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CAS No. : | 125414-41-7 | MDL No. : | MFCD00270213 |
Formula : | C8H17NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JHBKBRLRYPYBLP-UHFFFAOYSA-N |
M.W : | 191.22 | Pubchem ID : | 10631565 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.88 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 47.41 |
TPSA : | 78.79 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.73 cm/s |
Log Po/w (iLOGP) : | 1.48 |
Log Po/w (XLOGP3) : | -0.37 |
Log Po/w (WLOGP) : | -0.14 |
Log Po/w (MLOGP) : | -0.2 |
Log Po/w (SILICOS-IT) : | -0.32 |
Consensus Log Po/w : | 0.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.4 |
Solubility : | 76.7 mg/ml ; 0.401 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.82 |
Solubility : | 28.8 mg/ml ; 0.151 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.54 |
Solubility : | 54.9 mg/ml ; 0.287 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.23 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | 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 |
---|---|---|
100% | at 20℃; for 16 h; | To a solution of 2-anunopropane-1 ,3-diol (1 0. 0 g, 0.1 mol) in EtOH ( 100 mL) wasadded di-tert-butyl dicarbonate (24.0 g, 0.1 mol). The reaction was stirred at room temperaturefor 16 hrs. The reaction solution was concentrated in vacuo to dryness to give tert-butyl (1,3-dihydroxypropan-2-yl)carbamate (21.0 g, yield: 1 00'percent) as a white solid. |
97% | at 22 - 25℃; for 4 h; | Serinol (2.00 g, 21.96 mmol) and (Boc)20 (4.80 g, 21.96 mmol) was dissolved in 20 mL of dichloromethane. The reaction mixture was stirred for 4 h at 22 to 25 °C. The above mixture was washed with water (25 mL x 2), dried over anhydrous sodium sulfate and concentrated under vacuum toyield tert-butyl (1 ,3-dihydroxypropan-2-yl)carbamate (4.1 g, 97percent yield). |
95% | With hydrogenchloride In 1,4-dioxane; water at 20℃; Cooling with ice | Serinol (10.1 mmol) (manufactured by Aldrich Chem. Co.) was dissolved in water-dioxane (1:1, 20 ml), andthen a dioxane solution (15 ml) of Boc2O (10.8 mmol) was added thereto under ice-cooling, followed by stirring overnightwhile returning to room temperature. The solvent was evaporated under reduced pressure. The residue was washedwith hexane and then dried under reduced pressure to give the titled compound (1847 mg, yield 95percent).The structurewas identified by 1H-NMR.1H-NMR (500 MHz, CD3OD) δ (ppm) = 1.44 (9H, s, Boc), 3.57-3.58 (5H, m, Serinol) |
91% | at 20℃; for 6 h; | 2-amino-1,3-propanediol (5 g) was dissolved in 150 mL of absolute ethanol, A solution of 100 mL of Boc anhydride (12 g) in absolute ethanol was added, Room temperature reaction 6h, Remove the solvent, Recrystallization from n-heptane gave a white solid 3 (9.6 g, 91percent). |
72% | With N-ethyl-N,N-diisopropylamine In methanol for 0.25 h; | Example 2Λ/-Boc-Serinol. Λ/,Λ/-diisopropylethylamine (DIEA; 10.3 ml_, 59 mmol, 1.1 equiv) was added to serinol (4.88 g, 54 mmol, 1 equiv) in 10 ml_ methanol. A solution of di-f-butyl dicarbonate (12.9 g, 59 mmol, 1.1 equiv.) in 5 mL methanol was then added to the original solution. The reaction was exothermic and evolved gas. The reaction appeared to be complete after 15 min. (as determined by TLC analysis in 9:1 CHCI3:CH3OH with ninhydrin stain). The solvent was then removed at reduced pressure, and the crude material was purified by flash chromatography, using CHCI3:CH3OH (first at a 9:1 ratio and then at a 85:15 ratio), to yield 7.18g (72percent yield) of white, flaked crystals. [Rf: 0.35 (5:1 CHCI3:CH3OH); melting point 85-860C; 1H NMR (200 MHz, CDCI3) δ 5.25 (br d, J = 5.6, 1 H, NH), 3.9-3.65 (m, 5H, (-CH2)2CH-), 2.62 (t, J = 5.6, 2H, OH), 1.45 (s, 9H, C(CHa)3)]. EPO <DP n="30"/>Example 3[0107] To prepare the bis-phthalonitrile used in scheme 2, the nitrogen of serinol was Boc-protected, and the serinol was then reacted with 3-nitrophthalonitrile on a multi-gram scale, to give the desired tethered bis-phthalonitrile, in 70percent yield |
49% | With triethylamine In tetrahydrofuran at 0 - 20℃; | 2-Amino-1 ,3-propanediol (5.Og, 54.9mmol) was dissolved in dry THF (175ml) and triethylamine (7.7ml) added. The solution was cooled in an ice-bath and di-fe/f- butylcarbonate (11.98g, 54.9mmol) added in portions over 15mins. The solution was allowed to warm to ambient temperature and stirred for 90mins. The solvent was evaporated and water (250ml) added and the product extracted into ethyl acetate (4 x 125ml). The combined organics were washed with brine, dried over magnesium sulphate, filtered and evaporated. The product was isolated by recrystallization from hot ethyl acetate-petrol (1 :3) to give shiny flakes 5.18g (49percent yield). The structure was confirmed by 1H NMR (300MHz , CDCI3): 1.44 (s, 9H), 3.08-3.17 (m, 1 H), 3.61 - 3.84 (m, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 1.75 h; | Preparation J(2-Hydroxy-1-hvdroxymethyl-ethyl)-carbamic acid tert-butyl esterO H ^OH <n="23"/>2-Amino-1 ,3-propanediol (5.Og, 54.9mmol) was dissolved in dry THF (175ml) and triethylamine (7.7ml) added. The solution was cooled in an ice-bath and di-te/f- butylcarbonate (11.98g, 54.9mmol) added in portions over 15mins. The solution was allowed to warm to ambient temperature and stirred for 90mins. The solvent was evaporated and water (250ml) added and the product extracted into ethyl acetate (4 x 125ml). The combined organics were washed with brine, dried over magnesium sulphate, filtered and evaporated. The product was isolated by recrystallization from hot ethyl acetate-petrol (1 :3) to give shiny flakes 5.18g (49percent yield).The structure was confirmed by 1H NMR (300MHz , CDCI3): 1.44 (s, 9H), 3.08- 3.17 (m, 1 H), 3.61 - 3.84 (m, 4H). |
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