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CAS No. : | 110928-44-4 | MDL No. : | MFCD03840884 |
Formula : | C9H16O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 172.22 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.89 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 45.71 |
TPSA : | 46.53 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) : | -6.74 cm/s |
Log Po/w (iLOGP) : | 2.18 |
Log Po/w (XLOGP3) : | 0.86 |
Log Po/w (WLOGP) : | 0.96 |
Log Po/w (MLOGP) : | 1.0 |
Log Po/w (SILICOS-IT) : | 1.23 |
Consensus Log Po/w : | 1.25 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.25 |
Solubility : | 9.65 mg/ml ; 0.056 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.42 |
Solubility : | 6.54 mg/ml ; 0.038 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.99 |
Solubility : | 17.7 mg/ml ; 0.103 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.43 |
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 |
---|---|---|
100% | Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -65℃; for 0.5 h; Stage #2: With triethylamine In dichloromethane at -65℃; for 0.25 h; |
trans-4-Formyl-cyclohexanecarboxylic acid methyl ester To a solution of dimethylsulfoxide (9.53 g, 122 mmol) in dry dichloromethane (400 ml) was slowly added oxalyl chloride (7.74 g, 61.0 mmol) at -78° C. The cooling bath was removed and the reaction mixture was stirred at -50° C. for 5 min. A solution of trans-4-hydroxymethyl-cyclohexanecarboxylic acid methyl ester (8.75 g, 50.8 mmol) in dichloromethane (108 ml) was added at -65° C. Stirring for 30 minutes was followed by addition of triethylamine (25.7 g, 254 mmol). The cooling bath was removed 15 minutes after completed addition. The reaction mixture was quenched with 1 M aqueous hydrochloric acid solution (152 ml, 152 mmol) at -10° C. The layers were separated. The organic layer was washed with two 250 ml-portions of water and one 100-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as yellow oil (9.3 g, quantitative), which was used in the next step without further purification. MS m/e: 170 (M+) |
91% | Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃; for 1.75 h; Stage #2: With triethylamine In dichloromethane at -60 - 0℃; for 1.5 h; |
(4) Under argon gas atmosphere to a solution of oxalyl chloride (4.48 mL) in methylene chloride (50 mL) was added dropwise a solution of dimethysulfoxide (4.55 g) in methylene chloride (5 mL) at -60 °C and the mixture was stirred at the same temperature for 15 minutes. To the mixture was added dropwise a solution of the compound obtained in the above step (3) (5.9 g) in methylene chloride (30 mL) over a period of 30 minutes and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added dropwise triethylamine (16.7 mL) at -60 °C and the mixture was stirred at the same temperature for 30 minutes and then stirred at 0 °C for 1 hour. The reaction mixture was diluted with chloroform, washed successively with water, an aqueous 5 percent citric acid, water and brine, dried over sodium sulfate and concentrated in vacuo to give methyl trans-4-formylcyclohexanecarboxylate (5.32 g, yield: 91 percent) as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: With borane-THF In tetrahydrofuran at -50 - -10℃; for 2 h; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran at 0℃; |
(3) Under argon gas atmosphere to a solution of momomethyl trans-cyclohexane-1,4-dicarboxylate (14.3 g) in tetrahydrofuran (78 mL) was added dropwise 1.0 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (100 mL) at -50 °C over a period of 1 hour and the mixture was stirred at -10 °C for 1 hour. To the reaction mixture was added water (160 mL) and an aqueous saturated sodium hydrogencarbonate solution (160 mL) under ice-cooling and the mixture was extracted with ethyl acetate (160 mL x 4). The extract was washed with brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by a flash column chromatography on silica gel (Solvent; chloroform/methanol = 20: 1) to give methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (13.25 g, yield: 100 percent) as an oil. MS(APCI)m/z; 173 [M+H]+ |
94.6% | With dimethylsulfide borane complex In tetrahydrofuran at 0℃; for 4.25 h; | trans-4-Hydroxymethyl-cyclohexanecarboxylic acid methyl ester To a solution of trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (10.0 g, 53.7 mmol) in tetrahydrofuran (540 ml) was added borane-dimethylsulfide complex (6.80 g, 80.6 mmol) at 0-5° C. The cooling bath was removed after 15 minutes and the mixture was stirred for 4 h. The reaction mixture was quenched with methanol (17.2 g, 537 mmol), stirred for 20 minutes and concentrated in vacuo. The residue was triturated in tert-butyl methyl ether (300 ml) and filtrated over a pad of Decalite. The filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate (300 ml) and 1 M aqueous sodium hydroxide solution (100 ml). The layers were separated. The organic layer was washed with one 100 ml-portion of water. The combined aqueous layers were extracted with one 150-ml portion of ethyl acetate. The combined organic layers were washed with one 50 ml-portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (8.75 g, 94.6percent) as colorless oil, which can be used without further purification. MS m/e: 172 (M+) |
87% | With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 2 h; | The (100 mL) trans-cyclohexane-1,4-dicarboxylic acid monomethyl ester (5.00g, 26.8mmol) was dissolved in tetrahydrofuran, was added at 0°C borane dimethyl sulfide (3.06g, 40.3mmol), reaction at room temperature for 2 hours. Was added a saturated methanol (50 mL) to quench the reaction. After the condensed water (50mL) and extracted with ethyl acetate (10mLx3), dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure to give 4-hydroxymethyl-cyclohexanecarboxylic acid methyl ester (4.00 g, yellow oil). Yield: 87percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With hydrogen In methanol for 3 h; | 4-Benzyloxymethyl-cyclohexanecarboxylic acid methyl ester (340 mg, 1.30 mmol) is dissolved in MeOH (15 mL). In presence of catalytic amount of 10percent Pd/C, the reaction mixture is stirred for 3 hours under hydrogen (10 bar). After removing 10percent Pd/C, solvent is evaporated to obtain trans-4-hydroxymethyl-cyclohexanecarboxylic acid methyl ester as colorless oil (160 mg, 72percent) after purification. 1H-NMR (400 MHz, CDCl3), δ (ppm): 0.99 (m, 2H), 1.47 (m, 3H), 1.88 (m, 2H), 2.02 (m, 2H), 2.23 (m, 1H), 3.46 (d, 2H), 3.66 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | for 4 h; Reflux | Concentrated H2S04 (15 mL) was added to a solution of trans-4- hydroxymethylcyclohexane carboxylic acid 13 (15 g; 94.8 mmol) in MeOH (300 ml_) then the reaction mixture was stirred and refluxed for 4 h . The solution was concentrated under reduced pressure and basified by addition of aq . NH4OH; the white solid was filtered off and the mother liquor was extracted with EtOAc ( 3 x 70 m l_) . The com bined organ ic l ayers were washed with saturated aq . NaCI, dried (Na2S04) and evaporated at reduced pressure to give 14 as a yellow liquid ( 17.26 g) that was employed in the following reaction without further purification. Quantitative yield . Analytical data : Mr: 172.22 (C9H 1603) and 13C-NMR and MS are compatible with the structure |
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