2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)- supplier

Name
NOOTKATONE
EINECS 225-124-4
CAS No. 4674-50-4
Article Data45
CAS DataBase
Density 0.96 g/cm³
Solubility Slightly soluble in ethanol and chloroform. Partly soluble in water.
Melting Point 36-37 °C
Formula C₁₅H₂₂O
Boiling Point 318.6 °C at 760 mmHg
Molecular Weight 218.339
Flash Point 142.1 °C
Transport Information
Appearance colourless crystal
Safety 23-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one;(4R,4aS,6R)-4,4a-Dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one;
PSA 17.07000
LogP 3.90420

Synthetic route

: 72453-44-2
(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With sodium acetate In water; acetic acid at 100℃; for 2h;	93%
With sodium acetate; acetic acid at 100℃; for 2h; Inert atmosphere;	93%
With sodium acetate; acetic acid at 100℃; for 2h;	93%
With aluminum oxide In hexane at 60℃; for 24h; Yield given;

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

: 563-41-7
semicarbazide hydrochloride

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Stage #1: valencene With manganese(IV) oxide In dichloromethane at -25℃; for 0.5h; Stage #2: With tert.-butylhydroperoxide In dichloromethane; water at -10℃; for 9h; Reflux; Stage #3: semicarbazide hydrochloride Further stages;	83%

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With Czapek-pepton medium; Pallavicinia subcilita at 30℃; for 168h; pH=7.0;	82%
With pyridine; tert.-butylhydroperoxide; N-hydroxy-3,4,5,6-tetrachlorophthalimide; lithium perchlorate In acetone Reagent/catalyst; Solvent; Electrochemical reaction; chemoselective reaction;	77%
With tert.-butylhydroperoxide; sodium chlorite In water; acetonitrile at 50℃; for 18h; Product distribution / selectivity;	72%

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

A: 136918-14-4
phthalimide

B: 4674-50-4
(+)-nootkatone

C: 840474-83-1
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol

Conditions

Conditions	Yield
With oxygen; N-hydroxyphthalimide; cobalt nitrate; cobalt(II) acetate; cobalt(III) acetylacetonate In acetonitrile at 40℃; under 9750.98 Torr; for 3h; Product distribution / selectivity;	A n/a B 67.9% C 5.6%
With oxygen; N-hydroxyphthalimide; cobalt(II) acetate; cobalt(III) acetylacetonate In acetonitrile at 40℃; under 9750.98 Torr; for 4h; Product distribution / selectivity;	A n/a B 53.7% C 1.4%

...Expand

: 329309-57-1
(4R,4aS,6R)-2-hydroperoxy-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalene

A: 4674-50-4
(+)-nootkatone

B: 840474-83-1
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol

Conditions

Conditions	Yield
With lyophilisate of Pleurotus sapidus In aq. buffer at 20℃; for 48h; pH=7.4; Enzymatic reaction;	A 16% B 7%

: 17334-55-3
β-gurjunene

A: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

B: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With culture medium of Mucor species; Czapek-pepton medium at 30℃; for 168h;	A 0.7% B 0.6%

: 20489-50-3
(4R,6R,10S)-4,10-dimethyl-6-(1‘-hydroxyisopropyl)-1-en-3,4,5,6,7,8-hexahydronaphthalen-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With pyridine; trichlorophosphate

: 72453-44-2
(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

A: 15764-04-2
(4R,4aS)-(+)-4,4a-dimethyl-6-isopropylidene-4,4a,5,6,7,8-hexahydro-(3H)-naphthalen-2-one

B: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With aluminum oxide In hexane at 60℃; for 24h;

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

A: 50763-63-8
(2R,4aR,8R,8aS)-2-Isopropenyl-8,8a-dimethyl-1,3,4,7,8,8a-hexahydro-2H-naphthalen-4a-ol

B: 50763-66-1
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol

C: 50763-67-2
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

D: 4674-50-4
(+)-nootkatone

E: 32420-34-1, 32420-35-2, 50763-64-9, 50763-65-0, 53643-08-6
(4R,4aS,6R)-6-Isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ol

Conditions

Conditions	Yield
Mechanism; Product distribution; multistep reaction: photooxygenation + reduction; reaction with triplet and singlet oxygen;

...Expand

: 67779-29-7
2-Methyl-4-isopropenyl-6-n-butylthiomethylen-cyclohexanon

: 3102-33-8
trans-3-penten-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
(i) KOtBu, tBuOH, (ii) aq. KOH; Multistep reaction;

: 75-91-2
tert.-butylhydroperoxide

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

A: 4674-50-4
(+)-nootkatone

B: 2β-t-butylperoxy-4α,5α,7β-eremophila-1(10),11-diene

C: 9β-t-butylperoxy-2-oxo-4α,5α,7β-eremophila-1(10),11-diene

Conditions

Conditions	Yield
With copper(l) iodide In acetonitrile at 50℃; for 18h; Substitution; oxydation;	A 260 mg B 31 mg C n/a

...Expand

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

A: 50763-67-2
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

B: 4674-50-4
(+)-nootkatone

C: (-)-2-(2R)-(1,2,3,4,6,7,8,8a-octahydro-8α,8aβ-dimethyl-2α-naphthalenyl)-2-propen-1-ol

Conditions

Conditions	Yield
With chicory; enzymes from roots of Cichorium intybus L; NADPH In ethanol for 1h; pH=7.5; Product distribution; Further Variations:; Reagents;

...Expand

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

A: (+)-(4R,5S,7R,11S)-11,12-epoksynootkatone

B: 50763-66-1
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol

C: 4674-50-4
(+)-nootkatone

D: (1aR,4R,4aS,6R,8aS)-4,4a-dimethyl-6-(prop-1-en-2-yl)octahydro-1aH-naphtho[1,8a-b]oxirene

Conditions

Conditions	Yield
With 1,4-dihydronicotinamide adenine dinucleotide; cytochrome P450BM-3 Product distribution; Enzyme kinetics; Further Variations:; Reagents;

...Expand

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

A: 50763-67-2
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

B: 4674-50-4
(+)-nootkatone

C: 226546-99-2
9α-hydroxy-2-oxo-4α,5α,7β-eremophila-1(10),11-diene

Conditions

Conditions	Yield
With 1,4-dihydronicotinamide adenine dinucleotide; cytochrome P450cam In ethanol Product distribution; Enzyme kinetics; Further Variations:; Reagents;

...Expand

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

A: 50763-66-1
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol

B: 50763-67-2
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

C: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With Botryosphaeria dothidea (Ume BD8398II); Czapek-pepton medium at 30℃; for 168h; pH=7.0;	A 31 % Chromat. B 18 % Chromat. C 43 % Chromat.

...Expand

: 50763-66-1
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With Chlorella pyrenoidosa for 24h;

: 50763-67-2
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With Chlorella fusca for 24h;
Multi-step reaction with 2 steps 1: 42 percent / p-nitrobenzoic acid; triphenylphosphine; diethyl azodicarboxylate 2: Chlorella pyrenoidosa / 24 h View Scheme

: 38651-65-9
(1R,5S)-(+)-nopinone

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 88 percent / triethylamine / dimethylformamide / 24 h / 95 °C 2: 96 percent / TiCl4 / CH2Cl2 / 1.5 h / -78 °C 3: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 4: 81 percent / TiCl4 / CH2Cl2 5: 71 percent / NaNH2 / benzene 6: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight. 7: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 8: Al2O3 / hexane / 24 h / 60 °C View Scheme
Multi-step reaction with 8 steps 1: 88 percent / triethylamine / dimethylformamide / 24 h / 95 °C 2: 96 percent / TiCl4 / CH2Cl2 / 1.5 h / -78 °C 3: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 4: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C 5: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h. 6: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour. 7: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 8: Al2O3 / hexane / 24 h / 60 °C View Scheme
Multi-step reaction with 7 steps 1: 55 percent / N-methylaniline, EtMgBr / benzene; diethyl ether / 1 h / 0 °C 2: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 81 percent / TiCl4 / CH2Cl2 4: 71 percent / NaNH2 / benzene 5: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight. 6: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 7: Al2O3 / hexane / 24 h / 60 °C View Scheme

: 72453-41-9
(1R,3S,5R)-3-<(1R)-1-Methyl-3-oxobutyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 2: Al2O3 / hexane / 24 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid; hydrogenchloride / 21 h / 20 °C / Inert atmosphere 2: acetic acid; sodium acetate / 2 h / 100 °C View Scheme

: 72453-38-4, 72541-05-0, 73068-69-6
(1R,3R,5R)-6,6-Dimethyl-3-(1-hydroxyethyl)bicyclo<3.1.1>heptan-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 2: 81 percent / TiCl4 / CH2Cl2 3: 71 percent / NaNH2 / benzene 4: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight. 5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 6: Al2O3 / hexane / 24 h / 60 °C View Scheme
Multi-step reaction with 6 steps 1: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 2: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C 3: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h. 4: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour. 5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 6: Al2O3 / hexane / 24 h / 60 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
2: 81 percent / TiCl4 / CH2Cl2
3: 71 percent / NaNH2 / benzene
4: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
6: Al2O3 / hexane / 24 h / 60 °C
View Scheme

Multi-step reaction with 6 steps
1: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
2: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C
3: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h.
4: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour.
5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
6: Al2O3 / hexane / 24 h / 60 °C
View Scheme

: 72453-33-9
(1R,5R)-6,6-Dimethyl-2-<(trimethylsilyl)oxy>bicyclo<3.1.1>hept-2-ene

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 96 percent / TiCl4 / CH2Cl2 / 1.5 h / -78 °C 2: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 81 percent / TiCl4 / CH2Cl2 4: 71 percent / NaNH2 / benzene 5: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight. 6: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 7: Al2O3 / hexane / 24 h / 60 °C View Scheme
Multi-step reaction with 7 steps 1: 96 percent / TiCl4 / CH2Cl2 / 1.5 h / -78 °C 2: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C 4: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h. 5: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour. 6: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 7: Al2O3 / hexane / 24 h / 60 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 96 percent / TiCl4 / CH2Cl2 / 1.5 h / -78 °C
2: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
3: 81 percent / TiCl4 / CH2Cl2
4: 71 percent / NaNH2 / benzene
5: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
6: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
7: Al2O3 / hexane / 24 h / 60 °C
View Scheme

Multi-step reaction with 7 steps
1: 96 percent / TiCl4 / CH2Cl2 / 1.5 h / -78 °C
2: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
3: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C
4: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h.
5: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour.
6: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
7: Al2O3 / hexane / 24 h / 60 °C
View Scheme

: 72453-39-5, 72541-06-1, 73068-72-1, 73068-73-2, 75657-63-5
(1R,3S,5S)-6,6-Dimethyl-3-<1-methyl-3-butenyl>bicyclo<3.1.1>heptan-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h. 2: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour. 3: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 4: Al2O3 / hexane / 24 h / 60 °C View Scheme

: 72453-42-0, 72541-07-2, 73068-70-9, 73068-71-0, 75657-65-7
(1R,3S,5S)-6,6-Dimethyl-3-<1-methyl-3-methyl-3-butenyl>bicyclo<3.1.1.>heptan-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 71 percent / NaNH2 / benzene 2: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight. 3: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 4: Al2O3 / hexane / 24 h / 60 °C View Scheme

: 72453-40-8, 72521-66-5, 75657-64-6
(1R,3S,5R)-3-<1-Methyl-3-butenyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour. 2: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 3: Al2O3 / hexane / 24 h / 60 °C View Scheme

: 72453-43-1, 72541-08-3, 75657-66-8
(1R,3S,5R)-3-<1-Methyl-3-methyl-3-butenyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight. 2: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 3: Al2O3 / hexane / 24 h / 60 °C View Scheme

: 73068-31-2
(1R,5R)-6,6-Dimethyl-3-(Z)-ethylidenebicyclo<3.1.1>heptan-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: p-toluenesulfonic acid monohydrate / ethanol / 3 h / Ambient temperature 2: 81 percent / TiCl4 / CH2Cl2 3: 71 percent / NaNH2 / benzene 4: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight. 5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 6: Al2O3 / hexane / 24 h / 60 °C View Scheme
Multi-step reaction with 6 steps 1: p-toluenesulfonic acid monohydrate / ethanol / 3 h / Ambient temperature 2: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C 3: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h. 4: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour. 5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 6: Al2O3 / hexane / 24 h / 60 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: p-toluenesulfonic acid monohydrate / ethanol / 3 h / Ambient temperature
2: 81 percent / TiCl4 / CH2Cl2
3: 71 percent / NaNH2 / benzene
4: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
6: Al2O3 / hexane / 24 h / 60 °C
View Scheme

Multi-step reaction with 6 steps
1: p-toluenesulfonic acid monohydrate / ethanol / 3 h / Ambient temperature
2: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C
3: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h.
4: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour.
5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
6: Al2O3 / hexane / 24 h / 60 °C
View Scheme

: 72453-37-3
(1R,5R)-6,6-Dimethyl-3-(E)-ethylidenebicyclo<3.1.1>heptan-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 81 percent / TiCl4 / CH2Cl2 2: 71 percent / NaNH2 / benzene 3: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight. 4: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 5: Al2O3 / hexane / 24 h / 60 °C View Scheme
Multi-step reaction with 5 steps 1: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C 2: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h. 3: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour. 4: 73 percent / HCl / acetic acid / 21 h / Ambient temperature 5: Al2O3 / hexane / 24 h / 60 °C View Scheme
Multi-step reaction with 6 steps 1.1: magnesium / tetrahydrofuran / 0.5 h / Reflux 1.2: -78 °C 2.1: potassium hydride; 18-crown-6 ether / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere 3.1: sodium amide / benzene / 5 h / Inert atmosphere; Reflux 3.2: 17.5 h / 45 °C 4.1: acetic acid; zinc / dichloromethane / 5 h / -78 - 30 °C / Inert atmosphere 5.1: acetic acid; hydrogenchloride / 21 h / 20 °C / Inert atmosphere 6.1: acetic acid; sodium acetate / 2 h / 100 °C View Scheme

: 67779-36-6
2-Methyl-4-isopropenyl-6-hydroxymethylen-cyclohexanon

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: TsOH 2: (i) KOtBu, tBuOH, (ii) aq. KOH View Scheme

: 118710-90-0
(+)-(2R,4R)-2-methyl-4-isopropenylcyclohexanone

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOMe, MeOH 2: TsOH 3: (i) KOtBu, tBuOH, (ii) aq. KOH View Scheme

: 4674-50-4
(+)-nootkatone

: 840474-83-1
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃; for 4.33333h; Time;	98.3%

: 4674-50-4
(+)-nootkatone

: 5195-69-7
6-isopropyl-4,4a-dimethyl-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-one

Conditions

Conditions	Yield
With Wilkinson's catalyst; hydrogen In benzene at 20℃; for 8h;	96%
With Wilkinson's catalyst; hydrogen In benzene for 14h; Ambient temperature;	81%
With Wilkinson's catalyst; hydrogen In benzene for 14h; Ambient temperature;	81%
With tris(triphenylphosphine)rhodium(l) chloride; hydrogen In benzene for 8h;
With Wilkinson's catalyst; hydrogen under 5250.53 Torr; for 2h;

: 4674-50-4
(+)-nootkatone

: 439112-90-0
6-isopropenyl-4,4a-dimethyl-3,4,5,6,7,8-hexahydro-1aH-naphtho[1,8a-b]oxiren-2-one

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide	96%

: 4674-50-4
(+)-nootkatone

: 14281-94-8, 32661-49-7, 32661-50-0
lithium tetramethyl alanate

: (4R,4aS,6R)-6-Isopropenyl-2,4,4a-trimethyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-2-ol

Conditions

Conditions	Yield
copper(I) bromide In tetrahydrofuran; diethyl ether 0.5 h at 0 deg C, 6 h at room temp.;	94%

: 4674-50-4
(+)-nootkatone

: 4301-14-8
acetylenemagnesium bromide

: 1449115-27-8
(3R,4aS,5R)-7-ethynyl-4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5-hexahydronaphthalene

Conditions

Conditions	Yield
Stage #1: (+)-nootkatone With N,N-phenylbistrifluoromethane-sulfonimide; lithium hexamethyldisilazane at -78℃; Inert atmosphere; Stage #2: acetylenemagnesium bromide With tetrakis(triphenylphosphine) palladium(0) at 20℃; Inert atmosphere;	94%

: 4674-50-4
(+)-nootkatone

: fluoro-(+)-nootkatone

Conditions

Conditions	Yield
With HO4S(1-)K(1+)13FH In 1,2-dichloro-ethane at 0 - 20℃; for 2h; regioselective reaction;	94%

: 4674-50-4
(+)-nootkatone

: 51557-49-4
(+)-cis-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2-(3H)-naphthalenone

Conditions

Conditions	Yield
Stage #1: (+)-nootkatone With methanol; ozone Stage #2: With ferrous(II) sulfate heptahydrate; thiophenol at -78 - 20℃; for 0.5h;	94%

: 4674-50-4
(+)-nootkatone

: 50763-67-2
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

Conditions

Conditions	Yield
With sodium tetrahydroborate; cerium(III) chloride heptahydrate In methanol at 23℃; for 0.166667h; Inert atmosphere;	91%
With sodium tetrahydroborate; cerium(III) chloride	87%
With sodium tetrahydroborate; cerium(III) chloride In ethanol at 20℃; for 1h;	82.7%

: 4674-50-4
(+)-nootkatone

: C15H22Cl2

Conditions

Conditions	Yield
With C26H24Cl2P2(2+)CH2Cl22C2H4Cl2*Cl5Sb(2-); water In nitromethane at 23℃; for 16h; Inert atmosphere;	91%

: 75-24-1
trimethylaluminum

: 4674-50-4
(+)-nootkatone

A: (3R,4aS,5R)-3-Isopropenyl-4a,5,7-trimethyl-1,2,3,4,4a,5-hexahydro-naphthalene

B: (4R,4aS,6R)-6-Isopropenyl-4,4a,8a-trimethyl-octahydro-naphthalen-2-one

Conditions

Conditions	Yield
copper(I) bromide In tetrahydrofuran for 22h; Ambient temperature;	A 90% B 2%
bis(acetylacetonate)nickel(II) In tetrahydrofuran for 4.5h; Ambient temperature;	A 17% B 77%

...Expand

: 4674-50-4
(+)-nootkatone

: 4301-14-8
acetylenemagnesium bromide

Conditions

Conditions	Yield
Stage #1: (+)-nootkatone With 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride at 20℃; Inert atmosphere; Stage #2: acetylenemagnesium bromide With tetrakis(triphenylphosphine) palladium(0) at 20℃; Inert atmosphere;	88%

2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)- Specification

The 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-, with the CAS registry number 4674-50-4, is also known as (4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one. It belongs to the product categories of Chiral Building Blocks; Ketones; Organic Building Blocks. Its EINECS registry number is 225-124-4. The molecular formula of this chemical is C₁₅H₂₂O and molecular weight is 218.3346. What's more, its IUPAC name is (4R,4aS,6R)-4,4a-Dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one. In addition, it should be stored in condition of cold, dry and inclosed. And it is stable in condition of normal temperature and pressure. It is colourless crystal. When you are dealing with this chemical, you should be very careful. Avoid contacting with skin and eyes. Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer).

Physical properties about 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-e are: (1)ACD/LogP: 3.84; (2)#of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.84; (4)ACD/LogD (pH 7.4): 3.84; (5)ACD/BCF (pH 5.5): 487.98; (6)ACD/BCF (pH 7.4): 487.98; (7)ACD/KOC (pH 5.5): 2923.88; (8)ACD/KOC (pH 7.4): 2923.88; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 17.07 Å²; (13)Index of Refraction: 1.503; (14)Molar Refractivity: 66.71 cm³; (15)Molar Volume: 225.4 cm³; (16)Polarizability: 26.44×10^-24cm³; (17)Surface Tension: 32.5 dyne/cm; (18)Density: 0.96 g/cm³; (19)Flash Point: 142.1 °C; (20)Enthalpy of Vaporization: 56.01 kJ/mol; (21)Boiling Point: 318.6 °C at 760 mmHg; (22)Vapour Pressure: 0.000358 mmHg at 25 °C; (23) Melting Point: 36-37 °C; (24)Fp: 99 °C; (25)Refractive index: n20/D 1.52.

Preparation of 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-: this chemical can be prepared by (+-)-Valencen. This reaction needs reagent CrO₃*(Pyridine)₂ and solvent CH₂Cl₂. The reaction time is 12 hours. The yield is 80%.

2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)- can be prepared by (+-)-Valencen.

Use of 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-: it can react with 1,2-Ethanedithiobis(trimethylsilane) to give C₁₇H₂₆S₂.The reaction occurs with reagent ZnI₂ and solvent Diethyl ether. This reaction time is 14 hours. The yield is 93 %.

2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)- can react with 1,2-Ethanedithiobis(trimethylsilane) to give C17H26S2.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C2\C=C1\CC[C@@H](\C(=C)C)C[C@@]1(C)[C@H](C)C2
(2) InChI: InChI=1/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1
(3) InChIKey: WTOYNNBCKUYIKC-JMSVASOKBQ

Product Name

NOOTKATONE

Synthetic route

2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)- Specification

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