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28940-11-6

Basic Information
CAS No.: 28940-11-6
Name: Watermelon Ketone
Molecular Structure:
Molecular Structure of 28940-11-6 (Watermelon Ketone)
Formula: C10H10O3
Molecular Weight: 178.18
Synonyms: 7-Methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one;2H-1,5-benzodioxepin-3(4H)-one, 7-methyl-;7-Methyl-2H-1,5-benzodioxepin-3(4H)-one;
EINECS: 249-320-4
Density: 1.196 g/cm3
Melting Point: 37.0 to 41.0 °C
Boiling Point: 305.2 °C at 760 mmHg
Flash Point: 129.3 °C
Solubility:
Appearance: white crystalline powder
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 35.53000
LogP: 1.33530
Synthetic route
1323441-46-8

7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxolane]

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With sulfuric acid In acetone for 6h; Reagent/catalyst; Solvent; Reflux;95%

7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-one oxime

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With sodium nitrite In water; acetonitrile at 40℃; for 10h;94%
944558-65-0

(±)-7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-ol

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With potassium hydroxide; potassium permanganate for 2.5h;87%
Reaxys ID: 11944038

Reaxys ID: 11944038

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With sodium carbonate; potassium iodide In acetone for 4h; Heating / reflux;84.45%
534-07-6

1,3-Dichloroacetone

452-86-8

4-methyl-1,2-dihydroxybenzene

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With sodium carbonate; potassium iodide In butanone for 4.16667h; Heating / reflux;76.24%
With sodium carbonate; potassium iodide In cyclohexanone for 4.41667h; Heating / reflux;75.25%
With sodium carbonate; potassium iodide In acetone for 12h; Heating / reflux;59.91%
816-39-7

1,3-dibromoroacetone

452-86-8

4-methyl-1,2-dihydroxybenzene

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
With sodium carbonate; potassium iodide In acetone for 12h; Heating / reflux;69.95%
52589-39-6

2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
Stage #1: 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.5h; Dieckmann cyclisation;
Stage #2: With hydrogenchloride In ethanol; water for 0.0666667h; microwave irradiation;
Stage #1: 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.5h;
Stage #2: With hydrogenchloride In ethanol at 90℃; for 2h; Further stages.;
0.59 g
Stage #1: 2,2'-[(4-methyl-1,2-phenylene)bis(oxy)]bis[acetic acid] dimethyl ester With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.5h; Dieckmann Condensation; Inert atmosphere;
Stage #2: With hydrogenchloride In ethanol; water at 120℃; for 8h;
944558-64-9

3,4-dihydro-7-methyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-1,5-benzodioxepine

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / vanadium pentoxide; aq. H2O2 / acetonitrile / 70 °C
2: 87 percent / aq. KOH; KMnO4 / 2.5 h
View Scheme
452-86-8

4-methyl-1,2-dihydroxybenzene

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 83 percent / K2CO3 / dimethylformamide / 0.07 h / microwave irradiation
2.1: tBuOK / tetrahydrofuran / 0.5 h / 70 °C
2.2: 0.59 g / aq. HCl / ethanol / 2 h / 90 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide; ammonium iodide / acetone; ethanol / 4 h / Reflux
2: sulfuric acid / acetone / 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide; potassium iodide / ethanol; water / 4 h / Reflux
2: sulfuric acid / acetone / 6 h / Reflux
View Scheme
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-one oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In water; acetonitrile at 50℃; for 24h;94%
With hydroxylamine hydrochloride; sodium acetate In water; acetonitrile at 50℃; for 24h;90%
With hydroxylamine hydrochloride
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

944558-65-0

(±)-7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 25℃; for 1h; Inert atmosphere;92%
With hydrogen In methanol at 100℃; under 30003 Torr; for 12h; Autoclave;91.2%
With sodium tetrahydroborate In methanol; water at 20℃; for 4h;89%
With sodium tetrahydroborate In ethanol for 1h; Reflux;80%
2392-68-9

3-chlorophenyl-isothiocyanate

107-91-5

cyanoacetic acid amide

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1258873-71-0

C20H16ClN3O3S

Conditions
ConditionsYield
Stage #1: 3-chlorophenyl-isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
90%
103-72-0

phenyl isothiocyanate

107-91-5

cyanoacetic acid amide

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1258873-69-6

C20H17N3O3S

Conditions
ConditionsYield
Stage #1: phenyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
89%
1544-68-9

4-fluorophenyl isothiocyanate

107-91-5

cyanoacetic acid amide

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1258873-70-9

C20H16FN3O3S

Conditions
ConditionsYield
Stage #1: 4-fluorophenyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
89%
2131-55-7

4-Chlorophenyl isothiocyanate

107-91-5

cyanoacetic acid amide

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1258873-72-1

C20H16ClN3O3S

Conditions
ConditionsYield
Stage #1: 4-Chlorophenyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
87%
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

7-bromo-8-methyl-2H-1,5-benzodioxepin-3(4H)-one

Conditions
ConditionsYield
With sodium bromate; sodium disulfite In cyclohexane; water at 50℃; for 8h;85%
7357-70-2

Cyanothioacetamide

103-72-0

phenyl isothiocyanate

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1258873-82-3

C20H17N3O2S2

Conditions
ConditionsYield
Stage #1: Cyanothioacetamide; phenyl isothiocyanate With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
82%
622-78-6

Benzyl isothiocyanate

107-91-5

cyanoacetic acid amide

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1258873-68-5

C21H19N3O3S

Conditions
ConditionsYield
Stage #1: Benzyl isothiocyanate; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
81%
1122-82-3

isothiocyanatocyclohexane

107-91-5

cyanoacetic acid amide

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1258873-67-4

C20H23N3O3S

Conditions
ConditionsYield
Stage #1: isothiocyanatocyclohexane; cyanoacetic acid amide With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one With acetic acid In N,N-dimethyl-formamide at 80℃; for 0.133333h; Microwave irradiation;
80%
149-73-5

trimethyl orthoformate

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

3,4-dihydro-3,3-dimethoxy-7-methyl-2H-1,5-benzodioxepine

Conditions
ConditionsYield
With methanol; trifluorormethanesulfonic acid In nitromethane at 100℃; for 3h;72%
109-77-3

malononitrile

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1323441-44-6

2-(7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-ylidene)malononitrile

Conditions
ConditionsYield
With piperidine; acetic acid In benzene Reflux;52%
107-21-1

ethylene glycol

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1323441-46-8

7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxolane]

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 12h; Reflux;45%
504-63-2

trimethyleneglycol

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1323441-47-9

7-methyl-2,4-dihydrospiro[benzo[b][1,4]dioxepine-3,2'-[1,3]dioxane]

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 12h; Reflux;38%
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

3,4-dihydro-7-methyl-2H-1,5-benzodioxepin-3-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / NaBH4 / H2O; methanol / 4 h / 20 °C
2: 88 percent / Et3N / diethyl ether / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / diethyl ether / 1 h / 25 °C / Inert atmosphere
2: pyridine / 2 h / 100 °C / Inert atmosphere
View Scheme
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

3,4-dihydro-7-methyl-2H-1,5-benzodioxepin-3-yl benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / NaBH4 / H2O; methanol / 4 h / 20 °C
2: 44 percent / Et3N / diethyl ether / 2 h / 20 °C
View Scheme
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

3,4-dihydro-7-methyl-2H-1,5-benzodioxepin-3-yl prop-2-enoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / NaBH4 / H2O; methanol / 4 h / 20 °C
2: 22 percent / Et3N / diethyl ether / 2 h / 20 °C
View Scheme
28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

7-methyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / hydroxylamine hydrochloride; AcONa / acetonitrile; H2O / 24 h / 50 °C
2: 54 percent / NaBH4; TiCl4 / 1,2-dimethoxy-ethane / 24 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; sodium acetate / water; acetonitrile / 24 h / 50 °C
2: sodium tetrahydroborate; titanium tetrachloride / diethyl ether / 24 h / 20 °C / Inert atmosphere
View Scheme
105-56-6

ethyl 2-cyanoacetate

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

A

1323441-45-7

cis-ethyl-2-cyano-2-(7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-ylidene)acetate

B

trans-ethyl-2-cyano-2-(7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-ylidene)acetate

Conditions
ConditionsYield
With piperidine; acetic acid In benzene Reflux;
90134-10-4

4-(N,N-dibutylamino)benzaldehyde

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1430403-92-1

7-methyl-2,4-bis[1-(4-dibutylaminophenyl)meth-(Z)-ylidene]benzo[b]-1,4-dioxepin-3-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 50℃; for 40h;1.45 g
4460-86-0

asaraldehyde

28940-11-6

7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one

1430403-79-4

7-methyl-2,4-bis[1-(2,4,5-trimethoxyphenyl)meth-(Z)-ylidene]benzo[b]-1,4-dioxepin-3-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 40℃; for 2h;1.45 g
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Chemistry

1.Introduction of Watermelon Ketone

Watermelon Ketone,with the CAS NO 28940-11-6, is a kind of white powder or crystal.It have Synonyms of 7-Methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-one;2H-1,5-benzodioxepin-3(4H)-one, 7-methyl- and 7-Methyl-2H-1,5-benzodioxepin-3(4H)-one. Watermelon Ketone can be used as flavor ,fragrance and perfume.

2.Properties of Watermelon Ketone

(1) ACD/LogP: 2.747 (2)ACD/LogD (pH 5.5): 2.75 (3) ACD/LogD (pH 7.4): 2.75
(4)ACD/BCF (pH 5.5): 72.11 (5)ACD/BCF (pH 7.4): 72.11 (6)ACD/KOC (pH 5.5): 744.00 (7)ACD/KOC (pH 7.4): 744.00 (8)#H bond acceptors: 3 (9) Polar Surface Area: 35.53 ?2
(10)Index of Refraction: 1.538 (11)Molar Refractivity: 46.593 cm3
(12) Molar Volume: 148.86 cm3 (13)Polarizability: 18.471 10-24cm3
(14)Surface Tension: 40.9850006103516 dyne/cm (15)Density: 1.197 g/cm3
(16) Flash Point: 129.323 °C (17) Enthalpy of Vaporization: 54.568 kJ/mol
(18) Boiling Point: 305.248 °C at 760 mmHg (19)Vapour Pressure: 0.00100000004749745 mmHg at 25°C


3.Structure descriptor of Watermelon Ketone


SMILES:
O=C1COc2c(OC1)cc(cc2)CCopied
Std. InChI:
InChI=1S/C10H10O3/c1-7-2-3-9-10(4-7)13-6-8(11)5-12-9/h2-4H,5-6H2,1H3Copied
Std. InChIKey:
SWUIQEBPZIHZQS-UHFFFAOYSA-N