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[ CAS No. 28282-25-9 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 28282-25-9
Chemical Structure| 28282-25-9
Structure of 28282-25-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 28282-25-9 ]

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

Calculated chemistry of [ 28282-25-9 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 5.77

Safety of [ 28282-25-9 ]

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:

Application In Synthesis of [ 28282-25-9 ]

* 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.

  • Downstream synthetic route of [ 28282-25-9 ]

[ 28282-25-9 ] Synthesis Path-Downstream   1~43

  • 1
  • [ 908094-01-9 ]
  • [ 28282-25-9 ]
  • [ 28282-56-6 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether β-elemonic acid methyl ester substance of unknown configurative homogeneity;
  • 2
  • [ 28282-25-9 ]
  • [ 28368-21-0 ]
YieldReaction ConditionsOperation in experiment
With ethanol; hydrazine hydrate anschliessendes Erhitzen mit Natriumamylat in Amylalkohol auf 180grad;
  • 3
  • [ 28282-25-9 ]
  • 25-bromo-3-oxo-tirucallen-(8)-oic acid-(21) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With chloroform; hydrogen bromide
  • 4
  • [ 28282-25-9 ]
  • 3-hydroxyimino-tirucalla-8,24-dien-21-oic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
β-elemonic acid-oxime substance of unknown configurative homogeneity;
  • 5
  • [ 28282-25-9 ]
  • 24ξ,25-dibromo-3-oxo-tirucallen-(8)-oic acid-(21) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With chloroform; bromine
  • 6
  • [ 28282-25-9 ]
  • 3,3'-azino-di-tirucalla-8,24-dien-21-oic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With girard's reagent T; acetic acid β-elemonic acid azinesubstance of unknown configurative homogeneity;
  • 7
  • [ 28282-25-9 ]
  • tirucallen-(8)-oic acid-(21) [ No CAS ]
YieldReaction ConditionsOperation 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
  • 8
  • [ 28282-25-9 ]
  • [ 115788-11-9 ]
YieldReaction ConditionsOperation in experiment
With ethanol; acetic acid; platinum Hydrogenation;
YieldReaction ConditionsOperation in experiment
entspr. Ester (V), KOH;
  • 14
  • [ 82509-40-8 ]
  • [ 28282-25-9 ]
YieldReaction ConditionsOperation in experiment
at 270 - 300℃;
  • 15
  • [ 28282-25-9 ]
  • 21.24-cyclo-20ξ<i>H</i>-tirucalladiene-(8.24)-dione-(3.21) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With phosphorus pentoxide; benzene stereoisomer(ic) of mp: 183 degree;
  • 16
  • [ 28282-25-9 ]
  • 21.24-cyclo-20ξ<i>H</i>-tirucalladiene-(8.24)-dione-(3.21) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With phosphorus pentoxide; benzene stereoisomer(ic) of mp: 168 degree;
YieldReaction ConditionsOperation in experiment
at 20℃;
YieldReaction ConditionsOperation in experiment
Siedetemperatur;
YieldReaction ConditionsOperation in experiment
Hydrogenation;
YieldReaction ConditionsOperation in experiment
Hydrogenation;
YieldReaction ConditionsOperation in experiment
Hydrogenation;
YieldReaction ConditionsOperation in experiment
Hydrogenation;
YieldReaction ConditionsOperation in experiment
Hydrogenation;
YieldReaction ConditionsOperation in experiment
at 125℃; Hydrogenation;
  • 27
  • [ 28282-25-9 ]
  • 13α.14β.17β<i>H</i>.20βF<i>H</i>-lanostadiene-(8.24)-diol-(3ξ.21) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diethyl ether 2: amyl alcohol; sodium
  • 28
  • [ 28282-25-9 ]
  • tirucallen-(8)-oic acid-(21)-methyl ester [ No CAS ]
YieldReaction ConditionsOperation 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
  • 29
  • [ 28282-25-9 ]
  • methyl 3-oxotirucall-8-en-21-oate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: platinum; ethanol / Hydrogenation 2: diethyl ether
  • 30
  • [ 28282-25-9 ]
  • N-((E)-2-(3-oxo-tirucall-1,8,24-trien-21-((benzyloxy)carbonyl)-2(1H)-ethylidene)-carbonyl)-piperazine [ No CAS ]
YieldReaction ConditionsOperation 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
  • 31
  • [ 28282-25-9 ]
  • N-((E)-2-(3-oxo-tirucall-1,8,24-trien-21-((benzyloxy)carbonyl)-2(1H)-ethylidene)-carbonyl)-N-methyl piperazine [ No CAS ]
YieldReaction ConditionsOperation 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
  • 32
  • [ 28282-25-9 ]
  • 3-oxo-25,26,27-trinortirucall-8,24-dien-21-((benzyloxy)carbonyl)-24-amine [ No CAS ]
YieldReaction ConditionsOperation 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
  • 33
  • [ 28282-25-9 ]
  • 3-oxo-25,26,27-trinortirucall-8,24-dien-21-((benzyloxy)carbonyl)-24-nitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 34
  • [ 28282-25-9 ]
  • 3-oxo-25,26,27-trinortirucall-8,24-dien-21-((benzyloxy)carbonyl)-24-tetrazole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 35
  • [ 28282-25-9 ]
  • C34H45ClO4 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 36
  • [ 28282-25-9 ]
  • C39H51ClO4 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 37
  • [ 28282-25-9 ]
  • 3-oxo-25,26,27-trinortirucall-8,24-dien-21-((benzyloxy)carbonyl)-24-carboxylic acid [ No CAS ]
  • 3,7-dioxo-25,26,27-trinortirucall-8,24-dien-21-((benzyloxy)carbonyl)-24-carboxylic acid [ No CAS ]
  • 3,11-dioxo-25,26,27-trinortirucall-8,24-dien-21-((benzyloxy)carbonyl)-24-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation 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
  • 38
  • [ 28282-25-9 ]
  • N-(3-oxo-25,26,27-trinortirucall-8,24-dien-21-((benzyloxy)carbonyl)-24-carbonyl)-piperazine [ No CAS ]
YieldReaction ConditionsOperation 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
  • 39
  • [ 28282-25-9 ]
  • N-(3-oxo-25,26,27-trinortirucall-8,24-dien-21-((benzyloxy)carbonyl)-24-carbonyl)-N-methyl piperazine [ No CAS ]
YieldReaction ConditionsOperation 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
  • 40
  • [ 28282-25-9 ]
  • N,N-(3-oxo-25,26,27-trinortirucall-8,24-dien-21-((benzyloxy)carbonyl)-24-carbonyl)-dimethylamine [ No CAS ]
YieldReaction ConditionsOperation 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
  • 41
  • [ 28282-25-9 ]
  • methyl 3-oxo-25,26,27-trinortirucall-8,24-dien-21-((benzyloxy)carbonyl)-24-oate [ No CAS ]
YieldReaction ConditionsOperation 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
  • 42
  • [ 28282-25-9 ]
  • (E)-2-(3-oxo-tirucall-1,8,24-trien-21-((benzyloxy)carbonyl)-2(1H)-ethylidene)-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 3 h / 100 °C 2: sodium hydroxide / water; ethanol / 8 h / 90 °C
  • 43
  • [ 28282-25-9 ]
  • [ 100-39-0 ]
  • benzyl 3-oxo-tirucall-8,24-dien-21-oate [ No CAS ]
YieldReaction ConditionsOperation 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)+.
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