(+)-Longifolene supplier | CasNO.475-20-7

Name
(+)-Longifolene
EINECS 207-491-2
CAS No. 475-20-7
Article Data14
CAS DataBase
Density 0.93 g/cm³
Solubility 7.9mg/L at 24℃
Melting Point
Formula C₁₅H₂₄
Boiling Point 252.2 °C at 760 mmHg
Molecular Weight 204.356
Flash Point 102.2 °C
Transport Information
Appearance Light-yellowish oil-shaped liquid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,4-Methanoazulene,decahydro-4,8,8-trimethyl-9-methylene-, (1S,3aR,4S,8aS)-(+)- (8CI); 1,4-Methanoazulene,decahydro-4,8,8-trimethyl-9-methylene-, [1S-(1a,3ab,4a,8ab)]-; Longifolene (6CI); (+)-Longifolene; Junipen;Junipene; Kuromatsuen; Kuromatsuene; Longifolen; NSC 150808; d-Longifolene; a-Longifolene
PSA 0.00000
LogP 4.41500

Synthetic route

: 143-33-9
sodium cyanide

: 4678-06-2, 4678-07-3
[(1R,2S,7S,8S,9S)-3,3,7-trimethyltricyclo[5.4.0.02,9]undec-8-yl]methyl 4-methylbenzenesulfonate

A: 943033-63-4
[(1R,2S,7R,8S,9R)-3,3,7-trimethyltricyclo[5.4.0.02,9]undec-8-yl]acetonitrile

B: 475-20-7
longifolene

Conditions

Conditions	Yield
sodium iodide In dimethyl sulfoxide at 90℃; for 24h;	A 69% B 21%

...Expand

: 465-24-7, 16846-28-9, 18374-92-0, 27551-75-3, 51897-51-9
(+)-isolongiborneol

: 475-20-7
longifolene

Conditions

Conditions	Yield
With dmap; methanesulfonyl chloride In pyridine at 105℃; for 16h;	66%

: 18367-70-9
(-)-(1R)(2R)(7S)(8R)(9S)-3,3,7-Trimethyl-8-(acetoxymethyl)tricyclo<5.4.01,7.02,9>undecane

: 475-20-7
longifolene

Conditions

Conditions	Yield
In benzene at 525℃;	56%

: 99481-28-4
10-keto-longifolene

: 475-20-7
longifolene

Conditions

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In diethylene glycol for 4h; Heating;	55%

: 82053-87-0
Trimethyl-((1S,3aR,4S,8aS,9S)-4,8,8-trimethyl-decahydro-1,4-methano-azulen-9-ylmethyl)-ammonium; iodide

A: 475-20-7
longifolene

B: 82053-85-8
N,N-Dimethylisolongifolamine

Conditions

Conditions	Yield
With silver(l) oxide 1.) aq. MeOH, 30 deg C, 3 h; 2.) pyrolyse (oil-bath(250 deg C), 40 mm); Yield given. Multistep reaction;	A n/a B 54%
With silver(l) oxide 1.) aq. MeOH, 30 deg C, 3 h; 2.) pyrolyse (oil-bath(250 deg C), 40 mm); Yield given. Multistep reaction;	A 10% B n/a

: 4678-06-2, 4678-07-3
[(1R,2S,7S,8S,9S)-3,3,7-trimethyltricyclo[5.4.0.02,9]undec-8-yl]methyl 4-methylbenzenesulfonate

A: 475-20-7
longifolene

B: 1135-66-6
(-)-isolongifolene

Conditions

Conditions	Yield
With aluminum oxide In Petroleum ether for 12h;	A 2 g B 9%

: 5989-08-2
(+)-α-Longipinene

A: 1461-03-6
β-himachalene

B: 3853-83-6
α-himachalene

C: 475-20-7
longifolene

D: 1135-66-6
(-)-isolongifolene

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether at 18 - 29℃; for 7h;	A 10 % Chromat. B 46 % Chromat. C 32 % Chromat. D 2 % Chromat.
With boron trifluoride diethyl etherate In diethyl ether at 28 - 29℃; for 7h; Product distribution; other acid, other solvent, other temperature, other time;	A 10 % Chromat. B 46 % Chromat. C 32 % Chromat. D 2 % Chromat.

...Expand

: 5989-08-2
(+)-α-Longipinene

A: 1461-03-6
β-himachalene

B: 475-20-7
longifolene

C: 1135-66-6
(-)-isolongifolene

Conditions

Conditions	Yield
With sulfuric acid In acetic acid at 50 - 51℃; for 1h;	A 52 % Chromat. B 4 % Chromat. C 32 % Chromat.

...Expand

: (1S,3aR,4S,8aR)-4,8,8,9-Tetramethyl-decahydro-1,4-methano-azulen-9-ol

: 475-20-7
longifolene

Conditions

Conditions	Yield
With thionyl chloride In pyridine at 0℃; for 0.166667h; Yield given;

: 3α-Brom-7βH-longifolan

: 475-20-7
longifolene

Conditions

Conditions	Yield
With ethanol at 40 - 60℃; Kinetics;

: 1139-17-9
(-)-Isolongifolol

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81.5 percent / Et3N / DMAP / CH2Cl2 / 0 - 23 °C 2: 21 percent / NaI / dimethylsulfoxide / 24 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1: 4.8 g / pyridine / 1.) 5 deg C, 1 h, 2.) 25 deg C, 12 h 2: 2 g / alumina / petroleum ether / 12 h View Scheme

: 116403-51-1
(-)-longicamphenylone

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether; tetrahydrofuran / 3 h / 50 °C 2: SOCl2 / pyridine / 0.17 h / 0 °C View Scheme

: (-)-(1R,2R,7S,9S)-3,3-dimethyltricyclo<5.4.0.02,9>undecan-8-one

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) lithium cyclohexylisopropylamide / 1.) hexane-THF, -78 deg C, +60 deg C, 1.5 h; 2.) THF, reflux, 16 h 2: diethyl ether; tetrahydrofuran / 3 h / 50 °C 3: SOCl2 / pyridine / 0.17 h / 0 °C View Scheme

: (1R)(2R)(4R)(5R)(7S)(8R)(9S)-3,3,7-Trimethyl-4-methoxy-5-hydroxy-8-(hydroxymethyl)tricyclo<5.4.01,7.02,9>undecane

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 74 percent / pyridine / diethyl ether / 6 h / 0 °C 2: 0.240 g / pyridine / CH2Cl2 / 21 °C 3: Bu3SnH, AIBN / toluene / 4 h / Heating 4: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C 5: pyridine / CH2Cl2 / 3 h / 21 °C 6: Bu3SnH, AIBN / toluene / 5 h / 110 °C 7: 56 percent / benzene / 525 °C View Scheme

: (1R)(2R)(4R)(5R)(7S)(8R)(9S)-3,3,7-Trimethyl-4-methoxy-5-hydroxy-8-(hydroxymethyl)tricyclo<5.4.01,7.02,9>-10-undecene

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: pyridine / diethyl ether / 14 h / 0 °C 2: 67 percent / pyridine / CH2Cl2 / 3 h / 21 °C 3: 89 percent / Bu3SnH, AIBN / toluene / 3 h / Heating 4: 97 percent / H2 / 5percent Pd/C / ethyl acetate / 2 h / 1034.3 Torr 5: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C 6: pyridine / CH2Cl2 / 3 h / 21 °C 7: Bu3SnH, AIBN / toluene / 5 h / 110 °C 8: 56 percent / benzene / 525 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: pyridine / diethyl ether / 14 h / 0 °C
2: 67 percent / pyridine / CH2Cl2 / 3 h / 21 °C
3: 89 percent / Bu3SnH, AIBN / toluene / 3 h / Heating
4: 97 percent / H2 / 5percent Pd/C / ethyl acetate / 2 h / 1034.3 Torr
5: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C
6: pyridine / CH2Cl2 / 3 h / 21 °C
7: Bu3SnH, AIBN / toluene / 5 h / 110 °C
8: 56 percent / benzene / 525 °C
View Scheme

: (1R)(2R)(7S)(8R)(9S)-3,3,7-Trimethyl-4-hydroxy-8-(acetoxymethyl)tricyclo<5.4.01,7.02,9>undecane

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / CH2Cl2 / 3 h / 21 °C 2: Bu3SnH, AIBN / toluene / 5 h / 110 °C 3: 56 percent / benzene / 525 °C View Scheme

: (1R)(2R)(4R)(7S)(8R)(9S)-3,3,7-Trimethyl-4-methoxy-8-(acetoxymethyl)tricyclo<5.4.01,7.02,9>undecane

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C 2: pyridine / CH2Cl2 / 3 h / 21 °C 3: Bu3SnH, AIBN / toluene / 5 h / 110 °C 4: 56 percent / benzene / 525 °C View Scheme

: (1S)(2R)(5R)(6R)(8R)(9S)(12R)-1,7,7-Trimethyl-6-methoxy-4-oxatetracyclo<7.3.1.02,9>-10-tridecen-3-one

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 92 percent / H2 / 5percent Pd/C / ethyl acetate / 4 h / 1551.4 Torr / Ambient temperature 2: 74 percent / pyridine / diethyl ether / 6 h / 0 °C 3: 0.240 g / pyridine / CH2Cl2 / 21 °C 4: Bu3SnH, AIBN / toluene / 4 h / Heating 5: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C 6: pyridine / CH2Cl2 / 3 h / 21 °C 7: Bu3SnH, AIBN / toluene / 5 h / 110 °C 8: 56 percent / benzene / 525 °C View Scheme
Multi-step reaction with 9 steps 1: LiAlH4 / diethyl ether / 0 deg C to r.t. 2: pyridine / diethyl ether / 14 h / 0 °C 3: 67 percent / pyridine / CH2Cl2 / 3 h / 21 °C 4: 89 percent / Bu3SnH, AIBN / toluene / 3 h / Heating 5: 97 percent / H2 / 5percent Pd/C / ethyl acetate / 2 h / 1034.3 Torr 6: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C 7: pyridine / CH2Cl2 / 3 h / 21 °C 8: Bu3SnH, AIBN / toluene / 5 h / 110 °C 9: 56 percent / benzene / 525 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 92 percent / H2 / 5percent Pd/C / ethyl acetate / 4 h / 1551.4 Torr / Ambient temperature
2: 74 percent / pyridine / diethyl ether / 6 h / 0 °C
3: 0.240 g / pyridine / CH2Cl2 / 21 °C
4: Bu3SnH, AIBN / toluene / 4 h / Heating
5: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C
6: pyridine / CH2Cl2 / 3 h / 21 °C
7: Bu3SnH, AIBN / toluene / 5 h / 110 °C
8: 56 percent / benzene / 525 °C
View Scheme

Multi-step reaction with 9 steps
1: LiAlH4 / diethyl ether / 0 deg C to r.t.
2: pyridine / diethyl ether / 14 h / 0 °C
3: 67 percent / pyridine / CH2Cl2 / 3 h / 21 °C
4: 89 percent / Bu3SnH, AIBN / toluene / 3 h / Heating
5: 97 percent / H2 / 5percent Pd/C / ethyl acetate / 2 h / 1034.3 Torr
6: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C
7: pyridine / CH2Cl2 / 3 h / 21 °C
8: Bu3SnH, AIBN / toluene / 5 h / 110 °C
9: 56 percent / benzene / 525 °C
View Scheme

: (1R)(2R)(4R)(5R)(7S)(8R)(9S)-3,3,7-Trimethyl-4-methoxy-5-hydroxy-8-(acetoxymethyl)tricyclo<5.4.01,7.02,9>undecane

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 0.240 g / pyridine / CH2Cl2 / 21 °C 2: Bu3SnH, AIBN / toluene / 4 h / Heating 3: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C 4: pyridine / CH2Cl2 / 3 h / 21 °C 5: Bu3SnH, AIBN / toluene / 5 h / 110 °C 6: 56 percent / benzene / 525 °C View Scheme

: (1R)(2R)(4R)(7S)(8R)(9S)-3,3,7-Trimethyl-4-methoxy-8-(acetoxymethyl)tricyclo<5.4.01,7.02,9>-10-undecene

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 97 percent / H2 / 5percent Pd/C / ethyl acetate / 2 h / 1034.3 Torr 2: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C 3: pyridine / CH2Cl2 / 3 h / 21 °C 4: Bu3SnH, AIBN / toluene / 5 h / 110 °C 5: 56 percent / benzene / 525 °C View Scheme

: (1R)(2R)(4R)(5R)(7S)(8R)(9S)-3,3,7-Trimethyl-4-methoxy-5-hydroxy-8-(acetoxymethyl)tricyclo<5.4.01,7.02,9>-10-undecene

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 67 percent / pyridine / CH2Cl2 / 3 h / 21 °C 2: 89 percent / Bu3SnH, AIBN / toluene / 3 h / Heating 3: 97 percent / H2 / 5percent Pd/C / ethyl acetate / 2 h / 1034.3 Torr 4: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C 5: pyridine / CH2Cl2 / 3 h / 21 °C 6: Bu3SnH, AIBN / toluene / 5 h / 110 °C 7: 56 percent / benzene / 525 °C View Scheme

: Acetic acid (1S,3aR,4S,7S,8aS,9R)-4,8,8-trimethyl-7-phenoxythiocarbonyloxy-decahydro-1,4-methano-azulen-9-ylmethyl ester

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Bu3SnH, AIBN / toluene / 5 h / 110 °C 2: 56 percent / benzene / 525 °C View Scheme

: Acetic acid (1S,3aR,4S,6R,7R,8aS,9R)-7-methoxy-4,8,8-trimethyl-6-phenoxythiocarbonyloxy-decahydro-1,4-methano-azulen-9-ylmethyl ester

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: Bu3SnH, AIBN / toluene / 4 h / Heating 2: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C 3: pyridine / CH2Cl2 / 3 h / 21 °C 4: Bu3SnH, AIBN / toluene / 5 h / 110 °C 5: 56 percent / benzene / 525 °C View Scheme

: Acetic acid (1S,3aR,4S,6R,7R,8aS,9R)-7-methoxy-4,8,8-trimethyl-6-phenoxythiocarbonyloxy-1,3a,4,5,6,7,8,8a-octahydro-1,4-methano-azulen-9-ylmethyl ester

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 89 percent / Bu3SnH, AIBN / toluene / 3 h / Heating 2: 97 percent / H2 / 5percent Pd/C / ethyl acetate / 2 h / 1034.3 Torr 3: NaI, Me3SiCl, NEt3 / CH2Cl2 / 1 h / 21 °C 4: pyridine / CH2Cl2 / 3 h / 21 °C 5: Bu3SnH, AIBN / toluene / 5 h / 110 °C 6: 56 percent / benzene / 525 °C View Scheme

: 465-24-7
1,4-methanoazulen-9-ol, decahydro-1,5,5,8α-tetramethyl-(1R,3αR,4S,8αS,9S)-

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / PCC, / CH2Cl2 / 3 h / Ambient temperature 2: 92 percent / LiAlH4, / tetrahydrofuran / 3 h / 0 °C 3: 66 percent / MeSO2Cl, DMAP, / pyridine / 16 h / 105 °C View Scheme

: 465-26-9
8-oxolongibornane

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / LiAlH4, / tetrahydrofuran / 3 h / 0 °C 2: 66 percent / MeSO2Cl, DMAP, / pyridine / 16 h / 105 °C View Scheme

: 51830-69-4, 72496-29-8, 107537-54-2
11-hydroxylongicyclene

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / 32percent HBr, acetic acid / 18 h / Ambient temperature 2: silver perchlorate / acetone; H2O / 18 h / Ambient temperature 3: Jones' reagent 4: 55 percent / 85percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating View Scheme

: 91482-03-0, 99529-80-3
8,11-dibromolongibornane

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: silver perchlorate / acetone; H2O / 18 h / Ambient temperature 2: Jones' reagent 3: 55 percent / 85percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating View Scheme

: 99481-27-3
(1S,3aR,4S,8aS)-4,8,8-Trimethyl-9-methylene-decahydro-1,4-methano-azulen-3-ol

: 475-20-7
longifolene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Jones' reagent 2: 55 percent / 85percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating View Scheme

: 475-20-7
longifolene

: 1135-66-6
(-)-isolongifolene

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 35℃; for 8h; Rearrangement;	91%
With β-Zeolite In benzene	74%
With sulfuric acid; acetic acid
With sodium thiosulfate at 100℃; for 0.75h; Reagent/catalyst; Temperature; Sonication;

: 475-20-7
longifolene

: (1S,3aR,4S,8aR,9S)-1,2,3,3a,4,5,6,7,8,8a-decahydro-4,8,8-trimethylspiro[1,4-methanoazulene-9,2'-oxirane]

Conditions

Conditions	Yield
With ozone In acetone at -80℃;	91%

: 475-20-7
longifolene

A: 1135-66-6
(-)-isolongifolene

B: 87064-18-4
(-)-alloisolongifolene

Conditions

Conditions	Yield
chloroacetic acid for 24h; Heating;	A 90% B 10%
bromoacetic acid for 24h; Heating; or ICH2COOH;	A 15% B 85%
bromoacetic acid for 24h; Heating; also with ICH2COOH or ClCH2COOH;	A 25% B 85%
With aluminum oxide; sodium at 180℃;	A 62% B 28%

: 475-20-7
longifolene

: 3,3,7-trimethyl tricyclo<5.4.0.0> undecan-8-carboxylic acid

Conditions

Conditions	Yield
With cobalt; oxygen; isobutyraldehyde In acetonitrile for 37h;	65%

: 475-20-7
longifolene

: N-(tert-butyl)-N-((ethoxycarbonothioyl)thio)-3,5-bis(trifluoromethyl)benzamide

: O-ethyl S-[(1S,3aR,4S,6S,8aS)-4,8,8-trimethyl-9-methylenedecahydro-1,4-methanoazulen-6-yl]carbonodithioate

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; Irradiation; Inert atmosphere; diastereoselective reaction;	54%

: 475-20-7
longifolene

: 8-epoxy-3,3,7-trimethyltricyclo<5.4.0.0>undecane

Conditions

Conditions	Yield
With oxygen; isobutyraldehyde; cobalt dichloride In acetonitrile at 25℃;	52%
With cobalt dichloride; oxygen; isobutyraldehyde In acetonitrile for 15h;	51%

: 475-20-7
longifolene

: 487-74-1
(1S,3aR,4S,8aS,9S)-decahydro-4,8,8-trimethyl-1,4-methanoazulen-9-carboxylic acid

Conditions

Conditions	Yield
With oxygen; isobutyraldehyde; (MeO2CCH(Bn)N=CH(C6H4O)-o)2Co In acetonitrile at 25℃;	51%
Multi-step reaction with 2 steps 1: (i) CrO3, (ii) /BRN= 102415/ 2: KOH / methanol View Scheme
Multi-step reaction with 4 steps 1: Heating; Irradiation 2: (i) KOCH2tBu, (ii) aq. KMnO4 3: LiAlH4 / diethyl ether / Heating 4: (i) Al2O3, benzene, (ii) O2, Et2O View Scheme

: 475-20-7
longifolene

: 25491-00-3
(1R,2S,7S,8S,9S)-3,3,7-trimethyltricyclo[5.4.0.02,9]undecane-8-carbaldehyde

Conditions

Conditions	Yield
With ozone In dichloromethane at -80 - 20℃; for 840000h;	51%
Multi-step reaction with 4 steps 1: Heating; Irradiation 2: (i) KOCH2tBu, (ii) aq. KMnO4 3: LiAlH4 / diethyl ether / Heating 4: Al2O3 / benzene View Scheme

: 475-20-7
longifolene

: 108-24-7
acetic anhydride

A: 61262-69-9
Longibornan-9-ol-acetat

B: 1135-66-6
(-)-isolongifolene

C: 3338-56-5
ω-acetyllongifolene

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate for 0.5h; Product distribution; Mechanism; other terpenes and reagents;	A 2% B 50% C 24%
With boron trifluoride diethyl etherate for 0.5h; ice bath;	A 2% B 50% C 24%

...Expand

: 475-20-7
longifolene

: 116403-51-1
(-)-longicamphenylone

Conditions

Conditions	Yield
With potassium permanganate; adogen 464 In dichloromethane; acetic acid for 48h; Ambient temperature;	45%
With Perbenzoic acid; chloroform
With chromium(VI) oxide; acetic acid
With chromium(VI) oxide In acetic acid
Multi-step reaction with 2 steps 1: PhCO3H / CHCl3; ethanol 2: PhCO3H / CHCl3; ethanol View Scheme

: 475-20-7
longifolene

A: 116403-51-1
(-)-longicamphenylone

B: 3,3,7-trimethyl tricyclo<5.4.0.0> undecan-8-carboxylic acid

Conditions

Conditions	Yield
With potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; acetic acid for 48h; Ambient temperature;	A 42% B 22%
With potassium permanganate In dichloromethane; acetic acid Ambient temperature;	A 10% B 26%

: 475-20-7
longifolene

A: 487-73-0
(1S,3aR,4S,8aS,9R)-decahydro-4,8,8-trimethyl-1,4-methanoazulen-9-carboxylic acid

B: 487-74-1
(1S,3aR,4S,8aS,9S)-decahydro-4,8,8-trimethyl-1,4-methanoazulen-9-carboxylic acid

C: 474-96-4, 4439-95-6, 140223-97-8
longidione

D: 116403-51-1
(-)-longicamphenylone

Conditions

Conditions	Yield
With ruthenium(II) chloride; sodium periodate In chloroform; water; acetonitrile for 8h; Ambient temperature; Yield given. Title compound not separated from byproducts;	A n/a B n/a C 5.5% D 36%
With ruthenium(II) chloride; sodium periodate In chloroform; water; acetonitrile for 8h; Ambient temperature;	A n/a B n/a C 5.5% D 36%

...Expand

: 475-20-7
longifolene

: 1137-12-8, 41437-68-7
(+)-Longicyclen

Conditions

Conditions	Yield
With aluminum oxide; sodium at 110℃;	28%

: 475-20-7
longifolene

: 108-24-7
acetic anhydride

A: 124024-34-6
7-endo-N-acetyl-13-longifolanamide

B: 124024-33-5
7-endo-13,13-diacetoxylongifolane

C: 124024-35-7
13-acetoxy-7-exo-acetamidolongifolane

Conditions

Conditions	Yield
With hexaaquairon(II) perchlorate; dihydrogen peroxide In acetonitrile at 30℃; for 0.0833333h;	A 3.6% B 27.1% C 21.2%
With hexaaquairon(II) perchlorate; dihydrogen peroxide In acetonitrile at 30℃; for 0.0833333h;	A 3.6% B 27.1% C 21.2%

...Expand

: 475-20-7
longifolene

A: 487-73-0
(1S,3aR,4S,8aS,9R)-decahydro-4,8,8-trimethyl-1,4-methanoazulen-9-carboxylic acid

B: 116403-51-1
(-)-longicamphenylone

C: (1S,3aR,4S,8aR,9S)-1,2,3,3a,4,5,6,7,8,8a-decahydro-4,8,8-trimethylspiro[1,4-methanoazulene-9,2'-oxirane]

D: (E)-[(1S,3aR,4S,8aR)-decahydro-4,8,8-trimethyl-1,4-methanoazulen-9-ylidene]methanol

Conditions

Conditions	Yield
With potassium permanganate; Aliquat 336 In dichloromethane Further byproducts given;	A n/a B 22% C n/a D n/a

...Expand

: 475-20-7
longifolene

: 108-24-7
acetic anhydride

A: 61262-69-9
Longibornan-9-ol-acetat

B: 1135-66-6
(-)-isolongifolene

C: 59056-72-3
1-(octahydro-7,7,8,8-tetramethyl-2,3b-methano-3bH-cyclopenta[1,3]cyclopropa[1,2]benzen-4-yl)ethanone

D: 3338-56-5
ω-acetyllongifolene

Conditions

Conditions	Yield
With tin(IV) chloride for 0.5h; ice bath; Yields of byproduct given;	A n/a B 1.77 g C 11% D n/a

...Expand

: 56-23-5
tetrachloromethane

: 110-22-5
diacetyl peroxide

: 475-20-7
longifolene

: 2615-47-6, 94669-77-9
(3S,7S)-3-chloro-15-trichloromethyl-longifolane

...Expand

: 475-20-7
longifolene

: (7Ξ)-longifolane-7,15-diol

Conditions

Conditions	Yield
With osmium(VIII) oxide; diethyl ether

: 475-20-7
longifolene

: 1139-53-3, 140223-99-0
(1R)-2,2,5a-trimethyl-(5at,10at)-decahydro-1r,8-cyclo-heptalen-7-one

Conditions

Conditions	Yield
With lead(IV) acetate; acetic acid anschl. mit aethanol. NaOH;

: 186581-53-3, 908094-01-9
diazomethane

: 475-20-7
longifolene

A: 13928-57-9, 99032-59-4
(7R)-longifolanoic acid-(15)-methyl ester

B: 13928-57-9, 99032-59-4
(7S)-longifolanoic acid-(15)-methyl ester

Conditions

Conditions	Yield
(i) CrO3, (ii) /BRN= 102415/; Multistep reaction;

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 475-20-7
longifolene

: C19H30O2

Conditions

Conditions	Yield
With copper

: 67-56-1
methanol

: 475-20-7
longifolene

: 13928-57-9, 99032-59-4
(7S)-longifolanoic acid-(15)-methyl ester

Conditions

Conditions	Yield
(i) CrO3, aq. H2SO4, AcOH, (ii) /BRN= 1098229/, benzene; Multistep reaction;

: 56-23-5
tetrachloromethane

: 475-20-7
longifolene

: 2615-47-6, 94669-77-9
(3S,7S)-3-chloro-15-trichloromethyl-longifolane

Conditions

Conditions	Yield
With diacetyl peroxide

: 1189-71-5
isocyanate de chlorosulfonyle

: 475-20-7
longifolene

: C16H24ClNO3S

Conditions

Conditions	Yield
In diethyl ether

(+)-Longifolene Chemical Properties

Molecule structure of d-Longifolene (CAS NO.475-20-7):

Molecular Weight: 204.35106 g/mol
Molecular Formula: C₁₅H₂₄
Density: 0.93 g/cm³
Boiling Point: 252.2 °C at 760 mmHg
Flash Point: 102.2 °C
Index of Refraction: 1.508
Molar Refractivity: 64.85 cm³
Molar Volume: 217.4 cm³
Polarizability: 25.71×10^-24 cm³
Surface Tension: 31.2 dyne/cm
Enthalpy of Vaporization: 46.97 kJ/mol
Vapour Pressure: 0.0312 mmHg at 25 °C
Storage Temp.: 2-8 °C
XLogP3-AA: 5.1
Exact Mass: 204.187801
MonoIsotopic Mass: 204.187801
Heavy Atom Count: 15
Complexity: 312
Canonical SMILES: CC1(CCCC2(C3C1C(C2=C)CC3)C)C
InChI: InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3
InChIKey: PDSNLYSELAIEBU-UHFFFAOYSA-N
EINECS: 207-491-2
Product Categories of d-Longifolene (CAS NO.475-20-7): Pharmaceutical Raw Materials

(+)-Longifolene Uses

d-Longifolene (475-20-7) is used in the manufacture or preparation of Flavor.

(+)-Longifolene Toxicity Data With Reference

1.		orl-rat LD50:>5 g/kg		FCTOD7 Food and Chemical Toxicology. 30 (1992),67S.
2.		skn-rbt LD50:>5 g/kg		FCTOD7 Food and Chemical Toxicology. 30 (1992),67S.

(+)-Longifolene Consensus Reports

Reported in EPA TSCA Inventory.

(+)-Longifolene Safety Profile

WGK Germany: 2
RTECS: PB7724500
F: 8-10-23
Low toxicity by ingestion and skin contact. When heated to decomposition it emits acrid smoke and irritating vapors.

(+)-Longifolene Specification

d-Longifolene (CAS NO.475-20-7) is also named as 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene- ; 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-, (1S-(1alpha,3abeta,4alpha,8abeta)) ; Junipen ; Junipene ; Kuromatsuen ; Kuromatsuene ; Longifolen ; Longifolene ; NSC 150808 .

Product Name

(+)-Longifolene

Synthetic route

(+)-Longifolene Chemical Properties

(+)-Longifolene Uses

(+)-Longifolene Toxicity Data With Reference

(+)-Longifolene Consensus Reports

(+)-Longifolene Safety Profile

(+)-Longifolene Specification

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