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CAS No. : | 2774-84-7 | MDL No. : | MFCD00041675 |
Formula : | C11H20O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YUQZOUNRPZBQJK-UHFFFAOYSA-N |
M.W : | 168.28 | Pubchem ID : | 76015 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.82 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 54.31 |
TPSA : | 20.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.62 cm/s |
Log Po/w (iLOGP) : | 3.04 |
Log Po/w (XLOGP3) : | 3.81 |
Log Po/w (WLOGP) : | 2.81 |
Log Po/w (MLOGP) : | 2.99 |
Log Po/w (SILICOS-IT) : | 3.28 |
Consensus Log Po/w : | 3.19 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.76 |
Solubility : | 0.295 mg/ml ; 0.00176 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.93 |
Solubility : | 0.0198 mg/ml ; 0.000118 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.02 |
Solubility : | 0.159 mg/ml ; 0.000946 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 2.96 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
98% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 15h; Inert atmosphere; | |
97% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; | |
97% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | Undec-10-yn-1-ol [3b] Lithium aluminium hydride (0.19 g, 5.0 mmol) was added to dry THF (10 mL) at 0 °C under nitrogen atmosphere. Subsequently, undec-10-ynoic acid (0.46 g, 2.5 mmol) in dry THF (5 mL) was added dropwise over 20 minutes. The mixture was allowed to warm to room temperature, stirred for 2 hours and then quenched with ethyl acetate (5 mL) and water (5 mL). The mixture was filtered over a glass filter. The product was extracted with ethyl acetate (3 x 30 mL) and washed with and water (3 x 30 mL).The combined organic layers were dried with MgSO4, filtered andconcentrated under reduced pressure to yield 20 as pink oil (0.40 g, 2.4 mmol). Yield: 97%. Rf = 0.24 (1 : 10 ethyl acetate : petroleum ether). 1H NMR (500 MHz, CDCl3) δ 3.60 - 3.57 (t, J = 7.1Hz, 2H), 2.19 - 2.13 (td, J = 7.1, 2.6 Hz, 2H), 1.93 (t, J = 2.6Hz, 1H), 1.56 - 1.47 (m, 4H), 1.32 (m, 10H). 13C NMR (126 MHz, CDCl3) δ 84.7, 68.1, 62.8, 32.7, 29.4,29.3, 29.0, 28.7, 28.4, 25.7, 18.3. |
85% | With lithium aluminium tetrahydride In diethyl ether 25 deg C, 24 h, reflux, 3 h; | |
85% | With lithium aluminium tetrahydride In diethyl ether at 40℃; for 3h; | |
84% | With lithium aluminium tetrahydride In diethyl ether for 4h; Heating; | |
63% | With lithium aluminium tetrahydride In diethyl ether at 0℃; for 4h; | |
With lithium aluminium tetrahydride | ||
Multi-step reaction with 2 steps 1: 95.4 percent / conc.H2SO4 / methanol / 4 h / Heating 2: 91.6 percent / LAH / diethyl ether / 2 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: HCl / zuletzt bei Siedetemperatur 2: sodium; butyl alcohol | ||
With lithium aluminium tetrahydride | ||
Multi-step reaction with 2 steps 1: 12 h / 20 °C 2: lithium aluminium tetrahydride / 4 h / 20 °C | ||
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium In tetrahydrofuran; hexane 1.) -70 deg C, 2.) 18 h, RT; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium 1) THF, Hexan, 2) THF, 5 h, room temp.; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; hydroxylamine hydrochloride; ethylamine; copper(l) chloride In tetrahydrofuran; methanol Ambient temperature; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With copper(l) iodide; triethylamine at 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; for 2.5h;Heating / reflux;Product distribution / selectivity; | (Method G) A solution of commercially available 2-[(8-bromooctyl)oxy]tetrahydro-2H-pyran (1.0 g, 3.4 mmol, 1 equiv.) in DMSO (5 ml), was added, slowly, dropwise, at r.t., under N2, to a stirred suspension of lithium acetylide ethylenediamine complex (350 mg, 3.8 mmol, 1.1 equiv.) in DMSO (5 ml). The reaction mixture was stirred at r.t. for 18 h and diluted with n-pentane (50 ml). The organic phase was washed with 1N HCI solution (2x20 ml) and water (2x20 ml), dried (Na2SO4) and evaporated to dryness under reduced pressure. The residue (colourless liquid, 570 mg, yield 70%) was dissolved in 95% EtOH (20 ml) together with p-toluenesulfonic acid (150 mg) and the mixture was heated under reflux for 2.5 h. After being cooled, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with EtOAc/hexane (10%-30% gradient), to give the desired compound as a colourless oil (240 mg, overall yield 48%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: 10-Undecen-1-ol With bromine In dichloromethane at -45 - 20℃; Stage #2: With potassium hydroxide for 5h; Reflux; Inert atmosphere; | |
Multi-step reaction with 2 steps 1: Br2 / CCl4 / 1 h / 0 °C 2: 80 percent / NaNH2, ethylenediamine | ||
Multi-step reaction with 2 steps 1: 100 percent / Br2 / CCl4 / 1 h 2: 81 percent / KOH, PEG-200 / 2 h / Heating |
Multi-step reaction with 3 steps 1: bromine / CCl4 2: potassium / ethanol / 2 h / Heating 3: potassium / ethane-1,2-diol / 5 h / 120 °C | ||
Multi-step reaction with 2 steps 1: 92 percent / bromine / CH2Cl2 / 4 °C 2: 80 percent / KOH, 18-crown-6 / heptane | ||
Multi-step reaction with 2 steps 1: Br2 / CCl4 / 4 h / Ambient temperature 2: Na, anhydrous FeCl3 / liquid ammonia / 6 h | ||
Multi-step reaction with 2 steps 1: 100 percent / bromine / diethyl ether / 0.5 h / -10 - 0 °C 2: 60 percent / NaNH2/liq. NH3 / diethyl ether / 0.5 h / Heating | ||
Multi-step reaction with 2 steps 1: Br2 / CH2Cl2 / 1.) -5 to 0 deg C, 4 h, addition of bromine; 2.) 0 deg C, 4 h 2: 78 percent / sodium amide / tetrahydrofuran; liquid ammonia / 17 h | ||
Multi-step reaction with 2 steps 1: Br2 / -10 - 0 °C 2: 60 percent / NaNH2 / liquid ammonia | ||
Multi-step reaction with 2 steps 1: Br2 2: NaNH2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: p-TsOH*H2O / 2 h / Ambient temperature 2: n-BuLi / tetrahydrofuran; hexane 3: p-TsOH*H2O / methanol / 1 h / Heating 4: 100 percent / pyridine / 3.5 h / Ambient temperature 5: 62 percent / dichloromaleic anhydride / 200 °C 6: 94 percent / 2 M KOH / ethanol / Heating 7: 68 percent / CBr4, PPh3 / CH2Cl2 / Ambient temperature 8: 70 percent / n-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide 9: 98 percent / H2, quinoline / 5percent Pd/CaCO3 / cyclohexane / 750.06 Torr 10: 88 percent / AlI3, cyclohexene / CS2 / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) HMPA. 2.) HMPA 2: H2 / Pd/C / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With quinoline; hydrogen In ethanol | 7.7a 7a. undec-10-en-1-ol A mixture of undec-10-yn-1-ol (0.84 g, 5.0 mmol), quinoline (0.13 ml), lindlar's catalyst (100 mg, 17% w/w) and EtOH (20 ML) was hydrogenated in a Parr apparatus at 50 psi of H2 for 1 h.The mixture was filtered through Celite, and the filtrate was concentrated in vacuo to dryness to give undec-10-en-1-ol (0.86 g, 100%) as a colorless oil, which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) δ 5.78 (1H, m), 4.92 (2H, m), 3.61 (2H, t, J=6.6 Hz), 2.01 (2H, m), 1.53 (3H, m), 1.21-1.40 (12H, m); 13C NMR (75 MHz, CDCl3) δ 139.43, 114.31, 63.24, 34.00, 32.98, 29.74, 29.61, 29.31, 29.11, 25.92. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | To a solution of alkyne J (5 mmol, 1 eq) and 2-chloroquinoline (6.5 mmol, 1.3 eq) in triethylamine (25 mmol, 5 eq) and THF (3 ml) under inert atmosphere of nitrogen are added PdCl2(PPh3)3 (0.25 mmol, 0.05 eq) and CuI (0.5 mmol, 0.1 eq) in this order. The mixture is heated at 70 C. for 3 hours, hydrolyzed and extracted with dichloromethane. The organic phase is then washed with water and then with a 0.1 M HCl solution, dried on MgSO4, and then evaporated under reduced pressure. Purification is carried out on a silica column in a mixture of cyclohexane and ethyl acetate in a proportion of 7:3 and then 6:4. A secondary product resulting from the dimerization of the alkyne compound with itself is obtained with a yield between 10% and 20%.Yield: 87%1H NMR (400 MHz, CDCl3) delta ppm: 1.32 (s, 8H); 1.46 (m, 2H); 1.55 (m, 2H); 1.64 (m, 2H); 2.48 (t, J=7.2 Hz, 2H); 3.62 (t, J=6.8 Hz, 2H); 7.43 (d, J=8.4 Hz, 1H); 7.49 (t, J=7.6 Hz, 1H); 7.68 (t, J=8.0 Hz, 1H); 7.75 (d, J=8.4 Hz, 1H); 8.06 (d, J=8.4 Hz, 2H).13C NMR (50 MHz, CDCl3) delta ppm: 19.4, 25.6, 28.2, 28.8, 28.9, 29.2, 29.3, 32.7, 62.8, 81.1, 92.1, 124.1, 126.6, 126.8, 127.3, 129.0, 129.7, 135.8, 144.0, 147.9MS(EI)-m/z: 295 (M+, 2); 278 (C20H24N1, 6); 264 (C19H22N1, 13); 250 (C18H20N1, 17); 236 (C17H18N1, 34); 222 (C16H16N1, 80); 208 (C15H14N1, 76); 194 (C14H12N1, 54); 180 (C13H10N1, 100); 166 (C12H8N1, 42); 140 (C10H6N1, 38); 128 (C9H6N1, 26).IR cm-1: 617, 637, 694, 721, 754, 787, 829, 871, 953, 1057, 1120, 1141, 1238, 1261, 1277, 1307, 1336, 1373, 1424, 1463, 1500, 1555, 1595, 1617, 2226, 2853, 2925, 3058, 3312. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With silver(I) acetate at 60℃; for 15h; | |
95 %Spectr. | With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) at 25℃; for 3h; | |
Stage #1: pyridine N-oxide; bis(trifluoromethanesulfonyl)amide In dichloromethane at 20℃; for 0.5h; Cooling with ice; Stage #2: undec-10-yn-1-ol With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) at 20℃; | 9 Example 9 Pre-prepared compound A (1.2 equiv., 90.2 mg) was added to a 4 ml reaction flask in turn, and the substrate alkyne 1 h was added.(0.2 mmol, 33.6 mg), PPh3AuNTf2 (2.5%, 3.7 mg), HFIP (0.2 ml), stirred at room temperature for 2.5 hours, charged 20 times equivalent of benzene, heated to 90 ° C, stirred for 18 hours, TLC monitoring After completion of the reaction, flash column chromatography (eluent petroleum ether: ethyl acetate = 10:1) gave a colorless oily liquid.The yield can reach 65%. |
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With palladium on activated charcoal; hydrogen In ethyl acetate at 50℃; for 0.00833333h; Green chemistry; |