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Basic Information
CAS No.: 13215-88-8
Name: Tabanone
Article Data: 5
Molecular Structure:
Molecular Structure of 13215-88-8 (Tabanone)
Formula: C13H18O
Molecular Weight: 190.285
Synonyms: 2-Cyclohexen-1-one,4-(2-butenylidene)-3,5,5-trimethyl- (7CI,8CI,9CI);Megastigmatrienone;4-(But-2-en-1-ylidene)-3,5,5-trimethylcyclohex-2-en-1-one;
EINECS: 236-187-2
Density: 0.968 g/cm3
Boiling Point: 289.203 °C at 760 mmHg
Flash Point: 124.784 °C
Solubility: 361mg/L at 20℃
PSA: 17.07000
LogP: 3.43420
Synthetic route
127-51-5

3-methyl-4-(2,6,6-trimethylcyclohex-2-enyl)-but-3-en-2-one

13215-88-8

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

Conditions
ConditionsYield
Stage #1: 3-methyl-4-(2,6,6-trimethylcyclohex-2-enyl)-but-3-en-2-one With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In acetone at 30 - 35℃; for 4h;
Stage #2: With potassium borohydride In ethanol at 25℃;
52.7%
896107-70-3

9-hydroxymegastigma-4,7-dien-3-one

A

78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

B

20547-99-3

2,6,6-trimethyl-1,4-cyclohexanedione

C

1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

D

13215-88-8

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

E

megastigmatrienone

Conditions
ConditionsYield
In water Heating; pH=1;

3,4-Dehydro-3-phenylthio-β-ionol

13215-88-8

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

Conditions
ConditionsYield
With hydrogenchloride for 0.5h; Ambient temperature; Yield given;
149457-34-1

6-Bromo-8-but-3-enyl-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-7-ene

A

13215-88-8

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

B

38818-55-2

4-<(E)-Buta-1,3-dienyl>-3,5,5-trimethylcyclohex-2-enone

C

4-(But-3-enylidene)-3,5,5-trimethylcyclohex-2-enone

Conditions
ConditionsYield
With hydrogenchloride; 1,8-diazabicyclo[5.4.0]undec-7-ene 1.) toluene, reflux, 5 h, 2.) THF, 25 deg C, 5 h; Yield given. Multistep reaction. Yields of byproduct given;
14203-64-6

7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one

13215-88-8

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / Li / tetrahydrofuran / 1.) 10-15 deg C, 2.) r.t., 1 h
2: 80 percent / PBr3, pyridine / toluene / 1 h / -10 °C
3: 1.) DBU, 2.) 1 M aq. HCl / 1.) toluene, reflux, 5 h, 2.) THF, 25 deg C, 5 h
View Scheme
149457-31-8

8-(But-3-enyl)-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-ol

13215-88-8

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / PBr3, pyridine / toluene / 1 h / -10 °C
2: 1.) DBU, 2.) 1 M aq. HCl / 1.) toluene, reflux, 5 h, 2.) THF, 25 deg C, 5 h
View Scheme
14398-35-7

(3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one

13215-88-8

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: CH3COOH / ethanol / 2 h / 40 °C
2: 2.) DBU / 1.) CH2Cl2, -30 deg C, 15 min, 2.) 0 deg C to r.t., 1 h
3: CH2O / tetrahydrofuran; H2O / 1 h / Ambient temperature
4: NaBH4 / methanol / 0.5 h / 0 °C
5: 2 N HCl / 0.5 h / Ambient temperature
View Scheme

(E)-4-(2,6,6-Trimethyl-4-phenylsulfanyl-cyclohexa-1,3-dienyl)-but-3-en-2-one

13215-88-8

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaBH4 / methanol / 0.5 h / 0 °C
2: 2 N HCl / 0.5 h / Ambient temperature
View Scheme

N'-[(E)-1-Methyl-3-(2,6,6-trimethyl-cyclohexa-1,3-dienyl)-prop-2-en-(E)-ylidene]-hydrazinecarboxylic acid ethyl ester

13215-88-8

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2.) DBU / 1.) CH2Cl2, -30 deg C, 15 min, 2.) 0 deg C to r.t., 1 h
2: CH2O / tetrahydrofuran; H2O / 1 h / Ambient temperature
3: NaBH4 / methanol / 0.5 h / 0 °C
4: 2 N HCl / 0.5 h / Ambient temperature
View Scheme

N'-[(E)-1-Methyl-3-(2,6,6-trimethyl-4-phenylsulfanyl-cyclohexa-1,3-dienyl)-prop-2-en-(E)-ylidene]-hydrazinecarboxylic acid ethyl ester

13215-88-8

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CH2O / tetrahydrofuran; H2O / 1 h / Ambient temperature
2: NaBH4 / methanol / 0.5 h / 0 °C
3: 2 N HCl / 0.5 h / Ambient temperature
View Scheme
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  • 2-Cyclohexen-1-one,4-(2-buten-1-ylidene)-3,5,5-trimethyl-

  • Casno:

    13215-88-8

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Specification

The Tabanone is an organic compound with the formula C13H18O. The IUPAC name of this chemical is (4Z)-4-[(E)-but-2-enylidene]-3,5,5-trimethylcyclohex-2-en-1-one. With the CAS registry number 13215-88-8, it is also named as 2-Cyclohexen-1-one, 4-(2-buten-1-ylidene)-3,5,5-trimethyl-.

Physical properties about Tabanone are: (1)ACD/LogP: 3.38; (2)ACD/LogD (pH 5.5): 3.38; (3)ACD/LogD (pH 7.4): 3.38; (4)ACD/BCF (pH 5.5): 218.47; (5)ACD/BCF (pH 7.4): 218.47; (6)ACD/KOC (pH 5.5): 1644.92; (7)ACD/KOC (pH 7.4): 1644.92; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 17.07 Å2; (11)Index of Refraction: 1.539; (12)Molar Refractivity: 61.63 cm3; (13)Molar Volume: 196.4 cm3; (14)Polarizability: 24.43×10-24cm3; (15)Surface Tension: 35 dyne/cm; (16)Density: 0.968 g/cm3; (17)Flash Point: 124.8 °C; (18)Enthalpy of Vaporization: 52.85 kJ/mol; (19)Boiling Point: 289.2 °C at 760 mmHg; (20)Vapour Pressure: 0.00223 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1/C=C(\C(=C/C=C/C)C(C)(C)C1)C
(2)InChI: InChI=1/C13H18O/c1-5-6-7-12-10(2)8-11(14)9-13(12,3)4/h5-8H,9H2,1-4H3/b6-5+,12-7+
(3)InChIKey: CBQXHTWJSZXYSK-DVIJZSFDBP
(4)Std. InChI: InChI=1S/C13H18O/c1-5-6-7-12-10(2)8-11(14)9-13(12,3)4/h5-8H,9H2,1-4H3/b6-5+,12-7+
(5)Std. InChIKey: CBQXHTWJSZXYSK-DVIJZSFDSA-N