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502-72-7 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 502-72-7 differently. You can refer to the following data:
1. WHITE CRYSTALLINE POWDER
2. Cyclopentadecanone is a musk fragrance found in the scent gland of the male civet cat. A number of syntheses have been developed for its manufacture [260]. Among these, the so-called Story procedure is the only route that has the potential to make cyclopentadecanone available on a larger scale, but due to the handling of hydroperoxides, the process is difficult to manage. The process starts from tricyclohexylidene triperoxide, which is obtained by oxidation of cyclohexanone with hydrogen peroxide. Pyrolysis leads to a mixture of 1,16-hexadecanolide and cyclopentadecane. The latter is oxidized by oxygen under boric acid catalysis to cyclopentadecanol, which is subsequently oxidized to cyclopentadecanone. Due to the availability of long-chained aliphatic dicarboxylic acids by biotechnological processes, a Dieckmann condensation reaction may also possibly be a useful route to produce this macrocyclic ketone. Cyclopentadecanone is used in fine fragrances:

Occurrence

Reported to be found in the scent glands of the Louisiana muskrat Ondatra zibethicus rivalicius (Guenther, 1949).

Uses

Cyclopentadecanone is the main odoriferous component of musk.

Preparation

By the cyclization of dinitriles in high dilution (Bedoukian. 1967).

Synthesis Reference(s)

Chemistry Letters, 7, p. 1283, 1978The Journal of Organic Chemistry, 36, p. 3266, 1971 DOI: 10.1021/jo00821a003

Toxicity evaluation

Both the acute oral LD50 value in rats and the acute dermal LD50 value in rabbits exceeded 5 g/kg (Moreno. 1975). The acute ip LD100 of cyclopentadecanone was not reached but was estimated to be >35mmol/kg for mice; an ip dose of 11-25 mmol/kg caused no deaths in 24 hr and one of 8-92 mmol/kg caused no deaths in 4 days (the length of the study). An oral dose of ≥45 mmol/kg caused no deaths in mice. Intense agitation accompanied by catatonia of the tail was caused by low doses of cyclopentadecanone; gross examination of the mice revealed no specific pathology but occasionally degenerative hepatitis, proximal tubular nephritis and, rarely, pancreatic necrosis were found following dosing with cycloalkanones (Caujolle & Caujolle, 1965).

Flammability and Explosibility

Nonflammable

Metabolism

Ketones are not readily metabolized, although most of them probably undergo appreciable reduction to the corresponding secondary alcohols, which are excreted in the urine as glucuronic acid conjugates (Williams, 1959). Cyclopentadecanone was hydroxylated in cultures of four steroid-hydroxylating fungi (Calonectria decora, Rhizopus nigricans, Daedalea rufescens and Ophiobolus herpotrichus), but was not affected by Aspergillus ochraceus. Initial attack occurred at the most remote carbon atom, with yields of up to 26% of 8-hydroxycyclopentadecanone, plus dihydroxy compounds and more polar products (Ashton, Bailey & Jones, 1974).

Purification Methods

Subliming Exaltone is better than crystallising it from aqueous EtOH for purification. The semicarbazone has m 186-187o. [Stevens & Erickson J Am Chem Soc 64 146 1942, Mathur et al. J Chem Soc 3505 1963, Biens & Hess Helv Chim Acta 71 1704 1988, Beilstein 7 III 203, 7 IV 118.]

Check Digit Verification of cas no

The CAS Registry Mumber 502-72-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 2 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 502-72:
(5*5)+(4*0)+(3*2)+(2*7)+(1*2)=47
47 % 10 = 7
So 502-72-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H28O/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-15/h1-14H2

502-72-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A17652)  Cyclopentadecanone, 99%   

  • 502-72-7

  • 1g

  • 132.0CNY

  • Detail
  • Alfa Aesar

  • (A17652)  Cyclopentadecanone, 99%   

  • 502-72-7

  • 5g

  • 642.0CNY

  • Detail
  • Alfa Aesar

  • (A17652)  Cyclopentadecanone, 99%   

  • 502-72-7

  • 25g

  • 2724.0CNY

  • Detail

502-72-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclopentadecanone

1.2 Other means of identification

Product number -
Other names Normuscon

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:502-72-7 SDS

502-72-7Synthetic route

cyclopentadecanol
4727-17-7

cyclopentadecanol

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With Amberlyst A26 resin bound bis(azido)iodate(I) In acetonitrile at 20℃; for 18h; Irradiation; Inert atmosphere;100%
With iodine; [bis(pyridine)iodine]+ tetrafluoroborate; caesium carbonate In acetonitrile at 60℃; for 7h;92%
With chromium(VI) oxide; sulfuric acid; benzene
2-Oxocyclopentadecancarbonsaeure-methylester
52794-21-5

2-Oxocyclopentadecancarbonsaeure-methylester

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 3h; Heating;100%
cyclopentadecanone oxime
34341-05-4

cyclopentadecanone oxime

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With 2,2'-dipyridyldiselenide; trimethylphosphane In tetrahydrofuran; toluene at 20℃; for 0.5h; Product distribution; Further Variations:; Reagents; Solvents;100%
With diphenyldisulfane; triethylphosphine In tetrahydrofuran for 0.333333h; Ambient temperature;92%
Stage #1: cyclopentadecanone oxime With diphenyldisulfane; trimethylphosphane In tetrahydrofuran at 20℃;
Stage #2: With water In tetrahydrofuran Further stages.;
With gold(III) tribromide; dimethylglyoxal In ethanol; water at 20℃; for 15h; pH=7;100 %Spectr.
(2E)-cyclopentadec-2-en-1-one
56345-01-8

(2E)-cyclopentadec-2-en-1-one

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal100%
cyclopentadec-4-yn-1-one
14224-80-7

cyclopentadec-4-yn-1-one

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; under 3750.38 Torr; for 8h; Temperature; Autoclave;99%
cyclopentadecanone ethylene acetal
184-41-8

cyclopentadecanone ethylene acetal

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With hydrogenchloride In methanol98%
cyclopentadec-2-en-1-one
32247-08-8

cyclopentadec-2-en-1-one

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With enone reductase from Sporidiobolus salmonicolor TPU 2001; NADH In aq. phosphate buffer at 30℃; for 1h; pH=7; Kinetics; Enzymatic reaction;97.5%
(3E,7E,9E)-Cyclopentadeca-3,7,9-trienone

(3E,7E,9E)-Cyclopentadeca-3,7,9-trienone

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate95%
trans-cyclopentadec-5-enone
57969-18-3

trans-cyclopentadec-5-enone

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol91%
cyclopentadeca-4E,12E-dien-1-one

cyclopentadeca-4E,12E-dien-1-one

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With hydrogen; palladium In ethanol88%
2-(2-Azaheptyliden)cyclopentadecanon

2-(2-Azaheptyliden)cyclopentadecanon

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 15h; Heating;86%
N'-cyclopentadecylidene-4-methylbenzenesulfonohydrazide
56888-60-9

N'-cyclopentadecylidene-4-methylbenzenesulfonohydrazide

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
Envirocat EPZG In water; acetone at 80℃; for 3h;86%
5-Iodo-cyclopentadecanone
114340-69-1

5-Iodo-cyclopentadecanone

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Irradiation;80%
N-Cyclopentadecylidene-N'-methyl-hydrazine
133932-56-6

N-Cyclopentadecylidene-N'-methyl-hydrazine

A

cyclopentadecanone
502-72-7

cyclopentadecanone

B

1,1-Difluorocyclopentadecane

1,1-Difluorocyclopentadecane

Conditions
ConditionsYield
With iodine monofluoride In chloroformA 5%
B 80%
(E)-1-Nitro-cyclopentadecene

(E)-1-Nitro-cyclopentadecene

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With sodium tetrahydroborate; dihydrogen peroxide; potassium carbonate In methanol for 20h; Ambient temperature;80%
dimethyl hexadecanedioate
19102-90-0

dimethyl hexadecanedioate

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
TiO2 + 2 % K2O In tetrahydrofuran at 350℃; Gas phase;78%
With potassium tert-butylate In decalin at 190℃; for 48h;6%
With N-ethyl-N-phenylamine; sodium- anschl. mit wss. H2SO4;
5-Hydroxy-cyclopentadecanon
35720-56-0

5-Hydroxy-cyclopentadecanon

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
78%
2-hydroxycyclopentadecanone
4727-18-8

2-hydroxycyclopentadecanone

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With hydrogenchloride; zinc In 1,4-dioxane; water at 95 - 100℃; for 17h;77%
With hydrogenchloride; ethanol; zinc
With hydrogen; 5%-palladium/activated carbon In toluene at 250℃; under 7500.75 Torr; for 1 - 5h;62 - 93 %Chromat.
Cyclopentadecanone hydrazone
133932-51-1

Cyclopentadecanone hydrazone

A

cyclopentadecanone
502-72-7

cyclopentadecanone

B

1,1-Difluorocyclopentadecane

1,1-Difluorocyclopentadecane

Conditions
ConditionsYield
With iodine monofluoride In chloroform at 25℃;A 50%
B 40%
1,2,10,11-tetraoxocyclotricosane-3,6,9,12,23-pentaone
106051-54-1

1,2,10,11-tetraoxocyclotricosane-3,6,9,12,23-pentaone

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
thermal decomposition;40%
methyl cis-16-oxabicyclo[13.1.0]hexadecane-1-carboxylate

methyl cis-16-oxabicyclo[13.1.0]hexadecane-1-carboxylate

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
Stage #1: methyl cis-16-oxabicyclo[13.1.0]hexadecane-1-carboxylate With methanol; water; sodium hydroxide for 5h; Reflux;
Stage #2: With hydrogenchloride; methanol; water for 1h; Reflux;
33%
diethyl hexadecanedioate
15786-31-9

diethyl hexadecanedioate

A

cyclopentadecanone
502-72-7

cyclopentadecanone

B

cyclotriacontane-1,16-dione
121623-71-0

cyclotriacontane-1,16-dione

Conditions
ConditionsYield
With potassium tert-butylate; xylene
thapsic acid
505-54-4

thapsic acid

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With metal oxide
at 300 - 500℃; Erhitzen von Salzen unter vermindertem Druck;
Thermische Zersetzung des Thoriumsalzes, des Cersalzes oder anderer Salze;
1,16-hexadecanedioyl dichloride
34959-19-8

1,16-hexadecanedioyl dichloride

A

cyclopentadecanone
502-72-7

cyclopentadecanone

B

cyclotriacontane-1,16-dione
121623-71-0

cyclotriacontane-1,16-dione

Conditions
ConditionsYield
With diethyl ether; triethylamine 3-std. Kochen des Reaktionsprodukts mit aethanol. KOH;
With etheric solution; triethylamine Erhitzen des Reaktionsprodukts mit aethanol. KOH;
hexadecanedioic acid-anhydride
1034470-47-7

hexadecanedioic acid-anhydride

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With metal oxide
at 300 - 500℃; Erhitzen von Salzen unter vermindertem Druck;
With metal oxide
at 300 - 500℃; Erhitzen von Salzen unter vermindertem Druck;
diethyl ether
60-29-7

diethyl ether

1,16-hexadecanedioyl dichloride
34959-19-8

1,16-hexadecanedioyl dichloride

triethylamine
121-44-8

triethylamine

A

cyclopentadecanone
502-72-7

cyclopentadecanone

B

cyclotriacontane-1,16-dione
121623-71-0

cyclotriacontane-1,16-dione

Conditions
ConditionsYield
beim Kochen des Reaktionsprodukts mit alkoh. KOH;
tetradeca-1,13-diene
21964-49-8

tetradeca-1,13-diene

Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

A

cyclopentadecanone
502-72-7

cyclopentadecanone

B

2-nonylcyclohexanone
16556-72-2

2-nonylcyclohexanone

Conditions
ConditionsYield
With 9-borabicyclo[3.3.1]nonane dimer; dimethylsulfide borane complex Product distribution;
bicyclo[10.3.0]pentadec-1(12)-en-13-one
15210-25-0

bicyclo[10.3.0]pentadec-1(12)-en-13-one

cyclopentadecanone
502-72-7

cyclopentadecanone

2-Brom-1-cyclopentadecen-1-carbonsaeuremethylester
55676-40-9

2-Brom-1-cyclopentadecen-1-carbonsaeuremethylester

cyclopentadecanone
502-72-7

cyclopentadecanone

Conditions
ConditionsYield
With sodium hydroxide; sodium methylate 1.) methanol, reflux, 5 h, 2.) methanol, water, reflux, 7 h; Yield given. Multistep reaction;
cyclopentadecanone
502-72-7

cyclopentadecanone

1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

1-Naphthylcyclopentadecanol

1-Naphthylcyclopentadecanol

Conditions
ConditionsYield
Stage #1: 1-Bromonaphthalene With iodine; magnesium In diethyl ether Grignard reaction;
Stage #2: cyclopentadecanone In diethyl ether Grignard reaction;
100%
cyclopentadecanone
502-72-7

cyclopentadecanone

1-chloroethyl p-tolyl sulfoxide
50635-71-7, 50635-72-8, 31350-93-3

1-chloroethyl p-tolyl sulfoxide

1-[1-chloro-1-(p-tolylsulfinyl)ethyl]-1-cyclopentadecanol
733016-26-7

1-[1-chloro-1-(p-tolylsulfinyl)ethyl]-1-cyclopentadecanol

Conditions
ConditionsYield
at -70℃;100%
Stage #1: 1-chloroethyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -70℃;
Stage #2: cyclopentadecanone In tetrahydrofuran at -70℃;
Stage #1: 1-chloroethyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: cyclopentadecanone In tetrahydrofuran at -78℃; for 0.25h;
cyclopentadecanone
502-72-7

cyclopentadecanone

5-fluorouridine
316-46-1

5-fluorouridine

5-fluoro-1-[(3a'R,4'R,6'R,6a'R)-3a',4',6',6a'-tetrahydro-6'-(hydroxymethyl)spiro[cyclopentadecane-1,2'-furo[3,4-d][1,3]dioxol]-4'-yl]pyrimidine-2,4(1H,3H)-dione
1251763-86-6

5-fluoro-1-[(3a'R,4'R,6'R,6a'R)-3a',4',6',6a'-tetrahydro-6'-(hydroxymethyl)spiro[cyclopentadecane-1,2'-furo[3,4-d][1,3]dioxol]-4'-yl]pyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 24h;100%
With orthoformic acid triethyl ester In N,N-dimethyl-formamide Acidic conditions;
cyclopentadecanone
502-72-7

cyclopentadecanone

1,1-dichlorocyclopentadecane
102652-64-2

1,1-dichlorocyclopentadecane

Conditions
ConditionsYield
With phosphorus pentachloride In benzene at 0 - 20℃; for 28h;99%
cyclopentadecanone
502-72-7

cyclopentadecanone

(S)-1-amino-2-(methoxymethyl)pyrrolidine
59983-39-0

(S)-1-amino-2-(methoxymethyl)pyrrolidine

Cyclopentadecylidene-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine

Cyclopentadecylidene-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine

Conditions
ConditionsYield
at 70℃; for 20h; Condensation;99%
cyclopentadecanone
502-72-7

cyclopentadecanone

perdeuterated cyclopentadecanone

perdeuterated cyclopentadecanone

Conditions
ConditionsYield
With water-d2; palladium on activated charcoal at 250℃; for 10h;99%
With water-d2; palladium on activated charcoal at 250℃; for 10h;
cyclopentadecanone
502-72-7

cyclopentadecanone

ethylene glycol
107-21-1

ethylene glycol

cyclopentadecanone ethylene acetal
184-41-8

cyclopentadecanone ethylene acetal

Conditions
ConditionsYield
With toluene-4-sulfonic acid In cyclohexane98%
With toluene-4-sulfonic acid In toluene for 16h; Reflux;
cyclopentadecanone
502-72-7

cyclopentadecanone

(1,1-dimethylethyl)diphenylsilyl cyanide
145545-43-3

(1,1-dimethylethyl)diphenylsilyl cyanide

1-<<(1,1-dimethylethyl)diphenylsilyl>oxy>cyclopentadecanecarbonitrile

1-<<(1,1-dimethylethyl)diphenylsilyl>oxy>cyclopentadecanecarbonitrile

Conditions
ConditionsYield
In dichloromethane at 25℃; for 72h;97%
cyclopentadecanone
502-72-7

cyclopentadecanone

chloromethyl p-tolyl sulfoxide
24824-93-9

chloromethyl p-tolyl sulfoxide

1-[Chloro-(toluene-4-sulfinyl)-methyl]-cyclopentadecanol
172467-95-7

1-[Chloro-(toluene-4-sulfinyl)-methyl]-cyclopentadecanol

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78℃;97%
With lithium diisopropyl amide at -78℃;97%
With lithium diisopropyl amide 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 10 min.; Yield given. Multistep reaction;
cyclopentadecanone
502-72-7

cyclopentadecanone

sodium methylate
124-41-4

sodium methylate

methyl cyclotetradec-1-ene-1-carboxylate
892127-39-8

methyl cyclotetradec-1-ene-1-carboxylate

Conditions
ConditionsYield
Stage #1: cyclopentadecanone With bromine In diethyl ether; toluene at 20 - 25℃; for 0.5h;
Stage #2: sodium methylate In toluene at 20 - 25℃; for 0.5h;
97%
cyclopentadecanone
502-72-7

cyclopentadecanone

2,2-dimethoxyethylamine
22483-09-6

2,2-dimethoxyethylamine

N-(2,2-dimethoxyethyl)cyclopentadecanamine

N-(2,2-dimethoxyethyl)cyclopentadecanamine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; Inert atmosphere; Schlenk technique;97%
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere;93%
cyclopentadecanone
502-72-7

cyclopentadecanone

chloromethyl p-tolyl sulfoxide
24824-93-9

chloromethyl p-tolyl sulfoxide

3'-(p-tolylsulfinyl)spiro[cyclopentadecane-1,2'-oxirane]
851662-61-8

3'-(p-tolylsulfinyl)spiro[cyclopentadecane-1,2'-oxirane]

Conditions
ConditionsYield
Stage #1: chloromethyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: cyclopentadecanone In tetrahydrofuran at -78℃;
Stage #3: With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol at 0℃;
94%
cyclopentadecanone
502-72-7

cyclopentadecanone

A

C15H26F2O

C15H26F2O

B

(+/-)-2-fluorocyclopentadecanone

(+/-)-2-fluorocyclopentadecanone

Conditions
ConditionsYield
With sodium dodecyl-sulfate; Selectfluor In water at 80℃; Micellar solution; regioselective reaction;A n/a
B 92%
cyclopentadecanone
502-72-7

cyclopentadecanone

anthranilic acid amide
28144-70-9

anthranilic acid amide

spiro[cyclopentadecane-1,2′(1′H)-quinazolin]-4′(3′H)-one

spiro[cyclopentadecane-1,2′(1′H)-quinazolin]-4′(3′H)-one

Conditions
ConditionsYield
With iodine; zirconium(IV) oxide In neat (no solvent) at 25℃; for 2h; Autoclave; Milling; Green chemistry;91%
cyclopentadecanone
502-72-7

cyclopentadecanone

8-hydroxycyclopentadecanone
55264-50-1

8-hydroxycyclopentadecanone

Conditions
ConditionsYield
With ferredoxin reductase; [2Fe–2S] ferredoxin; cytochrome P450 enzyme CYP101B1 In aq. buffer pH=7.4; Kinetics; Enzymatic reaction;90%
In ethanol (microbiological transformation);
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

cyclopentadecanone
502-72-7

cyclopentadecanone

2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)cyclopentadecan-1-one

2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)cyclopentadecan-1-one

Conditions
ConditionsYield
Stage #1: cyclopentadecanone With lithium chloride; lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.75h; Inert atmosphere;
Stage #2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical With ferrocenium hexafluorophosphate at -78℃; for 0.833333h;
90%
cyclopentadecanone
502-72-7

cyclopentadecanone

(2E)-cyclopentadec-2-en-1-one
56345-01-8

(2E)-cyclopentadec-2-en-1-one

Conditions
ConditionsYield
Stage #1: cyclopentadecanone With chloro-trimethyl-silane; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃;
Stage #2: palladium diacetate In acetonitrile for 2h;
89%
Multi-step reaction with 2 steps
1: tetrahydrofuran / 24 h / 20 °C
2: hydrogen peroxide / tetrahydrofuran; H2O / 1 h
View Scheme
Multi-step reaction with 3 steps
1: diethyl ether / 2 h / Ambient temperature
2: SO2Cl2 / hexane; diethyl ether
3: 92 percent / aq. NaHCO3 / CH2Cl2 / 4 h
View Scheme
cyclopentadecanone
502-72-7

cyclopentadecanone

(phenylthio)methyllithium
13307-75-0

(phenylthio)methyllithium

1-(phenylthiomethyl)cyclopentadecanol
78514-60-0

1-(phenylthiomethyl)cyclopentadecanol

Conditions
ConditionsYield
88%
85%
cyclopentadecanone
502-72-7

cyclopentadecanone

p-methoxy-phenylazide
2101-87-3

p-methoxy-phenylazide

1-(4-methoxyphenyl)-1,4,5,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-1H-cyclopentadeca[d][1,2,3]triazole
1352807-17-0

1-(4-methoxyphenyl)-1,4,5,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-1H-cyclopentadeca[d][1,2,3]triazole

Conditions
ConditionsYield
With L-proline In dichloromethane at 80℃; Sealed tube;87%
cyclopentadecanone
502-72-7

cyclopentadecanone

pentadecanolide
106-02-5

pentadecanolide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 108h;86%
Stage #1: cyclopentadecanone With N-hydroxyphthalimide; 1,1-Diphenylmethanol; 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 75℃; under 760.051 Torr; for 22h; Baeyer-Villiger oxidation;
Stage #2: With 1,1,1,3',3',3'-hexafluoro-propanol; toluene-4-sulfonic acid at 60℃; Baeyer-Villiger oxidation; Inert atmosphere;
70%
With potassium peroxomonosulphate; sulfuric acid; Petroleum ether at 50 - 65℃;

502-72-7Relevant articles and documents

Synthesis of Cyclopentadecanone by Ring Contraction of Cyclohexadecanone

Kato, Tetsuya,Kondo, Hisao,Miyake, Akihisa

, p. 823 - 824 (1980)

Cyclopentadecanone has been synthesized from cyclohexadecanone. 2,2,15-Tribromocyclohexadecanone, upon treatment with sodium methoxide, underwant the Favorskii rearrangement via methyl 2-bromo-1-cyclopentadecene-1-carboxylate to produce a mixture of methyl 2-methoxy-1-cyclopentadecene-1-carboxylate, methyl 2-methoxy-2-cyclopentadecene-1-carboxylate, and methyl 2,2-dimethoxycyclopentadecane-1-carboxylate which was converted into cyclopentadecanone.

Cyclopentadecanone preparation method

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Paragraph 0084; 0085; 0089, (2018/04/28)

The invention provides a cyclopentadecanone preparation method. The method includes that cyclododecene and acryloyl chloride are subjected to reaction to obtain a ketene intermediate shown as a formula (II), the intermediate and a sulfuryl hydrazine compound are subjected to reaction to obtain a hydrazone intermediate shown as a formula (III), and the hydrazone intermediate is subjected to ring opening and hydrogenation to obtain a cyclopentadecanone product shown as a formula (V). Compared with a traditional cyclopentadecanone synthesis route, the method mainly has advantages of low cost andeasiness in acquisition of starting materials, the ketene intermediate shown as the formula (II) is obtained by high-selectivity reaction of cyclododecene and acryloyl chloride, and the integral synthesis route is simple and short in step, high in total yield and applicable to cyclopentadecanone industrial production.

CIRCULAR ECONOMY METHODS OF PREPARING UNSATURATED COMPOUNDS

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Paragraph 0064, (2018/01/18)

Methods of preparing unsaturated compounds or analogs through dehydrogenation of corresponding saturated compounds and/or hydrogenation of aromatic compounds are disclosed.

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