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4674-50-4

Basic Information
CAS No.: 4674-50-4
Name: 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-
Article Data: 45
Cas Database
Molecular Structure:
Molecular Structure of 4674-50-4 (2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-)
Formula: C15H22O
Molecular Weight: 218.339
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;
EINECS: 225-124-4
Density: 0.96 g/cm3
Melting Point: 36-37 °C
Boiling Point: 318.6 °C at 760 mmHg
Flash Point: 142.1 °C
Solubility: Slightly soluble in ethanol and chloroform. Partly soluble in water.
Appearance: colourless crystal
Hazard Symbols: N/A
Risk Codes: N/A
Safety: 23-24/25
Transport Information: N/A
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
ConditionsYield
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;
563-41-7

semicarbazide hydrochloride

4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
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%
Conditions
ConditionsYield
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%

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
ConditionsYield
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%
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
ConditionsYield
With lyophilisate of Pleurotus sapidus In aq. buffer at 20℃; for 48h; pH=7.4; Enzymatic reaction;A 16%
B 7%
Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With aluminum oxide In hexane at 60℃; for 24h;

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
ConditionsYield
Mechanism; Product distribution; multistep reaction: photooxygenation + reduction; reaction with triplet and singlet oxygen;
67779-29-7

2-Methyl-4-isopropenyl-6-n-butylthiomethylen-cyclohexanon

3102-33-8

trans-3-penten-2-one

4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
(i) KOtBu, tBuOH, (ii) aq. KOH; Multistep reaction;
Downstream Products
15764-04-2
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    4674-50-4

    4674-50-4 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-

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

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    4674-50-4

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

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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: 26.44×10-24 cm3; (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