Stark trap. Stop the reaction. The reaction mixture was evaporated to dryness to leave the crude product 41 (6.3 g, 98%) as off-white solid. 'H NMR (500 MHz, Chloroform-ri) d 3.64 (t, J= 6.6 Hz, 2H), 3.41 (t, .7= 6.9 Hz, 2H), 1.85 (dt, J= 14.5, 7.0 Hz, 2H), 1.66 - 1.49 (m, 2H), 1.49 - 1.17 (m, 19H). |
67% | With hydrogen bromide; In cyclohexane; water; for 3h;Reflux; Inert atmosphere; | Aqueous HBr (48%, 16 mL) was added under vigorous stirring to diol 11 (2.644 g, 12.22 mmol, 1.00 equiv) suspended in cyclohexane (32 mL). The mixture was stirred and heated to reflux for 3 h, and the aqueous phase was separated after cooling to r.t. and extracted with EtOAc (3 30 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The remainder was purified by column chromatography (cyclohexane/EtOAc, 3:1) to afford the title compound. Yield: 2.284 g (8.179 mmol, 67%); colourless solid; mp 54-55 C (lit.6b mp 56-57 C); Rf = 0.51 (cyclohexane/EtOAc, 3:1). IR (ATR): 3428, 2917, 2851, 1468, 1355, 1327, 1253, 1205, 1058, 1049, 1025, 1010, 995, 969, 722, 645, 604, 570 cm-1. 1H NMR (CDCl3, 500 MHz): δ = 3.64 (dt, J = 5.5, 6.5 Hz, 2 H, 1-H), 3.41 (t, J = 7.0 Hz, 2 H, 13-H), 1.85 (quin, J = 7.0 Hz, 2 H, 12-H), 1.57 (quin, J = 6.5 Hz, 2 H, 2-H), 1.46-1.24 (m, 18 H, 3-H to 11-H), 1.19 (t, J = 5.5 Hz, 1H, OH). 13C NMR (CDCl3, 125 MHz): δ = 63.3, 34.3, 32.98, 32.96, 29.74, 29.70, 29.67, 29.57, 28.92, 28.33, 25.9. |
52% | With hydrogen bromide; In water; toluene; at 0℃; for 18h;Inert atmosphere; Reflux; | To a solution of 43 (7.2 g, 33 mmol) in toluene (105 mL) was added48% aq HBr (4.5 mL, 40 mmol) at 0 C. After stirring for 18 h underreflux conditions, the completion of the reaction was confirmed by TLC(1:1 n-hexane/EtOAc). The reaction mixture was diluted with EtOAcand washed with washed with 1m aq NaOH and brine. The organiclayer was subsequently dried over Na2SO4, filtered, and concentrated.The resulting residue was purified by silica gel column chromatography(4:1 n-hexane/EtOAc) to give 44 (4.9 g, 52%) as white powder. 1H NMR(500 MHz, CDCl3) δ 3.64 (near d, 2H, CH2OH), 3.41 (t, 2H,Jvic=7.0 Hz, CH2Br), 1.89-1.82 (m, 2H, CH2CH2Br), 1.60-1.54 (m,2H, CH2CH2OH), 1.42 (near t, 2H, CH2CH2CH2Br), 1.36-1.27 (m, 17H,-CH2-, OH); 13C NMR (125 MHz, CDCl3) δ 63.1, 34.1, 32.9, 32.8, 29.6,29.6, 29.6, 29.5, 29.4, 28.8, 28.3, 25.8. HRMS (ESI) m/z: found [M+Na]+ 301.1136, C13H27OBr calcd for [M+Na]+ 301.1137. |