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CAS No.: | 489-39-4 | ||||
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Name: | (+)-AROMADENDRENE | ||||
Article Data: | 6 | ||||
Molecular Structure: | |||||
Formula: | C15H24 | ||||
Molecular Weight: | 204.356 | ||||
Synonyms: | 1H-Cycloprop[e]azulene,decahydro-1,1,7-trimethyl-4-methylene-, (1aR,4aR,7R,7aR,7bS)-(+)- (8CI);1H-Cycloprop[e]azulene, decahydro-1,1,7-trimethyl-4-methylene-, [1aR-(1aa,4aa,7a,7ab,7ba)]-; Aromadendrene (6CI,7CI); (+)-Aromadendrene;10(14)-Aromadendrene; Aromadendr-7(15)-ene; Aromadendrene, (+)-;Decahydro-1,1,7-trimethyl-4-methylene-1H-cycloprop[e]azulene | ||||
Density: | 0.93g/cm3 | ||||
Melting Point: | 262°C | ||||
Boiling Point: |
261-263 °C(lit.) |
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Flash Point: | 106.5°C | ||||
Safety: |
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PSA: | 0.00000 | ||||
LogP: | 4.27090 |
Methanesulfonic acid (1aR,4S,4aR,7R,7aR,7bS)-1,1,7-trimethyl-decahydro-cyclopropa[e]azulen-4-ylmethyl ester
(+)-aromadendrene
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 100℃; for 18h; | 89% |
(1aR,4aR,7R,7aS,7bS)-1,1,7-Trimethyldecahydro-4H-cyclopropa[e]azulen-4-one
Methyltriphenylphosphonium bromide
(+)-aromadendrene
Conditions | Yield |
---|---|
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 0.166667h; Inert atmosphere; Stage #2: (1aR,4aR,7R,7aS,7bS)-1,1,7-Trimethyldecahydro-4H-cyclopropa[e]azulen-4-one In tetrahydrofuran at -78 - 20℃; for 24h; Inert atmosphere; | 60% |
Conditions | Yield |
---|---|
With pyridine; trichlorophosphate |
(+)-aromadendrene
Conditions | Yield |
---|---|
at 140℃; unter vermindertem Druck; |
methyl (+)-(1S,7R)-8,8-dimethyl-3-oxobicyclo<5.1.0>octane-4-carboxylate
(+)-aromadendrene
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1: 100 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 2: imidazole / dimethylformamide / 12 h / Ambient temperature 3: 90 percent / Ley's tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide, molecular sieves / CH2Cl2 / 0.25 h / Ambient temperature 4: 1.) LDA, HMPA / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to RT, 4 h 5: 96 percent / PdCl2, CuCl, air / dimethylformamide; H2O / 4.5 h / Ambient temperature 6: 84 percent / NaHMDS, HMPA / tetrahydrofuran / 0.67 h / -78 - -50 °C / a) -78 deg C. 15 min, b) 0 deg C, 15 min, c) 50 deg C, 10 min 7: 1.) lithium hexamethyldisilazane, HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT, 2 h 8: 86 percent / lithium tetramethyldisilazane, HMPA / tetrahydrofuran / 2 h / -78 - 20 °C 9: 93 percent / H2 / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature 10: NaBH4 / methanol / 2 h / Ambient temperature 11: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 12: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 13: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 14: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 15: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme |
(+)-aromadendrene
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1: imidazole / dimethylformamide / 12 h / Ambient temperature 2: 90 percent / Ley's tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide, molecular sieves / CH2Cl2 / 0.25 h / Ambient temperature 3: 1.) LDA, HMPA / 1.) THF, -78 deg C, 30 min, 2.) THF, from -78 deg C to RT, 4 h 4: 96 percent / PdCl2, CuCl, air / dimethylformamide; H2O / 4.5 h / Ambient temperature 5: 84 percent / NaHMDS, HMPA / tetrahydrofuran / 0.67 h / -78 - -50 °C / a) -78 deg C. 15 min, b) 0 deg C, 15 min, c) 50 deg C, 10 min 6: 1.) lithium hexamethyldisilazane, HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT, 2 h 7: 86 percent / lithium tetramethyldisilazane, HMPA / tetrahydrofuran / 2 h / -78 - 20 °C 8: 93 percent / H2 / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature 9: NaBH4 / methanol / 2 h / Ambient temperature 10: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 11: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 12: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 13: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 14: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme |
(+)-aromadendrene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 2: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 3: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 4: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 5: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme |
(+)-(1S,2S,4R,7R)-4-tert-butyldimethylsiloxymethyl-8,8-dimethyl-2-(2-propenyl)bicyclo<5.1.0>octan-3-one
(+)-aromadendrene
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 96 percent / PdCl2, CuCl, air / dimethylformamide; H2O / 4.5 h / Ambient temperature 2: 84 percent / NaHMDS, HMPA / tetrahydrofuran / 0.67 h / -78 - -50 °C / a) -78 deg C. 15 min, b) 0 deg C, 15 min, c) 50 deg C, 10 min 3: 1.) lithium hexamethyldisilazane, HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT, 2 h 4: 86 percent / lithium tetramethyldisilazane, HMPA / tetrahydrofuran / 2 h / -78 - 20 °C 5: 93 percent / H2 / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature 6: NaBH4 / methanol / 2 h / Ambient temperature 7: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 8: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 9: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 10: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 11: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme |
(+)-(1R,2S,4R,7S,8R,11S)-7-tert-butyldimethylsiloxymethyl-3,3,11-trimethyltricyclo<6.3.0.02,4>undecan-10-one
(+)-aromadendrene
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: NaBH4 / methanol / 2 h / Ambient temperature 2: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 3: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 4: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 5: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 6: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme |
(+)-(1R,2R,4R,7S)-7-tert-butyldimethylsiloxymethyl-3,3-dimethyltricyclo<6.3.0.02,4>undec-8-en-10-one
(+)-aromadendrene
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 1.) lithium hexamethyldisilazane, HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT, 2 h 2: 86 percent / lithium tetramethyldisilazane, HMPA / tetrahydrofuran / 2 h / -78 - 20 °C 3: 93 percent / H2 / 5percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature 4: NaBH4 / methanol / 2 h / Ambient temperature 5: pyridine, DMAP / CH2Cl2 / 6 h / Ambient temperature 6: 68 percent / n-Bu3SnH, AIBN / toluene / 3 h / Heating 7: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature 8: 100 percent / Et3N, DMAP / CH2Cl2 / 2 h / 0 °C 9: 89 percent / DBU / toluene / 18 h / 100 °C View Scheme |