137-03-1

Basic information

• Product Name: 2-N-HEPTYLCYCLOPENTANONE
• Synonyms: NSC 78468;2-N-HEPTYLCYCLOPENTANONE;2-HEPTYLCYCLOPENTANONE;2-HEPTYLCYCLOPENTAN-1-ONE;HEPTONE;FLEURAMONE;2-heptyl-cyclopentanon;Alismone
• CAS NO: 137-03-1
• Molecular Formula: C₁₂H₂₂O
• Molecular Weight: 182.3
• EINECS: 205-273-1
• Mol File: 137-03-1.mol

Chemical Properties

• Boiling Point: 264 °C
• Flash Point: 98.565 °C
• Appearance: /
• Density: 0.89
• Vapor Pressure: 0.0204mmHg at 25°C
• Refractive Index: 1.4526 (589.3 nm 20℃)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: 31mg/L at 24℃
• CAS DataBase Reference: 2-N-HEPTYLCYCLOPENTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-HEPTYLCYCLOPENTANONE(137-03-1)
• EPA Substance Registry System: 2-N-HEPTYLCYCLOPENTANONE(137-03-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37
• RTECS: GY4950000
• TSCA: Yes
• Hazardous Substances Data: 137-03-1(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
2-N-HEPTYLCYCLOPENTANONE is used as a fragrance ingredient for its unique fruity, slightly herbaceous, and jasmine-like odor. It is particularly used in the composition of perfumes and fragrances for jasmine, honeysuckle, and lavender scents, adding depth and complexity to the overall aroma.

Preparation

By catalytic reduction of heptylidene cyclopentanone (Arctander, 1969).

Flammability and Explosibility

Nonflammable

Trade name

Fleuramone (IFF), Projasmon P (Symrise）

InChI:InChI=1/C12H22O/c1-2-3-4-5-6-8-11-9-7-10-12(11)13/h11H,2-10H2,1H3

Synthetic route

1-Heptene (592-76-7) + cyclopentanone (120-92-3) → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
With tert.-butylhydroperoxide at 150 - 160℃; under 12000.9 - 13501.1 Torr;	75%
With (t-BuO)2 at 140 - 150℃;	70%
With di-tert-butyl peroxide
With di-tert-butyl peroxide at 140 - 160℃; Autoclave;

2-heptyl-adipic acid (37443-05-3) → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
With acetic anhydride

2-heptylidenecyclopentan-1-one (39189-74-7) → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal
Ir(CO)(PPh3)2Cl at 240℃;

1-heptyl-2-oxo-cyclopentanecarboxylic acid ethyl ester (57138-07-5) → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
With sulfuric acid
Multi-step reaction with 2 steps 1: ethanolic KOH-solution 2: acetic acid anhydride View Scheme

N'-[2-Heptyl-cyclopent-(E)-ylidene]-N,N-dimethyl-hydrazine → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
In tetrahydrofuran; hydrogenchloride; hexane Yield given;

1-heptylidene-cyclopentanone-(2) → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
Hydrogenation;

2-cyclopentylidene-1,1-dimethylhydrazine (14090-60-9) → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, hexane, -5 deg C, 1 h, 2.) THF, hexane, rt, 20 h 2: aq. HCl; tetrahydrofuran; hexane View Scheme

cyclopentanone (120-92-3) + 2-methyl-phenethyl magnesium chloride → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / trifluoroacetic acid; benzene / 5 h / Heating 2: 1.) n-BuLi / 1.) THF, hexane, -5 deg C, 1 h, 2.) THF, hexane, rt, 20 h 3: aq. HCl; tetrahydrofuran; hexane View Scheme

1-Iodoheptane (4282-40-0) → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium ethylate 2: ethanolic KOH-solution 3: acetic acid anhydride View Scheme

heptanal (111-71-7) → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) aq. KOH, (ii) oxalic acid 2: H2 / Pd-C View Scheme
Multi-step reaction with 2 steps 1: (i) benzene, (ii) aq. HCl 2: Ir(CO)(PPh3)2Cl / 240 °C View Scheme

1-Bromoheptane (629-04-9) → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetone / Heating 2: aq. H2SO4 View Scheme

2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetone / Heating 2: aq. H2SO4 View Scheme

heptanal (111-71-7) + cyclopentanone (120-92-3) → 2-heptylcyclopentanone (137-03-1)

Conditions	Yield
With hydrogen at 140℃; under 26252.6 Torr; for 6.66667h; Autoclave;	71 %Chromat.

2-heptylcyclopentanone (137-03-1) → 5-dodecanolide (713-95-1)

Conditions	Yield
With sodium hydrogencarbonate; magnesium monoperoxyphthalate hexahydrate In methanol; water for 24h; Ambient temperature;	98%
With dihydrogen peroxide; tungsten(VI) oxide In acetonitrile at 40℃; for 12h; Time; Reagent/catalyst;	92%
With dihydrogen peroxide; lithium acetate In water; Ethyl propionate at 110℃; for 6h; Baeyer-Villiger Oxidation; Heating / reflux;	91%

2-heptylcyclopentanone (137-03-1) + dibenzyl azodicarboxylate (2449-05-0) → dibenzyl (S)-1-(1-heptyl-2-oxocyclopentyl)hydrazine-1,2-dicarboxylate

Conditions	Yield
With (S)-3,3'-bis(9-anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate In acetonitrile at 20℃; for 48h; enantioselective reaction;	88%

2-heptylcyclopentanone (137-03-1) → 5-dodecanolide (713-95-1) + 5-oxododecanoic acid (3637-16-9) + 5-hydroxydodecanoic acid (7779-95-5)

Conditions	Yield
With water; dihydrogen peroxide at 40℃; for 12h; Reagent/catalyst; Baeyer-Villiger Ketone Oxidation;	A 81% B n/a C n/a

propylene glycol (57-55-6) + 2-heptylcyclopentanone (137-03-1) → 2-methyl-6-heptyl-1,4-dioxaspiro[4.4]nonane (1337968-36-1)

Conditions	Yield
With P0.17Mo2.4CoBr0.27O6.8 In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 6h;	80%
With GdPO4*(MoO2)0.5PMo12O40 In toluene Reflux; Dean-Stark;	80%

2-heptylcyclopentanone (137-03-1) + N-butylamine (109-73-9) → N-butylimino-2-heptylcyclopentane (134852-97-4)

Conditions	Yield
In benzene Heating;	78%

2-heptylcyclopentanone (137-03-1) → δ-dodecalactone (59726-51-1)

Conditions	Yield
With dihydrogen peroxide; molybdenum(VI) oxide In water at 40℃; for 12h; Reagent/catalyst; Baeyer-Villiger Ketone Oxidation;	78%

2-heptylcyclopentanone (137-03-1) → 5-dodecanolide (713-95-1) + δ-dodecalactone (59726-51-1)

Conditions	Yield
With Calcium tetrakis(pentafluorophenyl)borate; dihydrogen peroxide; oxalic acid In water; 1,2-dichloro-ethane at 50℃; for 10h; Reagent/catalyst;	A 65% B 23%

2-heptylcyclopentanone (137-03-1) + ethylene glycol (107-21-1) → 6-heptyl-1,4-dioxaspiro[4.4]nonane (1337968-22-5)

Conditions	Yield
With chlorinated KU-23 In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 6h;	64%
With GdPO4*(MoO2)0.5PMo12O40 In toluene Reflux; Dean-Stark;	54.7%

2-heptylcyclopentanone (137-03-1) + 4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)-5-oxododecanamide

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine; trifluorormethanesulfonic acid; oxygen In m-xylene at 130℃; under 760.051 Torr; for 6h; Sealed tube;	61%

1.3-butanediol (18826-95-4, 107-88-0) + 2-heptylcyclopentanone (137-03-1) → 1-heptyl-7-methyl-6,10-dioxaspiro[4.5]decane (1337968-37-2)

Conditions	Yield
With P0.17Mo2.4CoBr0.27O6.8 In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 6h;	59%

2-heptylcyclopentanone (137-03-1) + benzyl alcohol (100-51-6) → benzyl 5-oxododecanoate

Conditions	Yield
With sulfuric acid; aurin; oxygen In toluene at 20℃; for 24h; Schlenk technique; Irradiation;	47%

2-heptylcyclopentanone (137-03-1) + ethyl 2-cyanoacetate (105-56-6) → ethyl cyano(2-heptylcyclopentylidene)ethanoate

Conditions	Yield
With ammonium acetate; acetic acid In toluene for 90h; Knoevenagel Condensation; Reflux; Dean-Stark;	37%

1,2-diphenyl-2-methylthio-1-ethanone (32368-19-7) + 2-heptylcyclopentanone (137-03-1) → 2-heptyl-2-(methylthio)cyclopentanone (1287312-99-5) + (2RS,5RS)-2-heptyl-5-(methylthio)cyclopentanone + (2RS,5SR)-2-heptyl-5-(methylthio)cyclopentanone

Conditions	Yield
With hydridotetakis(triphenylphosphine)rhodium(I); Dimethyldisulphide; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 90℃; for 3h; Inert atmosphere; regioselective reaction;	A 30% B 5% C 13%

2-heptylcyclopentanone (137-03-1) → 2-heptyl-2-cyclopenten-1-one (37172-74-0) + (E)-2-n-heptylidenecyclopentanone (39189-74-7)

Conditions	Yield
With iron(III) chloride In ethanol; water for 2.5h; Heating;	A 25% B n/a

2-heptylcyclopentanone (137-03-1) + 2-methoxymethylpyrrolidine (76946-27-5) → 2-[2-(methoxymethyl)pyrrolidin-1-yl]-3-heptylcyclopent-2-en-1-one

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 120h; Reflux; Dean-Stark;	11%

Upstream product

• 4282-40-0 1-Iodoheptane 
• 111-71-7 heptanal 
• 120-92-3 cyclopentanone 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 629-04-9 1-Bromoheptane 
• 14090-60-9 2-cyclopentylidene-1,1-dimethylhydrazine 
• 592-76-7 1-Heptene 
• 57138-07-5 1-heptyl-2-oxo-cyclopentanecarboxylic acid ethyl ester 
• 39189-74-7 2-heptylidenecyclopentan-1-one 
• 37443-05-3 2-heptyl-adipic acid 

Downstream Products

• 165385-93-3 2-n-Heptyl cyclopentanone oxime 
• 713-95-1 5-dodecanolide 
• 3637-16-9 5-oxododecanoic acid 
• 7779-95-5 5-hydroxydodecanoic acid 
• 59726-51-1 δ-dodecalactone 
• 165385-93-3 2-heptylcyclopentanoneoxime 
• 37172-74-0 2-heptyl-2-cyclopenten-1-one 
• 39189-74-7 (E)-2-n-heptylidenecyclopentanone 

Relevant articles and documents

One-pot synthesis of 2-alkyl cycloketones on bifunctional Pd/ZrO2 catalyst

2-Alkyl cycloketones are essential chemicals and intermediates for synthetic perfumes and pesticides, which are conventionally produced by multistep process including aldol condensation, separation and hydrogenation. In present work, a batch one-pot cascade approach using aldehydes and cycloketones as the raw materials, and a bifunctional Pd/ZrO2 catalyst was developed for the synthesis of 2-alkyl cycloketones, e.g., cyclohexanone and cycloheptanone. Very high aldehydes (except for paraldehyde with large steric hindrance) conversion and high yields for 2-alkyl cycloketones (e.g., 99 % of conversion for n-butanal and 76 wt.% of yield for 2-butyl cyclohexanone) were obtained at mild temperature of 140 °C. After 10 cycles of reuse, Pd/ZrO2 catalyst showed slight deactivation (ca. 5 % conversion and 10 % yield losses), due to the coke on the catalyst. However, the performance of the catalyst was completely recovered after an oxidative regeneration.

Kinetic Patterns of Condensation of Alkyl- and Cycloalkylcyclopentanones with Dihydric Alcohols in the Presence of Polyoxomolybdate Modified with Oxides of Rare-Earth Elements

The results of condensation of C5–C7 alkyl- and cycloalkyl-substituted cyclopentanones with diatomic vicinal alcohols in the presence of polyoxomolybdate modified with gadolinium oxide are considered. Kinetic patterns are investigated and a kinetic model of the process is proposed. It was established that alkyl- and cycloalkyl derivatives of dioxaspironone are formed directly by two parallel-consecutive routes and through the stages of the preparation of the corresponding hemiacetal. The ratio of the rate constants of these routes depends on the composition and structure of the starting ketones and diols.

Serine carbonates

Serine carbonates of formula I are precursors for organoleptic compounds, masking agents and antimicrobial agents. Further they are alternative substrates for malodor producing enzymes. The symbols in formula I are defined in claim 1.

Compounds having protected hydroxy groups

The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.

Compounds having protected hydroxy groups

The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.

Precursors for fragrant ketones and fragrant aldehydes

The present invention refers to fragrance precursors of formula I for a fragrant ketone of formula II and one or more fragrant aldehydes or ketones of formula III and IV, These fragrance precursors are useful in perfumery, especially in the fine and functional perfumery.

Beta-ketoester compounds

The beta-ketoesters of formula I are useful as precursors for organoleptic compounds, especially for flavors, fragrances and masking agents and antimicrobial compounds.

Ketone precursors for organoleptic compounds

The invention discloses ketones of formula I: wherein, Y is an optionally substituted alkyl, cycloalkyl, or cycloalkylalkyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated; R1is hydrogen or a C1-6alkyl group that is substituted, saturated or unsaturated, straight or branched; A is a chromophoric substituted aromatic ring or ring system; n is an integer; and with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone. These compositions are useful for the delivery of organoleptic compounds, especially of flavors, fragrances, masking agents and antimicrobial compounds.

Catalytic oxidation of alkyl- and cycloalkylcyclanones into lactones

Pilot-plant syntheses of alkyl and cycloalkylcyclanones and their subsequent liquid-phase oxidation into lactones are described. Characteristics of resulting intermediates and target products are reported.