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CAS No. : | 101080-22-2 | MDL No. : | MFCD13659410 |
Formula : | C6H10O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XWWQLKYMTLWXKN-UHFFFAOYSA-N |
M.W : | 130.14 | Pubchem ID : | 15153193 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.83 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 31.78 |
TPSA : | 57.53 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) : | -7.1 cm/s |
Log Po/w (iLOGP) : | 0.94 |
Log Po/w (XLOGP3) : | -0.01 |
Log Po/w (WLOGP) : | 0.23 |
Log Po/w (MLOGP) : | 0.0 |
Log Po/w (SILICOS-IT) : | 0.16 |
Consensus Log Po/w : | 0.26 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.57 |
Solubility : | 34.7 mg/ml ; 0.266 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.75 |
Solubility : | 23.2 mg/ml ; 0.178 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.43 |
Solubility : | 351.0 mg/ml ; 2.7 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.56 |
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 |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; sodium tetrahydroborate at 20℃; Cooling with ice; | 32.A Step A: 3-hydroxylcyclopentane carboxylic acid To a solution of 3-carbonylcyclopentane carboxylic acid (3.7 g, 28.9 mmol) in methanol was added sodium borohydride (1.64 g, 43.2 mmol) in batches in an ice bath. After the addition was completed, the reaction mixture was stirred at room temperature. After the reaction was completed, 1M hydrochloric acid solution was added to the reaction liquid to quench the reaction. The solvent was removed to give a crude product which was directly used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / 90 °C 2: 1H-imidazole / N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sulfuric acid / 90 °C 2: 1H-imidazole / N,N-dimethyl-formamide 3: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C | ||
Multi-step reaction with 3 steps 1: sulfuric acid / 90 °C 2: 1H-imidazole / N,N-dimethyl-formamide 3: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sulfuric acid / 90 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide 3.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.25 h / 20 °C / Cooling with ice 4.2: 1 h / 0 - 20 °C | ||
Multi-step reaction with 4 steps 1.1: sulfuric acid / 90 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide 3.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.25 h / 20 °C / Cooling with ice 4.2: 1 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sulfuric acid / 90 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide 3.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.25 h / 20 °C / Cooling with ice 4.2: 1 h / 0 - 20 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 72 h / 20 °C | ||
Multi-step reaction with 6 steps 1.1: sulfuric acid / 90 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide 3.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.25 h / 20 °C / Cooling with ice 4.2: 1 h / 0 - 20 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 15 h / 65 °C 6.1: trifluoroacetic acid / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / 90 °C 2: diethylamino-sulfur trifluoride / tetrahydrofuran / 3 h / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.27 g | With sulfuric acid at 90℃; | 32.B Step B: ethyl 3-hydroxylcyclopentane formate To a solution of the crude product obtained from the step A in ethanol was added concentrated sulfuric acid (1.5 mL), and the mixture was reacted overnight at 90°C. After the reaction was completed, the reaction was quenched by adding saturated sodium bicarbonate, and ethanol was removed. Water was added to the concentrate, and the resulting mixture was extracted with ethyl acetate, and column chromatographed (ethyl acetate/petroleum ether = 1/5) to give racemic ethyl 3-hydroxylcyclopentane formate (2.27g, 50% yield). 1HNMR (400MHz, CDCl3) δ 4.30-4.34 (m, 1H), 4.10-4.18 (m, 2H), 2.82-2.90 (m, 1H), 1.60-2.20 (m, 7H), 1.20-1.29 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate In methanol at 20℃; | 1.A Step A: 3-hydroxycyclopentanecarboxylic acid To a solution of 3-carbonylcyclopentanecarboxylic acid (3.7 g, 28.9 mmol)In methanol was added sodium borohydride (1.64 g, 43.2 mmol) in portions,Plus at room temperature stirring until the reaction is completed, the reaction solution was added 1M hydrochloric acid solution,Quench the reaction and remove the solvent to give the crude product the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / 90 °C 2: 1H-imidazole / N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sulfuric acid / 90 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide 3.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.25 h / 20 °C / Cooling with ice 4.2: 1 h / 0 - 20 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 15 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sulfuric acid / 90 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide 3.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.25 h / 20 °C / Cooling with ice 4.2: 1 h / 0 - 20 °C 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 15 h / 65 °C 6.1: trifluoroacetic acid / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere 7.1: manganese(IV) oxide / dichloromethane / 72 h / 20 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.27 g | With sulfuric acid at 90℃; | 1.B Step B: Ethyl 3-hydroxycyclopentanecarboxylate To the crude ethanol solution obtained in Step A, 1.5 mL of concentrated sulfuric acid was added,The reaction was carried out overnight at 90 ° C. After the reaction finishedQuenched by adding saturated sodium bicarbonate to remove ethanol, the concentrate was added to water,Ethyl acetate extraction, column chromatography (ethyl acetate / petroleum ether = 1/5),getRacemic ethyl 3-hydroxycyclopentanecarboxylate (2.27 g, 50% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 16 h / 0 - 20 °C 2: toluene-4-sulfonic acid / toluene / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.8% | With triethylamine In dichloromethane at 0 - 20℃; for 16h; | 3 Synthesis of main chain degradable photoresist resin monomers 3-3 3-hydroxycyclopentanoic acid 3-1 (25g, 192mmol) was added to dichloromethane (250mL), then triethylamine (48.6g, 480mmol) was added, the reaction solution was cooled to 0°C in an ice-water bath, and slowly acryloyl chloride (17.4g, 192mmol) was added dropwise, the reaction solution was raised to room temperature and stirred for 16 hours. The reaction solution was slowly added to ice water (200mL) for quenching, and the pH was adjusted to weakly acidic with 2.5M dilute hydrochloric acid. It was extracted three times with ethyl acetate (150mL*3), the organic phases were combined and washed with saturated brine (100mL). The organic phase was spin-dried under vacuum to obtain Intermediate 3-2 (30g, 163mmol, yield: 84.8%) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 85℃; | General Procedure for the preparation of compounds 1-42 General procedure: All target compounds were synthesizedthrough the condensation reaction between carboxylic acid derivatives and benzothiazolamide (m4) underthe action of HATU (Scheme 1) |
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