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CAS No.: | 5950-12-9 |
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Name: | piperlonguminine |
Article Data: | 11 |
Molecular Structure: | |
Formula: | C16H19 N O3 |
Molecular Weight: | 273.332 |
Synonyms: | 2,4-Pentadienamide,5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (E,E)-; Piperamide, N-isobutyl-(8CI); Piperlonguminine (7CI); N-Isobutylpiperamide; NSC 125178;Piperlonguminin |
Density: | 1.136g/cm3 |
Boiling Point: | 476.9°C at 760 mmHg |
Flash Point: | 242.2°C |
PSA: | 47.56000 |
LogP: | 3.14780 |
Conditions | Yield |
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Stage #1: piperic acid With thionyl chloride In dichloromethane for 1h; Reflux; Stage #2: isobutylamine In dichloromethane for 1h; | 93% |
With boric acid In toluene for 16h; Heating; | 91% |
With dmap; dicyclohexyl-carbodiimide Amidation; | 76% |
With methanesulfonyl chloride; triethylamine 1.) CH2Cl2, 45 min., 0 deg C ; 2.) 2h, 0-25 deg C; Yield given. Multistep reaction; |
Conditions | Yield |
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With triethylamine at 20℃; for 5h; Cooling with ice; | 86% |
With triethylamine In tetrahydrofuran at 60℃; Acylation; | 83% |
(E)-5-Benzo[1,3]dioxol-5-yl-5-hydroxy-pent-2-enoic acid isobutyl-amide
piperlonguminine
Conditions | Yield |
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With pyridine; methanesulfonyl chloride Ambient temperature; | 84% |
2-[(E)-3,4-(methylenedioxy)cinnamylsulfonyl]-N-isobutylacetamide
piperlonguminine
Conditions | Yield |
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With aluminum oxide; potassium hydroxide; dibromodifluoromethane In dichloromethane at 20℃; for 1h; | 84% |
Conditions | Yield |
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In neat (no solvent) at 20℃; for 0.5h; | 74% |
3,4-methylenedioxy-trans-cinnamic acid
N-(2-methylpropyl)prop-2-enamide
piperlonguminine
Conditions | Yield |
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Stage #1: 3,4-methylenedioxy-trans-cinnamic acid With N-Bromosuccinimide; tetrabutylammonium trifluoroacetate In 1,2-dichloro-ethane at 20℃; for 4h; Decarboxylation; bromination; Hunsdiecker reaction; Stage #2: N-(2-methylpropyl)prop-2-enamide With palladium diacetate; triphenylantimony; triethylamine In 1,2-dichloro-ethane for 20h; Heck reaction; | 34% |
Conditions | Yield |
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In dichloromethane at 0 - 20℃; for 3h; | 120 mg |
thioacetic acid S-(3-benzo[1,3]dioxol-5-yl-allyl) ester
piperlonguminine
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: KOH / methanol / 0.17 h / 0 °C 1.2: 68 percent / methanol / 1 h / 0 °C 2.1: 94 percent / oxone / methanol; H2O / 0 °C 3.1: 84 percent / KOH; Al2O3; CBr2F2 / CH2Cl2 / 1 h / 20 °C View Scheme |
2-[(E)-3,4-(methylenedioxy)cinnamylthio]-N-isobutylacetamide
piperlonguminine
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 94 percent / oxone / methanol; H2O / 0 °C 2: 84 percent / KOH; Al2O3; CBr2F2 / CH2Cl2 / 1 h / 20 °C View Scheme |
Conditions | Yield |
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Multi-step reaction with 6 steps 1.1: benzene / 4 h / Heating 2.1: LiAlH4; AlCl3 / tetrahydrofuran / 1 h / 0 °C 3.1: 83 percent / DIAD; Ph3P / benzene / 1 h / 20 °C 4.1: KOH / methanol / 0.17 h / 0 °C 4.2: 68 percent / methanol / 1 h / 0 °C 5.1: 94 percent / oxone / methanol; H2O / 0 °C 6.1: 84 percent / KOH; Al2O3; CBr2F2 / CH2Cl2 / 1 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: NaH / dimethylformamide / 4 h / 30 - 35 °C 1.2: 94 percent / dimethylformamide / 16 h / 20 °C 2.1: 100 percent / KOH / methanol / 6 h / Heating 3.1: 91 percent / B(OH)3 / toluene / 16 h / Heating View Scheme |