542-46-1

Basic information

• Product Name: CIVETONE
• Synonyms: (z)-9-cycloheptadecen-1-on;(Z)-9-Cycloheptadecen-1-one;10-Ketocycloheptadecene;10-Oxocycloheptadecene;9-Cycloheptadecen-1-one,(Z)-;cis-9-cycloheptadecen-1-one;cis-Civetone;Zibeton
• CAS NO: 542-46-1
• Molecular Formula: C₁₇H₃₀O
• Molecular Weight: 250.42
• EINECS: 208-813-4
• Mol File: 542-46-1.mol
• Article Data: 18

Chemical Properties

• Melting Point: 31-32°
• Boiling Point: bp742 342°; bp2 59°
• Flash Point: 157.1 °C
• Appearance: /
• Density: d433 0.917
• Vapor Pressure: 1.04E-05mmHg at 25°C
• Refractive Index: nD33.4 1.4830
• CAS DataBase Reference: CIVETONE(CAS DataBase Reference)
• NIST Chemistry Reference: CIVETONE(542-46-1)
• EPA Substance Registry System: CIVETONE(542-46-1)

Safety Data

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 36/37
• Hazardous Substances Data: 542-46-1(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 542-46-1 differently. You can refer to the following data:
1. CIVETONE is a colorless liquid with warm, sensual, animalic musky odor and extreme tenacity. It is themain odoriferous constituent of civet.Civetonewas formerly prepared bymultistep syntheses, for example. Recently, newer processes using dimethyl (Z)-9-octadecendioate as starting material have been described. This is cyclized by a Dieckmann condensation either in liquid or in gaseous phase. (Z)-9-Octadecendioic acid is available by microbial oxidation of oleic acid with Candida tropicalis. It is used in fine fragrance compositions for, for example, toiletries and body care products.
2. Cycloheptadeca-9-en-1-one has an obnoxious animal-gland odor. It can be pleasant at extreme dilutions.

Occurrence

In civet (cis-form).

Definition

ChEBI: A macrocycle that is cycloheptadecanone with an unsaturation at position 9 (the 9Z-stereoisomer). It has been found in African Civets.

Preparation

From aleuritic acid, the trans- form only; the cis- and trans-forms from ethyl-9-keto heptadecanedioate.

Safety Profile

A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

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+

Synthetic route

(Z)-2-methoxycarbonyl-9-cycloheptadecenoate (365439-63-0) → (Z)-civetone (542-46-1)

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%

cycloheptadec-9-yn-1-one (32357-36-1) → (Z)-civetone (542-46-1)

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;

2-ethoxycarbonyl-9-cycloheptadecenone (157622-74-7) → (Z)-civetone (542-46-1)

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

(2E,9Z)-Cycloheptadeca-2,9-dienone (91874-18-9) → (Z)-civetone (542-46-1)

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

nonadeca-1,18-dien-10-one (135618-36-9) → (Z)-civetone (542-46-1) + trans-9-Cycloheptadecen-1-one (1502-37-0)

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;

nonadeca-1,18-dien-10-one (135618-36-9) → (Z)-civetone (542-46-1)

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

1-(aminomethyl)-cyclohexadec-8-enol → (Z)-civetone (542-46-1) + (Z)-cycloheptadec-8-en-1-one (4598-76-9) + (E)-cycloheptadec-8-en-1-one (4598-76-9) + trans-9-Cycloheptadecen-1-one (1502-37-0)

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%

(E/Z)-cyclohexa-dec-8-enone (3100-36-5) → (Z)-civetone (542-46-1) + (Z)-cycloheptadec-8-en-1-one (4598-76-9) + (E)-cycloheptadec-8-en-1-one (4598-76-9) + trans-9-Cycloheptadecen-1-one (1502-37-0)

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%

(E,E)-2,16-Cycloheptadecadien-9-in-1-on (73125-62-9) → (Z)-civetone (542-46-1)

Conditions	Yield
With hydrogen; palladium on barium sulfate In pyridine

9-Cyclononadecinon (50768-04-2) → (Z)-civetone (542-46-1)

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

cerium-salt of/the/ octadecene-(9)-dioic acid → (Z)-civetone (542-46-1)

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

thorium-salt of/the/ octadecene-(9)-dioic acid → (Z)-civetone (542-46-1)

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

1.1-ethylenedioxy-cycloheptadecanediole-(9.10) → (Z)-civetone (542-46-1) + trans-9-Cycloheptadecen-1-one (1502-37-0)

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 → (Z)-civetone (542-46-1) + trans-9-Cycloheptadecen-1-one (1502-37-0)

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

(9Z,26Z)-pentatriaconta-9,26-dien-18-one (504-54-1) → octadeca-9Z-ene (1779-13-1) + (Z)-civetone (542-46-1) + trans-9-Cycloheptadecen-1-one (1502-37-0)

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

2,19-heneicosadiyn-11-one (1488-78-4) → (Z)-civetone (542-46-1)

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 → (Z)-civetone (542-46-1)

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 → (Z)-civetone (542-46-1)

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

2,19-heneicosadiyn-11-ol (307324-15-8) → (Z)-civetone (542-46-1)

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 → (Z)-civetone (542-46-1)

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

cis-Octadecenoic acid (112-80-1) + (+)-camphor-β-sulfonic acid → (Z)-civetone (542-46-1)

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

oleic acid ethyl ester (111-62-6) + air → (Z)-civetone (542-46-1)

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

diethyl (Z)-9-octadecene-1,18-dioate (80060-80-6) → (Z)-civetone (542-46-1)

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

6-(1,3-dioxolan-2-yl)-hexanal (91873-94-8) → (Z)-civetone (542-46-1)

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

methyl 6-(1,3-dioxolan-2-yl)hexanoate (91873-93-7) → (Z)-civetone (542-46-1)

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

(Z)-15-[1,3]Dioxolan-2-yl-pentadec-9-enoic acid (91874-16-7) → (Z)-civetone (542-46-1)

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

(Z)-16-[1,3]Dioxolan-2-yl-1-(triphenyl-λ5-phosphanylidene)-hexadec-10-en-2-one (91874-17-8) → (Z)-civetone (542-46-1)

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

Sodium; 9-(triphenyl-λ5-phosphanylidene)-nonanoate (91874-15-6) → (Z)-civetone (542-46-1)

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 → (Z)-civetone (542-46-1)

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

(Z)-civetone (542-46-1) → cycloheptadecanol (4429-77-0)

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

(Z)-civetone (542-46-1) + trimethylsulfoxonium iodide (1774-47-6) → (11Z)-1-oxaspiro[2.16]nonadec-11-ene (1370650-35-3)

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

methanol (67-56-1) + (Z)-civetone (542-46-1) → methyl (1Z,9Z)-cyclohexadeca-1,9-diene-1-carboxylate (1370650-42-2)

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

(Z)-civetone (542-46-1) → (cis-zibetone)-semicarbazone (1588-95-0, 67229-08-7, 98804-07-0)

(Z)-civetone (542-46-1) → cycloheptadecanone (3661-77-6)

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

(Z)-civetone (542-46-1) + ethylene glycol (107-21-1) → 1,4-dioxa-spiro[4.16]heneicos-13t-ene (5949-31-5)

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

(Z)-civetone (542-46-1) + phenylhydrazine (100-63-0) → [13Z]-5,6,7,8,9,10,11,12,15,16,17,18,19,20-tetradecahydro-cycloheptadec[b]indole (117900-63-7)

Conditions	Yield
With hydrogenchloride; acetic acid

(Z)-civetone (542-46-1) → (12Z)-5,6,7,8,9,10,11,14,15,16,17,18,19,20-tetradecahydro-tetrazoloazacyclooctadecine + cis-zibetone isooxime

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

hydrogenchloride (7647-01-0) + (Z)-civetone (542-46-1) + benzene (71-43-2) + 2 mol HN3 → 1-amino-heptadecen-(8)-oic acid (17)-lactam

hydrogenchloride (7647-01-0) + (Z)-civetone (542-46-1) + benzene (71-43-2) + 8 mol HN3 → 5.6.7.8.9.10.11.14.15.16.17.18.19.20-tetradecahydro-tetrazoloazacyclooctadecine

Upstream product

• 32357-36-1 cycloheptadec-9-yn-1-one 
• 365439-63-0 (Z)-2-methoxycarbonyl-9-cycloheptadecenoate 
• 1488-78-4 2,19-heneicosadiyn-11-one 
• 135618-36-9 nonadeca-1,18-dien-10-one 
• 13038-21-6 non-8-en-1-ol 
• 156918-61-5 8-nonene-1-mesylate 
• 74244-64-7 cycloheptadec-9-en-1-one 
• 17344-59-1 (E)/(Z)-cycloheptadec-9-en-1-ol 
• 213207-73-9 10-iodo-1-decene 
• 1351586-51-0 nonadeca-1,18-dien-10-ol 
• 157622-74-7 2-ethoxycarbonyl-9-cycloheptadecenone 
• 91874-18-9 (2E,9Z)-Cycloheptadeca-2,9-dienone 
• 50768-04-2 9-Cyclononadecinon 
• 67233-91-4 trans-9-decenoic acid ethyl ester 

Downstream Products

• 4429-77-0 cycloheptadecanol 
• 101034-26-8 cycloheptadecanone-(2,4-dinitro-phenylhydrazone) 
• 3661-77-6 cycloheptadecanone 

Relevant articles and documents

Ring closing alkyne metathesis: Stereoselective synthesis of civetone

A concise and stereoselective synthesis of the macrocyclic musk civetone 6 is reported starting from readily available 9-undecynol. The key steps comprise a ring closing metathesis of diyne 4 followed by Lindlar reduction of the resulting cycloalkyne 5. The cyclization can be effected either by using catalytic amounts of the Schrock alkylidyne complex (t-BuO)3W=CCMe3 or by means of an in situ catalyst mixture generated from Mo(CO)6 and p-trifluoromethylphenol. Both catalyst systems turned out to be compatible with the unprotected ketone function of the substrate.

Highly selective macrocyclic ring-closing metathesis of terminal olefins in non-chlorinated solvents at low dilution

A set of new ruthenium-indenylidene complexes bearing two unsymmetrical unsaturated N-cycloalkyl-NHC ligands were synthesized. These catalysts proved to be highly selective in the macrocyclic ring-closing metathesis performed in non-chlorinated solvents at low dilution (0.01 M). Without the requirement of benzoquinone derivatives to prevent the isomerisation side reactions, this environmentally friendly catalytic process promoted the synthesis of macrocyclic odorant molecules with remarkable >99% purity.

METHOD OF CYCLIC COMPOUNDS PRODUCTION IN OLEFINE METATHESIS REACTION AND USE OF RUTHENIUM CATALYSTS IN PRODUCTION OF CYCLIC OLEFINS IN OLEFINE METATHESIS REACTION

The invention relates to a method for the preparation of cyclic compounds in the metathesis of olefins from acyclic dienes comprising terminal and/or non-terminal C=C double bonds; the invention also relates to the use of homogeneous ruthenium complexes and homogeneous ruthenium complexes deposited on a solid support as catalysts and/or pre-catalysts for the preparation of cyclic olefins in olefin metathesis reactions. Formula (I)