Cycloheptadec-9-en-1-one supplier

Name
CIVETONE
EINECS 208-813-4
CAS No. 542-46-1
Article Data24
CAS DataBase
Density 0.859 g/cm³
Solubility
Melting Point 31-32°
Formula C₁₇H₃₀O
Boiling Point 371.4 °C at 760 mmHg
Molecular Weight 250.425
Flash Point 157.1 °C
Transport Information
Appearance
Safety 36/37
Risk Codes 38
Molecular Structure
Hazard Symbols Xi
Synonyms 9-Cycloheptadecen-1-one,(9Z)-;(Z)-9-Cycloheptadecen-1-one;Civetone;Civettone, alpha-trans-;FEMA No. 3425;9-Cycloheptadecen-1-one, (9Z)-;(9Z)-cycloheptadec-9-en-1-one;9-Cycloheptadecen-1-one, (Z)-;3-07-00-00524 (Beilstein Handbook Reference);9-Cycloheptadecen-1-one, cis-;9-CYCLOHEPTADECEN-1-ONE, (Z)-(8CI,9CI);
PSA 17.07000
LogP 5.58670

Synthetic route

: 365439-63-0
(Z)-2-methoxycarbonyl-9-cycloheptadecenoate

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Stage #1: (Z)-2-methoxycarbonyl-9-cycloheptadecenoate With sodium hydroxide In methanol for 1h; Heating; Stage #2: With sulfuric acid In methanol for 0.5h; pH=1; Heating; Further stages.;	95%
With sulfuric acid In sodium hydroxide; ethanol	95%

: 32357-36-1
cycloheptadec-9-yn-1-one

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
With quinoline; hydrogen; Lindlar's catalyst In dichloromethane at 20℃; under 760 Torr; for 2h; Lindlar hydrogenation;	94%
With hydrogen; Lindlar's catalyst In hexane for 0.166667h; Ambient temperature;

: 157622-74-7
2-ethoxycarbonyl-9-cycloheptadecenone

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; ethanol at 80℃; for 5h;	93%

: 91874-18-9
(2E,9Z)-Cycloheptadeca-2,9-dienone

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride; copper(ll) bromide	91%

: 135618-36-9
nonadeca-1,18-dien-10-one

A: 542-46-1
(Z)-civetone

B: 1502-37-0
trans-9-Cycloheptadecen-1-one

Conditions

Conditions	Yield
With [2-(1-methylethoxy-κO)phenylmethyl-κC](nitrato-κO,κO′){rel-(2R,5R,7S)-tricyclo[3.3.1.13,7]decane-2,1-diyl[3-(2,4,6-trimethylphenyl)-1-imidazolidinyl-2-ylidene]}ruthenium In 1,2-dichloro-ethane at 60℃; under 0.02 Torr; for 8h; Glovebox; Inert atmosphere; stereoselective reaction;	A 62% B n/a
With Grubbs catalyst first generation In dichloromethane for 2h; Inert atmosphere; Reflux; Overall yield = 33 %; Overall yield = 40 mg; diastereoselective reaction;	A n/a B n/a
With hydrogenchloride; C49H54Cl2N4Ru In ethyl acetate at 110℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox; Overall yield = 52 %;	A n/a B n/a
Stage #1: nonadeca-1,18-dien-10-one With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 14h; Reflux; Glovebox; Inert atmosphere; Stage #2: With ethyl vinyl ether In dichloromethane at 20℃; for 2h; Reagent/catalyst; Solvent; Temperature; Glovebox; Inert atmosphere;

: 135618-36-9
nonadeca-1,18-dien-10-one

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
With C35H47N3O4Ru In dichloromethane at 60℃; for 24h; Sealed tube; Inert atmosphere;	36%

: 1-(aminomethyl)-cyclohexadec-8-enol

A: 542-46-1
(Z)-civetone

B: 4598-76-9
(Z)-cycloheptadec-8-en-1-one

C: 4598-76-9
(E)-cycloheptadec-8-en-1-one

D: 1502-37-0
trans-9-Cycloheptadecen-1-one

Conditions

Conditions	Yield
With acetic acid; sodium nitrite In water at 5 - 10℃; for 2h; Product distribution / selectivity; Tiffeneau-Demjanov-Reaction; Heating / reflux;	A 15% B 15% C 32% D 35%

...Expand

: 3100-36-5
(E/Z)-cyclohexa-dec-8-enone

A: 542-46-1
(Z)-civetone

B: 4598-76-9
(Z)-cycloheptadec-8-en-1-one

C: 4598-76-9
(E)-cycloheptadec-8-en-1-one

D: 1502-37-0
trans-9-Cycloheptadecen-1-one

Conditions

Conditions	Yield
Stage #1: (E/Z)-cyclohexa-dec-8-enone With potassium hydroxide; N-methyl-N-nitrosotoluene-p-sulfonamide In ethanol; water at 3℃; Tiffeneau-Demjanov-Reaction; Stage #2: With hydrogenchloride In ethanol; water pH=2; Product distribution / selectivity;	A 16% B 15% C 33% D 34%

...Expand

: 73125-62-9
(E,E)-2,16-Cycloheptadecadien-9-in-1-on

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
With hydrogen; palladium on barium sulfate In pyridine

: 50768-04-2
9-Cyclononadecinon

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
With hydrogen; Lindlar's catalyst In ethyl acetate

cerium-salt of/the/ octadecene-(9)-dioic acid: cerium-salt of/the/ octadecene-(9)-dioic acid

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
at 300 - 500℃; unter vermindertem Druck;

thorium-salt of/the/ octadecene-(9)-dioic acid: thorium-salt of/the/ octadecene-(9)-dioic acid

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
at 300 - 500℃; unter vermindertem Druck;

1.1-ethylenedioxy-cycloheptadecanediole-(9.10): 1.1-ethylenedioxy-cycloheptadecanediole-(9.10)

A: 542-46-1
(Z)-civetone

B: 1502-37-0
trans-9-Cycloheptadecen-1-one

Conditions

Conditions	Yield
With Acetyl bromide; hydrogen bromide; acetic acid 8-stdg. Kochen des gebildeten 10-Brom-9-acetoxy-cycloheptadecanons-(1) in Aethanol mit Zink und wss. Essigsaeure unter Zusatz von CuSO4 und Behandeln des Reaktionsprodukts mit KOH in Aethanol;

: (Z)-17-Oxo-cycloheptadec-8-enecarboxylic acid

A: 542-46-1
(Z)-civetone

B: 1502-37-0
trans-9-Cycloheptadecen-1-one

Conditions

Conditions	Yield
With sulfuric acid In tetrahydrofuran; methanol for 0.166667h; Decarboxylation; Heating; Title compound not separated from byproducts;

: 504-54-1
(9Z,26Z)-pentatriaconta-9,26-dien-18-one

A: 1779-13-1
octadeca-9Z-ene

B: 542-46-1
(Z)-civetone

C: 1502-37-0
trans-9-Cycloheptadecen-1-one

Conditions

Conditions	Yield
[Ru2(=CHPh)2(C2F5CO2)2(μ-C2F5CO2)2(PCy3)2(μ-H2O)] In hexane; dichloromethane at 20℃;

...Expand

: 1488-78-4
2,19-heneicosadiyn-11-one

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / (t-BuO)3WCCMe3 / toluene / 0.5 h / 80 °C 2: 94 percent / quinoline; H2 / Lindlar-Pd / CH2Cl2 / 2 h / 20 °C / 760 Torr View Scheme

: 9-undecynal

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 58 percent / tetrahydrofuran / 10 h / 20 °C 2: 91 percent / PDC / CH2Cl2 / 16 h / 20 °C 3: 65 percent / (t-BuO)3WCCMe3 / toluene / 0.5 h / 80 °C 4: 94 percent / quinoline; H2 / Lindlar-Pd / CH2Cl2 / 2 h / 20 °C / 760 Torr View Scheme

: 8-decynylmagnesium bromide

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 58 percent / tetrahydrofuran / 10 h / 20 °C 2: 91 percent / PDC / CH2Cl2 / 16 h / 20 °C 3: 65 percent / (t-BuO)3WCCMe3 / toluene / 0.5 h / 80 °C 4: 94 percent / quinoline; H2 / Lindlar-Pd / CH2Cl2 / 2 h / 20 °C / 760 Torr View Scheme

: 307324-15-8
2,19-heneicosadiyn-11-ol

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / PDC / CH2Cl2 / 16 h / 20 °C 2: 65 percent / (t-BuO)3WCCMe3 / toluene / 0.5 h / 80 °C 3: 94 percent / quinoline; H2 / Lindlar-Pd / CH2Cl2 / 2 h / 20 °C / 760 Torr View Scheme

: 2-methoxycarbonyl-9-cycloheptadecenoate

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 percent aqueous NaOH / methanol; tetrahydrofuran / 5 h / 70 °C 2: 10 percent aqueous H2SO4 / methanol; tetrahydrofuran / 0.17 h / Heating View Scheme

: 112-80-1
cis-Octadecenoic acid

(+)-camphor-β-sulfonic acid: (+)-camphor-β-sulfonic acid

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: conc. H2SO4 / 2 h / 110 °C 2: 99 percent / WCl6, SnMe4 / benzene / 20 h / 70 °C 3: 63 percent / KH / tetrahydrofuran; pentane / 1 h / 55 °C 4: 93 percent / aq. NaOH / ethanol; tetrahydrofuran / 5 h / 80 °C View Scheme

: 111-62-6
oleic acid ethyl ester

air: air

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / WCl6, SnMe4 / benzene / 20 h / 70 °C 2: 63 percent / KH / tetrahydrofuran; pentane / 1 h / 55 °C 3: 93 percent / aq. NaOH / ethanol; tetrahydrofuran / 5 h / 80 °C View Scheme

: 80060-80-6
diethyl (Z)-9-octadecene-1,18-dioate

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / KH / tetrahydrofuran; pentane / 1 h / 55 °C 2: 93 percent / aq. NaOH / ethanol; tetrahydrofuran / 5 h / 80 °C View Scheme

: 91873-94-8
6-(1,3-dioxolan-2-yl)-hexanal

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 65 percent 2: 80 percent 3: 1.) HCl; 2.) pH 8.4 4: 91 percent / NaAlH2(O-CH2-CH2-OCH3)2/CuBr2 View Scheme

: 91873-93-7
methyl 6-(1,3-dioxolan-2-yl)hexanoate

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 71 percent / NaAlH2(O-CH2-CH2-OCH3)2 2: 65 percent 3: 80 percent 4: 1.) HCl; 2.) pH 8.4 5: 91 percent / NaAlH2(O-CH2-CH2-OCH3)2/CuBr2 View Scheme

: 91874-16-7
(Z)-15-[1,3]Dioxolan-2-yl-pentadec-9-enoic acid

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent 2: 1.) HCl; 2.) pH 8.4 3: 91 percent / NaAlH2(O-CH2-CH2-OCH3)2/CuBr2 View Scheme

: 91874-17-8
(Z)-16-[1,3]Dioxolan-2-yl-1-(triphenyl-λ5-phosphanylidene)-hexadec-10-en-2-one

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) HCl; 2.) pH 8.4 2: 91 percent / NaAlH2(O-CH2-CH2-OCH3)2/CuBr2 View Scheme

: 91874-15-6
Sodium; 9-(triphenyl-λ5-phosphanylidene)-nonanoate

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 65 percent 2: 80 percent 3: 1.) HCl; 2.) pH 8.4 4: 91 percent / NaAlH2(O-CH2-CH2-OCH3)2/CuBr2 View Scheme

: C19H36N4O2

: 542-46-1
(Z)-civetone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) O2, Py, (ii) aq. HCl 2: H2 / Lindlar catalyst / hexane / 0.17 h / Ambient temperature View Scheme

: 542-46-1
(Z)-civetone

: 4429-77-0
cycloheptadecanol

Conditions

Conditions	Yield
With sodium tetrahydroborate; palladium on activated charcoal; acetic acid In isopropyl alcohol at 20℃; for 14h;	95%

: 542-46-1
(Z)-civetone

: 1774-47-6
trimethylsulfoxonium iodide

: 1370650-35-3
(11Z)-1-oxaspiro[2.16]nonadec-11-ene

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 50℃;	94%

: 67-56-1
methanol

: 542-46-1
(Z)-civetone

: 1370650-42-2
methyl (1Z,9Z)-cyclohexadeca-1,9-diene-1-carboxylate

Conditions

Conditions	Yield
With iodine; potassium hydroxide at -5 - 0℃; Favorskii rearrangement; stereospecific reaction;	7%

: 542-46-1
(Z)-civetone

: 1588-95-0, 67229-08-7, 98804-07-0
(cis-zibetone)-semicarbazone

: 542-46-1
(Z)-civetone

: 3661-77-6
cycloheptadecanone

Conditions

Conditions	Yield
With ethanol; platinum
With acetic acid; platinum
With diethyl ether; platinum Hydrogenation;

: 542-46-1
(Z)-civetone

: 107-21-1
ethylene glycol

: 5949-31-5
1,4-dioxa-spiro[4.16]heneicos-13t-ene

Conditions

Conditions	Yield
With benzenesulfonic acid; benzene Unter Entfernen des entstehenden Wassers;

: 542-46-1
(Z)-civetone

: 100-63-0
phenylhydrazine

: 117900-63-7
[13Z]-5,6,7,8,9,10,11,12,15,16,17,18,19,20-tetradecahydro-cycloheptadec[b]indole

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid

: 542-46-1
(Z)-civetone

A: (12Z)-5,6,7,8,9,10,11,14,15,16,17,18,19,20-tetradecahydro-tetrazoloazacyclooctadecine

B cis-zibetone isooxime: cis-zibetone isooxime

Conditions

Conditions	Yield
With hydrogenchloride; tris-(2-chloro-ethyl)-amine; benzene

: 7647-01-0
hydrogenchloride

: 542-46-1
(Z)-civetone

: 71-43-2
benzene

2 mol HN3: 2 mol HN3

1-amino-heptadecen-(8)-oic acid (17)-lactam: 1-amino-heptadecen-(8)-oic acid (17)-lactam

...Expand

: 7647-01-0
hydrogenchloride

: 542-46-1
(Z)-civetone

: 71-43-2
benzene

8 mol HN3: 8 mol HN3

5.6.7.8.9.10.11.14.15.16.17.18.19.20-tetradecahydro-tetrazoloazacyclooctadecine: 5.6.7.8.9.10.11.14.15.16.17.18.19.20-tetradecahydro-tetrazoloazacyclooctadecine

...Expand

Cycloheptadec-9-en-1-one Consensus Reports

Reported in EPA TSCA Inventory.

Cycloheptadec-9-en-1-one Specification

The cis-Civetone is an organic compound with the formula C₁₇H₃₀O. The IUPAC name of this chemical is (9Z)-cycloheptadec-9-en-1-one. With the CAS registry number 542-46-1, it is also named as (Z)-9-cycloheptadecen-1-one. The product's classification code is Skin / Eye Irritant. Besides, it should be stored in a ventilated and cool place.

Physical properties about cis-Civetone are: (1)ACD/LogP: 6.48; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.48; (4)ACD/LogD (pH 7.4): 6.48; (5)ACD/BCF (pH 5.5): 49384.45; (6)ACD/BCF (pH 7.4): 49384.45; (7)ACD/KOC (pH 5.5): 79662.46; (8)ACD/KOC (pH 7.4): 79662.46; (9)#H bond acceptors: 1; (10)Polar Surface Area: 17.07 Å²; (11)Index of Refraction: 1.448; (12)Molar Refractivity: 78.13 cm³; (13)Molar Volume: 291.3 cm³; (14)Polarizability: 30.97×10^-24cm³; (15)Surface Tension: 28.6 dyne/cm; (16)Density: 0.859 g/cm³; (17)Flash Point: 157.1 °C; (18)Enthalpy of Vaporization: 61.84 kJ/mol; (19)Boiling Point: 371.4 °C at 760 mmHg; (20)Vapour Pressure: 1.04E-05 mmHg at 25°C.

Preparation: the civet liquid caustic soda by 10% KOH-based ethanol, will be the neutral part of the vacuum distillation, collecting 130-170 °C (0.2kPa) fractions, converting them into ammonia urea reduction, separation refining, and then oxalic acid decomposition, may civet ketone. Ketones in the separation of civet civet residue also contains mellow, phthalates can be used to isolate and alkalization, and then use chromic acid oxidation of ketones derived from civet. Synthesis method can be extracted from natural shellac obtained 9,10,16 - trihydroxy-16 acid as raw material, halogenated, elimination of chloride of thionyl chloride, and ethyl acetoacetate condensation, decarboxylation, esterification, iodine cyclization, hydrolysis and other steps to be obtained; It also available from the starting system of oleic acid or 11 to take the goods.

Uses of cis-Civetone: it is used to sulan heart, oriental flavor, citrus Cologne and many floral type, such as large flower jasmine, prynne, narcissus, rose essence and is useful for fixed deodorant. It is indispensable for the preparation of artificial civet spices, the general amount of 1% -2%. It is also used as a substitute for musk. It has a strong ability to be fragrant and often act to deodorant. It can be used for blending high-level essence, in the perfume in the amount of 0.04-0.4% in the balm and lotion in the amount of 0.003-0.02%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1CCCCCCC\C=C/CCCCCCC1
(2)InChI: InChI=1/C17H30O/c18-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-17/h1-2H,3-16H2/b2-1-
(3)InChIKey: ZKVZSBSZTMPBQR-UPHRSURJBS
(4)Std. InChI: InChI=1S/C17H30O/c18-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-17/h1-2H,3-16H2/b2-1-
(5)Std. InChIKey: ZKVZSBSZTMPBQR-UPHRSURJSA-N

Product Name

CIVETONE

Synthetic route

Cycloheptadec-9-en-1-one Consensus Reports

Cycloheptadec-9-en-1-one Specification

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