Name: (+)-AROMADENDRENE
SKU: 489-39-4

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Basic Information

CAS No.:

489-39-4

Name:

(+)-AROMADENDRENE

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.)

Flash Point:

106.5°C

Safety:

WGK Germany	3
F	10-23

PSA:

0.00000

LogP:

4.27090

Synthetic route

: 175985-51-0
Methanesulfonic acid (1aR,4S,4aR,7R,7aR,7bS)-1,1,7-trimethyl-decahydro-cyclopropa[e]azulen-4-ylmethyl ester

: 489-39-4
(+)-aromadendrene

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 100℃; for 18h;	89%

: 99147-41-8
(1aR,4aR,7R,7aS,7bS)-1,1,7-Trimethyldecahydro-4H-cyclopropa[e]azulen-4-one

: 1779-49-3
Methyltriphenylphosphonium bromide

: 489-39-4
(+)-aromadendrene

Conditions

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%

: 489-41-8
(-)-globulol

: 489-39-4
(+)-aromadendrene

Conditions

Conditions	Yield
With pyridine; trichlorophosphate

(-)-O-<3,5-dinitro-benzoyl>-globulol: (-)-O-<3,5-dinitro-benzoyl>-globulol

: 489-39-4
(+)-aromadendrene

Conditions

Conditions	Yield
at 140℃; unter vermindertem Druck;

: 176199-11-4
methyl (+)-(1S,7R)-8,8-dimethyl-3-oxobicyclo<5.1.0>octane-4-carboxylate

: 489-39-4
(+)-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

: (1S,7R)-4-Hydroxymethyl-8,8-dimethyl-bicyclo[5.1.0]octan-3-ol

: 489-39-4
(+)-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

: (1aR,4S,4aR,7S,7aR,7bS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-1,1,7-trimethyl-decahydro-cyclopropa[e]azulen-6-ol

: 489-39-4
(+)-aromadendrene

Conditions

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

: 175985-40-7
(+)-(1S,2S,4R,7R)-4-tert-butyldimethylsiloxymethyl-8,8-dimethyl-2-(2-propenyl)bicyclo<5.1.0>octan-3-one

: 489-39-4
(+)-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

: 175985-45-2
(+)-(1R,2S,4R,7S,8R,11S)-7-tert-butyldimethylsiloxymethyl-3,3,11-trimethyltricyclo<6.3.0.02,4>undecan-10-one

: 489-39-4
(+)-aromadendrene

Conditions

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

: 175985-44-1
(+)-(1R,2R,4R,7S)-7-tert-butyldimethylsiloxymethyl-3,3-dimethyltricyclo<6.3.0.02,4>undec-8-en-10-one

: 489-39-4
(+)-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