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CAS No. : | 28282-25-9 | MDL No. : | |
Formula : | C30H46O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 454.68 | Pubchem ID : | - |
Synonyms : |
Elemadienonic Acid;3-Oxotirucallenoic Acid;3-oxo Tirucallic Acid;Beta-Elemonic acid
|
Chemical Name : | Beta-elemonicacid |
Num. heavy atoms : | 33 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 137.85 |
TPSA : | 54.37 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.0 cm/s |
Log Po/w (iLOGP) : | 3.78 |
Log Po/w (XLOGP3) : | 7.15 |
Log Po/w (WLOGP) : | 7.75 |
Log Po/w (MLOGP) : | 5.63 |
Log Po/w (SILICOS-IT) : | 7.33 |
Consensus Log Po/w : | 6.33 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -6.83 |
Solubility : | 0.0000667 mg/ml ; 0.000000147 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -8.11 |
Solubility : | 0.00000351 mg/ml ; 0.0000000077 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -6.85 |
Solubility : | 0.0000642 mg/ml ; 0.000000141 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 5.77 |
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 |
---|---|---|
With diethyl ether β-elemonic acid methyl ester substance of unknown configurative homogeneity; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol; hydrazine hydrate anschliessendes Erhitzen mit Natriumamylat in Amylalkohol auf 180grad; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chloroform; hydrogen bromide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
β-elemonic acid-oxime substance of unknown configurative homogeneity; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chloroform; bromine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With girard's reagent T; acetic acid β-elemonic acid azinesubstance of unknown configurative homogeneity; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; amalgamated zinc; acetic acid | ||
Multi-step reaction with 2 steps 1: platinum; acetic acid / Hydrogenation 2: hydrazine hydrate; ethanolic sodium ethylate / 200 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol; acetic acid; platinum Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium on activated charcoal; acetic acid Hydrogenation; | ||
With ethyl acetate; platinum Hydrogenation; | ||
With ethanol; platinum Hydrogenation; |
With acetic acid; platinum Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
entspr. Ester (V), KOH; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 270 - 300℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus pentoxide; benzene stereoisomer(ic) of mp: 183 degree; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus pentoxide; benzene stereoisomer(ic) of mp: 168 degree; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Siedetemperatur; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 125℃; Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: diethyl ether 2: amyl alcohol; sodium |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: amalgamated zinc; aqueous hydrochloric acid; acetic acid 2: diethyl ether | ||
Multi-step reaction with 3 steps 1: platinum; acetic acid / Hydrogenation 2: hydrazine hydrate; ethanolic sodium ethylate / 200 °C 3: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: platinum; ethanol / Hydrogenation 2: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / 3 h / 100 °C 2: sodium hydroxide / water; ethanol / 8 h / 90 °C 3: oxalyl dichloride / dichloromethane / 0.5 h 4: 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / 3 h / 100 °C 2: sodium hydroxide / water; ethanol / 8 h / 90 °C 3: oxalyl dichloride / dichloromethane / 0.5 h 4: 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / 3 h / 100 °C 2: potassium carbonate; potassium permanganate; sodium periodate / water; <i>tert</i>-butyl alcohol / 24 h / 30 - 60 °C 3: oxalyl dichloride / dichloromethane / 0.5 h 4: ammonia / dichloromethane; tetrahydrofuran / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / 3 h / 100 °C 2: potassium carbonate; potassium permanganate; sodium periodate / water; <i>tert</i>-butyl alcohol / 24 h / 30 - 60 °C 3: oxalyl dichloride / dichloromethane / 0.5 h 4: ammonia / dichloromethane; tetrahydrofuran / 0.5 h / 20 °C 5: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: potassium carbonate / 3 h / 100 °C 2: potassium carbonate; potassium permanganate; sodium periodate / water; <i>tert</i>-butyl alcohol / 24 h / 30 - 60 °C 3: oxalyl dichloride / dichloromethane / 0.5 h 4: ammonia / dichloromethane; tetrahydrofuran / 0.5 h / 20 °C 5: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 2 h / 0 - 20 °C 6: sodium azide; triethylamine hydrochloride / 1-methyl-pyrrolidin-2-one / 3 h / 150 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / 3 h / 100 °C 2: potassium carbonate; potassium permanganate; sodium periodate / water; <i>tert</i>-butyl alcohol / 24 h / 30 - 60 °C 3: oxalyl dichloride / dichloromethane / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / 3 h / 100 °C 2: sodium hydroxide / water; ethanol / 8 h / 90 °C 3: oxalyl dichloride / dichloromethane / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / 3 h / 100 °C 2: potassium carbonate; potassium permanganate; sodium periodate / water; <i>tert</i>-butyl alcohol / 24 h / 30 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / 3 h / 100 °C 2: potassium carbonate; potassium permanganate; sodium periodate / water; <i>tert</i>-butyl alcohol / 24 h / 30 - 60 °C 3: oxalyl dichloride / dichloromethane / 0.5 h 4: 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / 3 h / 100 °C 2: potassium carbonate; potassium permanganate; sodium periodate / water; <i>tert</i>-butyl alcohol / 24 h / 30 - 60 °C 3: oxalyl dichloride / dichloromethane / 0.5 h 4: 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / 3 h / 100 °C 2: potassium carbonate; potassium permanganate; sodium periodate / water; <i>tert</i>-butyl alcohol / 24 h / 30 - 60 °C 3: oxalyl dichloride / dichloromethane / 0.5 h 4: 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / 3 h / 100 °C 2: potassium carbonate; potassium permanganate; sodium periodate / water; <i>tert</i>-butyl alcohol / 24 h / 30 - 60 °C 3: oxalyl dichloride / dichloromethane / 0.5 h 4: 0.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / 3 h / 100 °C 2: sodium hydroxide / water; ethanol / 8 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.1% | With potassium carbonate at 100℃; for 3h; | 1.1. Benzyl 3-oxo-tirucall-8,24-dien-21-oate (2) A mixture of 1 (1.8 g, 3.9 mmol), BrBn (0.5 mL, 4.2 mmol) and K2CO3 (1.1g, 8.0 mmol) were stirred at 100 °C for 3 h, cooled to room temperature and then poured into water (100 mL). The precipitate was filtered, washed with water to pH 7 and dried Then the product was purified by column chromatography on silica gel with cyclohexane : acetone (v:v) = 200:1, affording the desired product 2. Yield 96.1%, M.p.: 75.6-77.0 °C. IR (KBr): 3433.2, 2958.9, 2870.7, 1726.3, 1703.0, 1455.1, 1377.0, 1138.9, 755.4, 701.7 cm-1. 1H NMR (CDCl3): δ 7.37 (5H, m, -CH2Ph),5.14 (1H, d, J=12.3 Hz, -CH2Ph), 5.06 (1H, d, J=12.3 Hz, -CH2Ph), 5.06 (1H, m,H24), 2.55 (1H, m, H2), 2.46 (1H, m, H2), 2.33 (1H, m, H20), 1.66 (3H, s), 1.51 (3H,s), 1.09 (3H, s), 1.05 (3H, s), 1.03 (3H, s), 0.87 (3H, s), 0.77 (3H, s). LC-MS: 545.3(M+H)+, 567.3 (M+Na)+. |