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CAS No. : | 5272-36-6 | MDL No. : | MFCD00002913 |
Formula : | C6H12OSi | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZVGCJDPEKKEYES-UHFFFAOYSA-N |
M.W : | 128.24 | Pubchem ID : | 78930 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 38.15 |
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) : | -5.94 cm/s |
Log Po/w (iLOGP) : | 2.1 |
Log Po/w (XLOGP3) : | 1.61 |
Log Po/w (WLOGP) : | 0.94 |
Log Po/w (MLOGP) : | 1.39 |
Log Po/w (SILICOS-IT) : | -0.41 |
Consensus Log Po/w : | 1.13 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.65 |
Solubility : | 2.87 mg/ml ; 0.0224 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.65 |
Solubility : | 2.89 mg/ml ; 0.0226 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.02 |
Solubility : | 12.3 mg/ml ; 0.0957 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.83 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
89% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4 h; Heating / reflux Stage #2: With water; ammonium chloride In tetrahydrofuran |
Example 41; (2E)-3-(Trimethylsilyl)prop-2-en-1-ol; The alcohol produced in Example 40 (1.54 g, 12 mmol, 1 eq) in dry THF (12 mL) was added dropwise, with stirring, to a suspension of LiAlH4 (0.7 g, 18 mmol, 1.5 eq) in THF (15 mL) at room temperature, under argon. The mixture was then refluxed for 4 hours and quenched with sat. NH4.Cl. This was extracted with Et2O (3.x.50 mL) and the combined organic layers were washed with brine, dried over MgSO4 and the solvent removed in vacuo to furnish the product (1.39 g, 10.6 mmol, 89percent yield) as a colourless liquid. 1H NMR (400 MHz, CDCl3) δ 6.19 (1H, m, H-3), 5.93 (1H, dt, J2-3=18.8 Hz, J2-4=1.45 Hz, H-2), 4.18 (2H, dd, J4-3=2.72, J4-2=1.45, H-4), 1.56 (1H, s, H-5), 0.09 (9H, s, H-1); 13C NMR (100 MHz, CDCl3) δ 144.8 (C-3), 129.5 (C-2), 65.5 (C-4), -1.37 (C-5); IR (neat, cm-1) 3331 (b, OH) 1622 (s, CC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sulfuric acid In hexane; ethyl acetate; toluene | EXAMPLE 38 Preparation of (E)-3-Trimethylsilyl-2-Propen-1-Ol 2 g (15.6 mmol) of 3-trimethylsilyl-2-propyn-1-ol in 10 ml of dry ether are added dropwise to an ice-cooled solution of sodium bis(2-methoxyethoxy) aluminum [Red-Al. 3.4M in toluene, (7.3 ml, 25.1 mmol)] in 10 ml of dry ether. The reaction mixture is then further stirred during 2 hours at room temperature and poured into an ice-cooled sulfuric acid (1N) ether mixture. If necessary the pH is adjusted to be slightly basic, the organic phase is then removed and the aqueous phase is further extracted with ether. The combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure. Rapid flash chromatography of the residue on a silica gel column eluted with a 8:2 mixture of hexane and ethyl acetate affords the expected (E)-3-trimethylsilyl-2-propen-1-ol as a colorless liquid (1.8 g, 90percent). |
90% | With sulfuric acid In hexane; ethyl acetate; toluene | EXAMPLE 38 Preparation of (E)-3-Trimethylsilyl-2-Propen-1-Ol 2 g (15.6 mmol) of 3-trimethylsilyl-2-propyn-1-ol in 10 ml of dry ether are added dropwise to an ice-cooled solution of sodium bis(2-methoxyethoxy) aluminum [Red-A1. 3.4M in toluene, (7.3 ml, 25.1 mmol)] in 10 ml of dry ether. The reaction mixture is then further stirred during 21/2 hours at room temperature and poured into an ice-cooled sulfuric acid (1N) ether mixture. If necessary the pH is adjusted to be slightly basic, the organic phase is then removed and the aqueous phase is further extracted with ether. The combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure. Rapid flash chromatography of the residue on a silica gel column eluted with a 8:2 mixture of hexane and ethyl acetate affords the expected (E)-3-trimethylsilyl-2-propen-1-ol as a colorless liquid (1.8 g, 90percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With Amberlyst® 15 In methanol at 0 - 40℃; for 8 h; Inert atmosphere | In a flask containing methanol (4.0 mL) and Amberlyst-15 (0.025 g) under N2, compound 5 (0.250 g,1.17 mmol) was added dropwise at 0 °C. The mixture was stirred at 40 °C for 8 hr, then the resin was filtered, and washed with ethyl acetate (10 mL). A 10 percent aqueous solution of HCl (10 mL) was added and the organic layer was extracted with ethyl acetate (3 × 10 mL), and dried over Na2SO4. After concentration, the residue was purified by column chromatography (hexane/ethyl acetate 9:1) to afford compound 6 in 96 percent yield (0.143 g, 1.12 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333 h; Stage #2: at -78 - 20℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 16 h; |
Example 40; 3-(Trimethylsilyl)prop-2-yn-1-ol; n-BuLi (27.3 mL, 44 mmol, 2.2 eq.) was added dropwise to a stirred solution of 2-propyn-1-ol (1.16 mL, 20 mmol, 1 eq.) in THF (60 mL) at -78° C. under argon. After 20 minutes, trimethylsilyl chloride (52 mL, 60 mmol, 2 eq.) was added dropwise and the mixture allowed to warm to room temperature. 2M HCl (40 mL) was added at 0° C., and the reaction mixture was stirred at room temperature for 16 hours. The organic layer was separated and the aqueous layer extracted with Et2O (3.x.60 mL), the combined organics were washed with brine, dried over MgSO4 and the solvent removed in vacuo. Column chromatography (cyclohexane followed by Et2O), distillation using Kugelrohr apparatus (95-100° C., 11 mbar) and further column chromatography (hexane:Et2O 60:40) furnished the product (0.96g, 7.5 mmol, 37percent yield) as a colourless liquid. Rf=0.55 (cyclohexane:Et2O 1:1); 1H NMR (400 MHz, CDCl3) δ 4.28 (2H, s, H-4), 1.64 (1H, s, H-5), 0.18 (9H, s, H-1); 13C NMR (100 MHz, CDCl3) δ 104.10 (C-3), 91.03 (C-2), 51.99 (C-4), 0.00 (C-1); IR (neat, cm-1) 3426 (b, OH), 2253 (s, C.ident.C); MS (lit.- Bunce, R.; Hertzler, D., J. Org. Chem 1986, 51, 3451-3453: m/z 128.0695). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With sec.-butyllithium In tetrahydrofuran; hexane at -45 - 20℃; for 6 h; Inert atmosphere | A cold (-50 °C) solution of ether 1 (10.2 g, 0.08 mol) in anhydrous THF (50 mL) was added to a solution of BusLi (obtained from BusCl (7.4 g, 0.08 mol) and fine dispersion of lithium (1.39 g, 0.2 mol)) in anhydrous hexane (50 mL) cooled to -60 °C over 10 min. The reaction mixture was stirred under an inert atmosphere for 1 h at -45 °C, then the temperature was gradually increased to ambient over 5 h. The reaction mixture was quenched with 10percent aqueous HCl and extracted with diethyl ether. The extract was dried with MgSO4, the solvent was evaporated. The residue was distilled in vacuo to obtain 3-trimethyl-silylprop-2-yn-1-ol (4) (4.6 g, 45percent), b.p. 74—75 °C (11 Torr). IR (microlayer), n/cm-1: 2174 (Si—CC—), 1240 (CH3—Si). 1H NMR (CDCl3), d: 4.28 (s, 2 H, CH2O); 0.17 (s, 9 H, (CH3)3SiC). 13 NMR (CDCl3), d: 104.15 (Si—CC); 89.82 (Si—CC); 51.58 (CH2O); -0.29 ((CH3)3Si—C); -0.11 (OSi(CH3)3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bromine; triphenylphosphine In dichloromethane at 0℃; for 1 h; Inert atmosphere | To a solution of triphenylphosphine (9.735 g, 37.11 mmol) in dry dichloromethane (46.0 mL) under N2, bromine (5.438 g, 34.03 mmol) was added at 0 °C. After 30 min, when the solution color changed from orange to white, compound 6 (3.960 g, 30.93 mmol) was slowly added. The mixture was stirred for 1 h, and then it was washed with water (3 × 30 mL) and a 10 percent aqueous solution of HCl (2 × 20 mL). The aqueous layer was extracted with ethyl acetate (3 × 20 mL), and then the combined organic layers was dried over Na2SO4 and concentrated in vacuum. The residue was purified by column chromatography, using hexane as eluent, to afford compound 7 in 70 percent yield (4.125 g, 21.6 mmol). |