3661-77-6

Basic information

• Product Name: CYCLOHEPTADECANONE
• Synonyms: CYCLOHEPTADECANONE;Dihydrocivetone;Ai3-38744
• CAS NO: 3661-77-6
• Molecular Formula: C₁₇H₃₂O
• Molecular Weight: 252.44
• Mol File: 3661-77-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 369.66°C (rough estimate)
• Flash Point: 157.9 °C
• Appearance: /
• Density: 0.9652 (rough estimate)
• Vapor Pressure: 4.4E-05mmHg at 25°C
• Refractive Index: 1.4700 (estimate)
• CAS DataBase Reference: CYCLOHEPTADECANONE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOHEPTADECANONE(3661-77-6)
• EPA Substance Registry System: CYCLOHEPTADECANONE(3661-77-6)

Safety Data

• Hazardous Substances Data: 3661-77-6(Hazardous Substances Data)

Usage

Description

Cycloheptadecanone is a cyclic ketone with a 17-carbon backbone, known for its sweet, floral scent and versatile applications across various industries.

Uses

Used in Fragrance and Flavoring Industry:
Cycloheptadecanone is used as a fragrance ingredient for its sweet, floral scent, adding pleasant aromas to various products.
Used in Cosmetic Products:
In the cosmetic industry, cycloheptadecanone is used as a fragrance ingredient, enhancing the sensory experience of the products.
Used in Pharmaceutical Research:
Cycloheptadecanone is studied for its potential pharmaceutical properties, such as anti-inflammatory and analgesic effects, indicating its potential use in developing new medications for pain relief and inflammation management.

InChI:InChI=1/C17H32O/c18-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-17/h1-16H2

Synthetic route

2-hydroxy-cycloheptadecanone (98221-89-7) → cycloheptadecanone (3661-77-6)

Conditions	Yield
With hydrogenchloride; zinc In 1,4-dioxane; water at 95 - 100℃; for 17h;	80%
With hydrogenchloride; zinc In 1,4-dioxane
Multi-step reaction with 2 steps 1: N2H4, NaOH / bis-(2-hydroxy-ethyl) ether / 210 °C 2: CrO3, aq. H2SO4 View Scheme

cycloheptadec-9-en-1-one (74244-64-7) → cycloheptadecanone (3661-77-6)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃;	60%
With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 16h; Schlenk technique; Glovebox;	52%
With ethanol; colloid; palladium Hydrogenation;
Multi-step reaction with 2 steps 1: platinum black; glacial acetic acid / Hydrogenation 2: benzene; Cr2O3-H2SO4 View Scheme
Multi-step reaction with 3 steps 1: sodium; alcohol 2: platinum black; glacial acetic acid / Hydrogenation 3: benzene; Cr2O3-H2SO4 View Scheme

1,16-dicyanododecane (7735-45-7) → cycloheptadecanone (3661-77-6) + cyclotetratriacontane-1,18-dione

Conditions	Yield
With etheric solution; lithium N-ethyl-N-phenylamide Erhitzen des Reaktionsprodukts mit 70prozentig. wss. Schwefelsaeure;

octadecanedioic acid (871-70-5) → cycloheptadecanone (3661-77-6)

Conditions	Yield
With thionyl chloride; benzene anschl. mit Triaethylamin in Benzol bei 40grad;

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

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

cycloheptadecanol (4429-77-0) → cycloheptadecanone (3661-77-6)

Conditions	Yield
With chromium(III) oxide; sulfuric acid; benzene
With chromium(VI) oxide; sulfuric acid

trans-9-Cycloheptadecen-1-one (1502-37-0) → cycloheptadecanone (3661-77-6)

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

diethyl ether (60-29-7) + 1,16-dicyanododecane (7735-45-7) + lithium ethylanilide → cycloheptadecanone (3661-77-6) + cyclotetratriacontane-1,18-dione

Conditions	Yield
und Kochen des Reaktionsprodukts mit 70prozentiger H2SO4;

(+-)-2-imino-cycloheptadecane-carbonitrile-(1) → cycloheptadecanone (3661-77-6)

Conditions	Yield
With sulfuric acid

thorium salt of/the/ hexadecane-dicarboxylic acid-(1.16) → cycloheptadecanone (3661-77-6)

Conditions	Yield
at 350 - 400℃; under 30 - 40 Torr; Thermolysis;
With iron at 350 - 400℃; under 30 - 40 Torr; Thermolysis;
With copper at 350 - 400℃; under 30 - 40 Torr; Thermolysis;

ethanol (64-17-5) + cycloheptadec-9-en-1-one (74244-64-7) + colloidal palladium → cycloheptadecanone (3661-77-6)

Conditions	Yield
Hydrogenation;

cycloheptadecanol (4429-77-0) + benzene (71-43-2) + Cr2O3-H2SO4 → cycloheptadecanone (3661-77-6)

thorium-salt of/the/ octadecanedioic acid → cycloheptadecanone (3661-77-6) + cyclotetratriacontane-1,18-dione

Conditions	Yield
at 300 - 400℃;
at 300 - 400℃;

1-vinyl-cyclopentadecanol (434283-10-0) → cycloheptadecanone (3661-77-6)

Conditions	Yield
at 650℃; under 0.75006 - 3.00024 Torr;

monoethyl sebacate (693-55-0) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 67 percent / sodium methoxide / methanol / 28 °C / Electrolysis 2: sodium / xylene / 2.5 h / Heating 3: 80 percent / zink; hydrogen chloride / dioxane; H2O / 17 h / 95 - 100 °C View Scheme

diethyl heptadecanedioate (42234-86-6) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium / xylene / 2.5 h / Heating 2: 80 percent / zink; hydrogen chloride / dioxane; H2O / 17 h / 95 - 100 °C View Scheme
Multi-step reaction with 2 steps 1: Na / xylene 2: Zn, HCl / dioxane View Scheme

cycloundecanone (878-13-7) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: CeCl3 / tetrahydrofuran / 0.5 h / 20 °C 1.2: tetrahydrofuran / 0.5 h / 25 °C 2.1: 65 percent / 650 °C / 0.75 - 3 Torr 3.1: CeCl3 / tetrahydrofuran / 0.5 h / 20 °C 3.2: tetrahydrofuran / 0.5 h / 25 °C 4.1: 650 °C / 0.75 - 3 Torr 5.1: CeCl3 / tetrahydrofuran / 0.5 h / 20 °C 5.2: tetrahydrofuran / 0.5 h / 25 °C 6.1: 650 °C / 0.75 - 3 Torr View Scheme

cyclopentadecanone (502-72-7) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: CeCl3 / tetrahydrofuran / 0.5 h / 20 °C 1.2: tetrahydrofuran / 0.5 h / 25 °C 2.1: 650 °C / 0.75 - 3 Torr View Scheme

(2E)-cyclopentadec-2-en-1-one (56345-01-8) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 100 percent / H2 / Pd/C 2.1: CeCl3 / tetrahydrofuran / 0.5 h / 20 °C 2.2: tetrahydrofuran / 0.5 h / 25 °C 3.1: 650 °C / 0.75 - 3 Torr View Scheme

cyclotridecanone (832-10-0) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: CeCl3 / tetrahydrofuran / 0.5 h / 20 °C 1.2: tetrahydrofuran / 0.5 h / 25 °C 2.1: 650 °C / 0.75 - 3 Torr 3.1: CeCl3 / tetrahydrofuran / 0.5 h / 20 °C 3.2: tetrahydrofuran / 0.5 h / 25 °C 4.1: 650 °C / 0.75 - 3 Torr View Scheme

1-Vinyl-cycloundecanol (434283-08-6) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 65 percent / 650 °C / 0.75 - 3 Torr 2.1: CeCl3 / tetrahydrofuran / 0.5 h / 20 °C 2.2: tetrahydrofuran / 0.5 h / 25 °C 3.1: 650 °C / 0.75 - 3 Torr 4.1: CeCl3 / tetrahydrofuran / 0.5 h / 20 °C 4.2: tetrahydrofuran / 0.5 h / 25 °C 5.1: 650 °C / 0.75 - 3 Torr View Scheme

1-vinyl-cyclotridecanol (434283-09-7) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 650 °C / 0.75 - 3 Torr 2.1: CeCl3 / tetrahydrofuran / 0.5 h / 20 °C 2.2: tetrahydrofuran / 0.5 h / 25 °C 3.1: 650 °C / 0.75 - 3 Torr View Scheme

(E)-2-methoxycarbonyl-9-cycloheptadecenoate (308240-20-2) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH; aqueous methanol 2: ethanol; platinum View Scheme

E-cycloheptadec-9-enol (17344-59-1) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: platinum black; glacial acetic acid / Hydrogenation 2: benzene; Cr2O3-H2SO4 View Scheme
Multi-step reaction with 3 steps 1: diluted Cr2O3-H2SO4 2: platinum black; glacial acetic acid / Hydrogenation 3: benzene; Cr2O3-H2SO4 View Scheme

9,10,16-trihydroxyhexadecanoic acid (6949-98-0) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: (i) HBr, AcOH, (ii) /BRN= 1718733/, H2SO4, (iii) Zn, EtOH, HBr 2: (i), (ii) aq. KOH 3: (esterification) 4: (hydrogenation) 5: Na / xylene 6: Zn, HCl / dioxane View Scheme

heptadec-8-enedioic acid (93813-37-7) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: (esterification) 2: (hydrogenation) 3: Na / xylene 4: Zn, HCl / dioxane View Scheme

trans-16-Brom-hexadecen-(9)-saeure-ethylester (875763-91-0) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: (i), (ii) aq. KOH 2: (esterification) 3: (hydrogenation) 4: Na / xylene 5: Zn, HCl / dioxane View Scheme

trans-1,15-Bisethoxycarbonyl-pentadecen-(7) (95135-72-1) → cycloheptadecanone (3661-77-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: (hydrogenation) 2: Na / xylene 3: Zn, HCl / dioxane View Scheme

cycloheptadecanone (3661-77-6) + trimethylsulfoxonium iodide (1774-47-6) → 1-oxaspiro[2.16]nonadecane (1370650-43-3)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 50℃;	91%

methanol (67-56-1) + cycloheptadecanone (3661-77-6) → methyl (1Z)-cyclohexadec-1-ene-1-carboxylate (1333501-89-5)

Conditions	Yield
With iodine; potassium hydroxide at -5 - 0℃; Favorskii rearrangement; stereospecific reaction;	50%

methyl magnesium iodide (917-64-6) + cycloheptadecanone (3661-77-6) → 1-methyl-cycloheptadecanol

Conditions	Yield
With diethyl ether

hydrogen cyanide (74-90-8) + cycloheptadecanone (3661-77-6) → 1-hydroxy-cycloheptadecanecarboxylic acid amide

Conditions	Yield
With piperidine anschliessend Behandeln mit 90prozentig. wss. Schwefelsaeure;

cycloheptadecanone (3661-77-6) + sodium cyanide (143-33-9) → 1,3-diaza-spiro[4.16]heneicosane-2,4-dione (5699-86-5)

Conditions	Yield
With ammonium carbonate

cycloheptadecanone (3661-77-6) + nitromalondialdehyde sodium salt (34461-00-2) → 17-nitro-[14]metacyclophan-20-ol

Conditions	Yield
With sodium hydroxide

cycloheptadecanone (3661-77-6) → oxacyclooctadecan-2-one (5637-97-8)

Conditions	Yield
With potassium peroxomonosulphate; sulfuric acid; Petroleum ether at 30 - 50℃;

cycloheptadecanone (3661-77-6) → dihydrocivetone (68263-62-7)

Conditions	Yield
With hydrogen azide; sulfuric acid; benzene unter Kuehlung;

cycloheptadecanone (3661-77-6) → heptadecanedioic acid (2424-90-0)

Conditions	Yield
With chromium(VI) oxide; acetic acid

cycloheptadecanone (3661-77-6) → cycloheptadecanol (4429-77-0)

Conditions	Yield
With ethanol; nickel at 120℃; under 58840.6 Torr; Hydrogenation;
With lithium aluminium tetrahydride; diethyl ether

cycloheptadecanone (3661-77-6) → 2-methyl-cycloheptadecanone (79366-78-2)

Conditions	Yield
With diethyl ether; sodium amide; benzene nachfolgend Kochen mit Methyljodid;

cycloheptadecanone (3661-77-6) + indole-2,3-dione (91-56-5) → 7,8,9,10,11,12,13,14,15,16,17,18,19,20-tetradecahydro-6H-cycloheptadeca[b]quinoline-21-carboxylic acid

Conditions	Yield
With potassium hydroxide

cycloheptadecanone (3661-77-6) + benzaldehyde (100-52-7) → 2-benzylidene-cycloheptadecanone

Conditions	Yield
With sodium hydroxide

cycloheptadecanone (3661-77-6) + benzaldehyde (100-52-7) → 2-(α-hydroxy-benzyl)-cycloheptadecan-1-one

Conditions	Yield
With sodium hydroxide

cycloheptadecanone (3661-77-6) + chloroacetic acid ethyl ester (105-39-5) → 1-oxa-spiro[2.16]nonadecane-2-carboxylic acid amide

Conditions	Yield
With diethyl ether; sodium amide

cycloheptadecanone (3661-77-6) + chloroacetic acid ethyl ester (105-39-5) → cycloheptadecanecarbaldehyde (854450-60-5)

Conditions	Yield
With diethyl ether; sodium amide Behandeln der bei 143-150grad/0,03 Torr siedenden Fraktion des Reaktionsprodukts mit aethanol. KOH und Erhitzen der gebildeten Saeure unter vermindertem Druck;

cycloheptadecanone (3661-77-6) + (2,4-dinitro-phenyl)-hydrazine (119-26-6) → cycloheptadecanone-(2,4-dinitro-phenylhydrazone) (101034-26-8)

cycloheptadecanone (3661-77-6) + Dimethyl phosphite (868-85-9) → 1-Hydroxy-cycloheptadecanyl-(1)-phosphonsaeure-dimethylester (17211-14-2)

Conditions	Yield
With sodium methylate In methanol Ambient temperature;

acetal-aminal of β-dimethylaminoacrolein (5043-86-7) + cycloheptadecanone (3661-77-6) → 2-((E)-1,3-Bis-dimethylamino-allyl)-cycloheptadecanone (75143-13-4)

Conditions	Yield
at 90 - 95℃; for 3h;	0.4 g

Upstream product

• 7735-45-7 1,16-dicyanododecane 
• 871-70-5 octadecanedioic acid 
• 542-46-1 (Z)-civetone 
• 4429-77-0 cycloheptadecanol 
• 74244-64-7 cycloheptadec-9-en-1-one 
• 1502-37-0 trans-9-Cycloheptadecen-1-one 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 71-43-2 benzene 
• 878-13-7 cycloundecanone 
• 502-72-7 cyclopentadecanone 
• 434283-08-6 1-Vinyl-cycloundecanol 
• 95135-72-1 trans-1,15-Bisethoxycarbonyl-pentadecen-⁽⁷⁾ 
• 875763-91-0 trans-16-Brom-hexadecen-⁽⁹⁾-saeure-ethylester 

Downstream Products

• 2424-90-0 heptadecanedioic acid 
• 4429-77-0 cycloheptadecanol 
• 830-13-7 cyclododecanone 
• 63134-81-6 methyl (1Z)-cycloundec-1-ene-1-carboxylate 
• 3603-99-4 cyclotetradecanone 
• 832-10-0 cyclotridecanone 
• 502-72-7 cyclopentadecanone 
• 878-13-7 cycloundecanone 
• 1502-06-3 cyclodecanone 
• 296-19-5 azacyclooctadecane 

Relevant articles and documents

Fluorinated Musk Fragrances: The CF2Group as a Conformational Bias Influencing the Odour of Civetone and (R)-Muscone

The difluoromethylene (CF2) group has a strong tendency to adopt corner over edge locations in aliphatic macrocycles. In this study, the CF2group has been introduced into musk relevant macrocyclic ketones. Nine civetone and five muscone analogues have been prepared by synthesis for structure and odour comparisons. X-ray studies indeed show that the CF2groups influence ring structure and they give some insight into the preferred ring conformations, triggering a musk odour as determined in a professional perfumery environment. The historical conformational model of Bersuker and co-workers for musk fragrance generally holds, and structures that become distorted from this consensus, by the particular placement of the CF2groups, lose their musk fragrance and become less pleasant.

A facile electrochemical approach for the synthesis of macrocyclic alkanones

The synthesis of macrocyclic alkanones, viz. cyclotetradecanone 4a, cyclohexadecanone 4b, cyclooctadecanone 4c, cyclopentadecanone 4d and cycloheptadecanone 4e have been carried out by using Kolbe symmetrical/unsymmetrical dimerization followed by cyclization in Na-xylene and subsequent reduction with Zn-HCI in 70-80% yield. The products of anodic cross coupling have been separated by column chromatography over silica gel (60-120 mesh) by eluting with benzene-methanol (95: 5). An effort has been made to optimize the electrochemical step by investigating the effect of different parameters, viz. degree of partial neutralization, current density and electrode material. The products have been characterised by elemental analyses and IR and 1H NMR spectral data.