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CAS No. : | 3697-68-5 | MDL No. : | MFCD09759206 |
Formula : | C7H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PAILVKQSHRJIPE-UHFFFAOYSA-N |
M.W : | 144.17 | Pubchem ID : | 12450336 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.86 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 35.84 |
TPSA : | 46.53 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) : | 1.96 |
Log Po/w (XLOGP3) : | 0.08 |
Log Po/w (WLOGP) : | 0.26 |
Log Po/w (MLOGP) : | 0.35 |
Log Po/w (SILICOS-IT) : | 1.09 |
Consensus Log Po/w : | 0.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.52 |
Solubility : | 43.5 mg/ml ; 0.302 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.61 |
Solubility : | 35.3 mg/ml ; 0.245 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.99 |
Solubility : | 14.9 mg/ml ; 0.103 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.71 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | 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 |
---|---|---|
91% | With lithium tri(t-butoxy)aluminum hydride In tetrahydrofuran at 23 - 65℃; for 24 h; | Example 64 Preparation of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (70.90 mL, 70.90 mmol) was added to a stirred solution of diethyl cyclopropane-1,1'-dicarboxylate (6 g, 32.20 mmol) in tetrahydrofuran (129 mL) at 23° C. The resulting solution was heated to 65° C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10percent solution of sodium bisulfate (275 mL) and extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a pale yellow oil (4.60, 91percent): 1H NMR (300 MHz, CDCl3) δ 4.16 (q, J=7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J=7, 4 Hz, 2H). |
91% | With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 65℃; for 24 h; | A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (70.90 mL, 70.90 mmol) was added to a stirred solution of diethyl cyclopropane-1,1′-dicarboxylate (6 g, 32.20 mmol) in tetrahydrofuran (129 mL) at 23° C. The resulting solution was heated to 65° C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10percent solution of sodium bisulfate (275 mL) and extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a pale yellow oil (4.60, 91percent): 1H NMR (300 MHz, CDCl3) δ 4.16 (q, J=7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J=7, 4 Hz, 2H). |
91% | With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 65℃; for 24 h; | Example 64 Preparation of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (70.90 mL, 70.90 mmol) was added to a stirred solution of diethyl cyclopropane-1,1'-dicarboxylate (6 g, 32.20 mmol) in tetrahydrofuran (129 mL) at 23° C. The resulting solution was heated to 65° C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10percent solution of sodium bisulfate (275 mL) and extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a pale yellow oil (4.60, 91percent): 1H NMR (300 MHz, CDCl3) δ 4.16 (q, J=7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J=7, 4 Hz, 2H). |
91% | With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 23 - 65℃; for 24 h; | Example 64 Preparation of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (70.90 mL, 70.90 mmol) was added to a stirred solution of diethyl cyclopropane-1,1'-dicarboxylate (6 g, 32.20 mmol) in tetrahydrofuran (129 mL) at 23° C. The resulting solution was heated to 65° C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10percent solution of sodium bisulfate (275 mL) and extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a pale yellow oil (4.60, 91percent): 1H NMR (300 MHz, CDCl3) δ 4.16 (q, J=7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J=7, 4 Hz, 2H). |
88% | With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 65℃; for 24 h; | Preparation of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate-A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (12 mL, 12 mmol, 2.2 equiv) was added to a stirred solution of diethyl cyclopropane-1,1'-dicarboxylate (1.0 mL, 5.7 mmol, 1.0 equiv) in tetrahydrofuran (19 mL) at 23° C. The resulting solution was heated to 65° C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10percent solution of sodium bisulfate (100 mL) and extracted with ethyl acetate (4*50 mL). |
85% | Stage #1: With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran for 22 h; Stage #2: With hydrogenchloride In tetrahydrofuran; dichloromethane; water |
Synthesis of 1-Hydroxymethyl-cyclopropanecarboxylic acid ethyl ester A solution of lithium aluminum-tri-tert-butoxyhydride 1.0M in THF (28.5 mL, 28.5 mmol) is added to a solution of diethyl 1,1-cyclopropanedicarboxylate (2.0 mL, 11.4 mmol) in anhydrous THF (85.0 mL). After stirring the reaction mixture for 4 h, 10 mL of lithium aluminum-tri-tert-butoxyhydride 1.0M solution in THF is added and the solution is stirred for 18 h. The reaction mixture is diluted with DCM, washed with 1N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine. After drying the organic phase over anhydrous Na2SO4, removal of the solvent under reduced pressure affords 1.60 g of 1-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester that is used in the next step without further purification. Yield: 85percent. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.88 (2H, q, J=4.1 Hz), 1.21-1.33 (5H, m), 2.59 (1H, t, J=6.9 Hz), 3.63 (2H, d, J=7.2 Hz), 4.17 (2H, q, J=7.1 Hz). |
79% | With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 18 h; | To a stirred solution of diethyl cyclopropane-1, 1-dicarboxylate (2.13 g, 11.4 mmol) in THF (80 mL) at RT, lithium aluminum tri-tert-butoxyhydride (38.76 mL, 38.76 mmol, 1.0 M solution in THF) was added slowly. After the addition was completed, the reaction mixture was stirred at RT for 18 hours. The reaction mixture was diluted with ethyl acetate (100 mL), washed with IN aq HCI (20 mL), water (20 mL), 5percent aq. NaHC03 (25 mL), brine (20 mL), dried over anhydrous Na2S04, filtered and concentrated to afford the title compound (1.3 g, 79percent, yellow oil). *H NMR (400 MHz, CDCI3) : δ = 4.20- 4.13(m, 2H), 3.62 (m, 2H), 2.61 (m, 1H), 1.29-1.24 (m, 5H), 0.88-0.85 (m, 2H) ppm. |
55.5% | With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran for 2 h; Inert atmosphere; Reflux | Preparation of intermediate 5A:1 -(hydro xymethyl)cyclopropanecarboxylic acid ethyl esterCyclopropane- 1,1-dicarboxylic acid diethyl ester (0.88 mL, 5 mmol) was dissolved in 10 mL of THE Under nitrogen protection and at room temperature, THF solution of LiAl(0-t-Bu)3H (1.1 M, 10 mL, 11 mmol) was added dropwise. The reaction solution was heated to reflux for 2 hours and it was terminated by adding saturated aqueous solution of ammonium chloride. A great amount of precipitate was produced which was filtered. The organic phase was collected, dried, evaporated, and the resulting residue purified with a silica gel column (n-hexane: ethyl acetate = 10: 1) to give 400 mg of colorless liquid 5A. Yield: 55.5percent. MS (ESI, m/z): [M+H]+: 167.1; 1H-NMR(300MHz, CDC13) δ: 4.14 (q, 2H, J = 7.2 Hz), 3.54 (s, 2H), 1.38 (t, 3H, J= 7.2 Hz), 1.01-1.23 (m, 4H). |
12.9% | With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran for 3 h; Reflux | Example 91 2"-amino-6'-(5-chloropyrid-3-yl)-l"-methyldispiro[cyclopropane-l,3'-chroman-4',4"- imidazol]-5'(l'H)-oneStep A: A mixture of diethyl cyclopropane-l,l-dicarboxylate (14.1 mL, 80.6 mmol) and lithium tri-tert- butoxyaluminohydride (201.4 mL, 201.4 mmol) was heated to reflux in THF for 3 hours. The mixture was cooled down and partitioned between water and EtOAc. The organics were washed with water, brine and dried with Na2S04. This was concentrated down and then purified on a column using 10 to 50percent EtOAc:hexanes to give ethyl l-(hydroxymethyl)cyclopropanecarboxylate (1.5 g, 10.4 mmol, 12.9percent) as an 12.9percent) as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: With triethylamine; isobutyl chloroformate In tetrahydrofuran at -10 - 0℃; for 1 h; Stage #2: With sodium tetrahydroborate; water In tetrahydrofuran at 0℃; for 1 h; |
To a stirring solution of compound 71 (1 .0 g, 6.32 mmol) and triethylamine (0.97 ml, 7.59 mmol) in THF (18 ml) at -10 °C, was added isobutyl chloroformate (0.90 ml, 6.96 mmol) dropwise. Then the reaction mixture was stirred 1 h at 0°C, the insoluble material was filtered off, and the filtrate was directly used later. To an ice-cooling solution of NaBH4 (0.71 g, 18.97 mmol) in THF (10 ml) and water (2.5 ml), was added the filtrate obtained above dropwise. After the reaction mixture was allowed to stirred at 0°C for 1 h, then reaction mixture was poured into 10percent of aqueous solution HOAc, the aqueous phase was extracted with EtOAc (30 ml x 3), and the combined organic phase was washed with brine, dried over Na2S04, filtered and concentrated to afford crude product, which was purified by silica gel column chromatography (Petroleum ether: ethyl acetate = 9: 1 to 2:1 ) to give compound 72 (0.65 g, yield 61 percent) as a colorless oil. HNMR (CDCI3): δ 4.15(2H, q, J=7.0Hz), 3.62(2H, s), 1.28-1.23(5H, m), 0.86(2H, q, J=4.2Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.65 g | Stage #1: With triethylamine In tetrahydrofuran at -10 - 0℃; for 1 h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 1 h; |
[0371] To a stirring solution of compound 71 (1.0 g, 6.32mmol) and triethylamine (0.97 ml, 7.59 mmol) in THF (18ml) at -10° C., was added isobutyl chloroformate (0.90 ml,6.96 mmol) dropwise. Then the reaction mixture was stirred1 h at oo C., the insoluble material was filtered off, and thefiltrate was directly used later. To an ice-cooling solution ofNaBH4 (0.71 g, 18.97 mmol) in THF (10 ml) and water (2.5ml), was added the filtrate obtained above dropwise. After thereaction mixture was allowed to stirred at oo C. for 1 h, thenreaction mixture was poured into 10percent of aqueous solutionHOAc, the aqueous phase was extracted with EtOAc (30mlx3), and the combined organic phase was washed withbrine, dried over Na2S04 , filtered and concentrated to affordcrude product, which was purified by silica gel column chromatography(Petroleum ether: ethyl acetate=9: 1 to 2:1) to givecompound 72 (0.65 g, yield 61 percent) as a colorless oil.[0372] 1HNMR (CDCI3): ll 4.15 (2H, q, 1=7.0 Hz), 3.62(2H, s), 1.28-1.23 (5H, m), 0.86 (2H, q, 1=4.2 Hz) |
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