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CAS No. : | 32159-21-0 | MDL No. : | MFCD00037352 |
Formula : | C13H13NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VHSFUGXCSGOKJX-JTQLQIEISA-N |
M.W : | 263.25 | Pubchem ID : | 637648 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.31 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 68.59 |
TPSA : | 83.91 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) : | -7.12 cm/s |
Log Po/w (iLOGP) : | 1.58 |
Log Po/w (XLOGP3) : | 1.1 |
Log Po/w (WLOGP) : | 0.87 |
Log Po/w (MLOGP) : | 0.41 |
Log Po/w (SILICOS-IT) : | 0.73 |
Consensus Log Po/w : | 0.94 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.07 |
Solubility : | 2.25 mg/ml ; 0.00853 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.45 |
Solubility : | 0.924 mg/ml ; 0.00351 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.97 |
Solubility : | 2.81 mg/ml ; 0.0107 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.71 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
67% | Stage #1: With sulfuric acid In dichloromethane at 20℃; Cooling with ice Stage #2: With sodium carbonate In dichloromethane; water |
Reference Example 1; (2S,5S)-1-Benzyl 2-tert-butyl 5-hydroxypiperidine-1,2-dicarboxylate (A)Step 1: (S)-1-Benzyl 2-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate 100 g of (S)-1-(benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid was dissolved in dehydrated dichloromethane (2 L), and under ice cooling, concentrated sulfuric acid (10 mL) and 213 g of isobutene were added, followed by stirring overnight at +20° C. or less. The reaction mixture was added to cold aqueous sodium carbonate solution while paying attention to effervescence, followed by liquid separation of the organic phase, washing with saturated brine and drying over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=7/3), and crystallized with hexane/ethyl acetate to afford 80 g of the title compound as a colorless crystalline powder (yield 67percent). Enantiomeric excess: 99.9percent ee or more (CHIRALPAK AD-H, 4.6.x.150 mm, UV 210 nm, hexane/ethanol=2/1, flow rate 1 mL/min., retention time 4.2 min.).[α]20D -43.3° (c 0.52 in CHCl3), according to Non-Patent Document 4 -41.81° (c 6.71, CHCl3); 1H NMR (400 MHz, CDCl3, δ): 1.39 (s, 9H), 2.04 (m, 1H), 2.32 (m, 1H), 2.51 (ddd, J=17.6, 9.5, 3.2 Hz, 1H), 2.62 (ddd, J=176, 10.5, 9.5 Hz, 1H), 4.55 (dd, J=9.5, 2.7 Hz, 1H), 5.25 J=12.2 Hz, 1H), 5.30 (d, J=12.2 Hz, 1H), 7.26-7.41 (m, 5H); |
67% | With sulfuric acid In dichloromethane at 20℃; Cooling with ice | 100 g of (S)-1-(benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid was dissolved in dehydrated dichloromethane (2 L), and under ice cooling, concentrated sulfuric acid (10 mL) and 213 g of isobutene were added, followed by stirring overnight at +20°C or less. The reaction mixture was added to cold aqueous sodium carbonate solution while paying attention to effervescence, followed by liquid separation of the organic phase, washing with saturated brine and drying over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=7/3), and crystallized with hexane/ethyl acetate to afford 80 g of the title compound as a colorless crystalline powder (yield 67percent). Enantiomeric excess: 99.9percent ee or more (CHIRALPAK AD-H, 4.6 x 150 mm, UV 210 nm, hexane/ethanol=2/1, flow rate 1 mL/min., retention time 4.2 min.). [α]20D-43.3°(c 0.52 in CHCl3), according to Non-Patent Document 4 -41.8°(c 6.71, CHCl3); 1H NMR (400 MHz, CDCl3, δ): 1.39 (s, 9H), 2.04 (m, 1H), 2.32 (m, 1H), 2.51 (ddd, J = 17.6, 9.5, 3.2 Hz, 1H), 2.62 (ddd, J = 17.6, 10.5, 9.5 Hz, 1H), 4.55 (dd, J = 9.5, 2.7 Hz, 1H), 5.25 (d, J = 12.2 Hz, 1H), 5.30 (d, J = 12.2 Hz, 1H), 7.26-7.41 (m, 5H); MS m/z: 320 (M+1). |
67% | With sulfuric acid In dichloromethane at 20℃; Cooling with ice | Step 1: (S)-1-Benzyl 2-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate [0239] (S)-1-(Benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid (100 g) was dissolved in dehydrated methylene chloride (2 L), and under ice cooling, concentrated sulfuric acid (10 mL) and isobutene (213 g) were added, followed by stirring overnight at +20 °C or less. The reaction mixture was added to cold aqueous sodium carbonate solution while paying attention to effervescence, followed by liquid separation of the organic phase, washing with saturated brine and drying over anhydrous magnesium sulfate, then the solvent was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate = 7/3), and crystallized with hexane/ethyl acetate to afford 80 g of the title compound as a colorless crystalline powder (yield 67percent). Enantiomeric excess 99.9percent ee or more (CHIRALPAK AD-H, 4.6 x 150 mm, UV 210 nm, hexane/ethanol = 2/1, flow rate 1 mL/min., retention time 4.2 min.). [α]20D -43.3° (c 0.52 in CHCl3), according to Non-Patent Document [Journal of Medicinal Chemistry 1991, 34(3), 956-968. Dolence, EK.; Lin, CE.; Miller, MJ.; Payne, SM. "Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine"] -41.8° (c 6.71, CHCl3); 1H NMR (400 MHz, CDCl3) δ 1.39 (s, 9H), 2.04 (m, 1H), 2.32 (m, 1H), 2.51 (ddd, J = 17.6, 9.5, 3.2 Hz, 1H), 2.62 (ddd, J = 17.6, 10.5, 9.5 Hz, 1H), 4.55 (dd, J = 9.5, 2.7 Hz, 1H), 5.25 (d, J = 12.2 Hz, 1H), 5.30 (d, J = 12.2 Hz, 1H), 7.26-7.41 (m, 5H); MS m/z 320 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With perchloric acid In water at 20℃; for 16 h; | 70percent Aqueous perchloric acid (1.65ml, ca. 0.065mol) was dropwised to a suspension of compound11int-BuOAc (200ml) at room temperature, and the resulting mixture was stirred for 16h. Saturated aqueous sodium bicarbonate (300ml) was added to the solution gradually, and most of thet-BuOAc in the mixture was removed in vacuo. The residue was extracted with chloroform, and the organic layer was washed with brine. After drying over magnesium sulfate, the mixture was filtered, and the solvent was removed in vacuo to give the colorless oil (13.9g, 79percent yield);1H NMR (400MHz, CDCl3)δ: 1.39 (9H, s), 2.01–2.08 (1H, m), 2.27–2.36 (1H, m), 2.45–2.53 (1H, m), 2.59–2.68 (1H, m), 4.55 (1H, dd,J=9.4, 2.6Hz), 5.25 (1H, d,J=12.4Hz), 5.30 (1H, d,J=12.2Hz), 7.31–7.41 (5H, m); ESI/MS:m/z=342 (M+Na). |
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