3603-99-4

Basic information

• Product Name: cyclotetradecan-1-one
• Synonyms: cyclotetradecan-1-one;CYCLOTETRADECANONE;Cyclotetradecane-1-one;Einecs 222-758-3
• CAS NO: 3603-99-4
• Molecular Formula: C₁₄H₂₆O
• Molecular Weight: 210.35564
• EINECS: 222-758-3
• Mol File: 3603-99-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 52 °C
• Boiling Point: 302.7 °C at 760 mmHg
• Flash Point: 129.3 °C
• Appearance: /
• Density: 0.859 g/cm³
• Vapor Pressure: 0.000975mmHg at 25°C
• Refractive Index: 1.441
• CAS DataBase Reference: cyclotetradecan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: cyclotetradecan-1-one(3603-99-4)
• EPA Substance Registry System: cyclotetradecan-1-one(3603-99-4)

Safety Data

• Hazardous Substances Data: 3603-99-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 108, p. 2787, 1986 DOI: 10.1021/ja00270a066

Purification Methods

Cyclotetradecanone [3603-99-4] M 206.3, m 25o, b 145o/10mm, d 4 0.926, n D 1.480. It is converted to the semicarbazone which is recrystallised from EtOH and re-converted to the free cyclotetradecanone by hydrolysis [Dretloff et al. J Am Chem Soc 109 7797 1987]. Fractionate it in a vacuum.

InChI:InChI=1/C14H26O/c15-14-12-10-8-6-4-2-1-3-5-7-9-11-13-14/h1-13H2

Upstream product

• 886-42-0 15-thia-bicyclo[10.2.1]pentadeca-12,14-dien-2-one 
• 3661-77-6 cycloheptadecanone 
• 2550-52-9 cyclohexadecanone 
• 1370649-97-0 methyl (1Z)-cyclopentadec-1-ene-1-carboxylate 
• 1370649-96-9 methyl (1Z)-cyclotetradec-1-ene-1-carboxylate 
• 1333501-89-5 methyl (1Z)-cyclohexadec-1-ene-1-carboxylate 
• 58643-74-6 ethyl 2-oxocyclotridecanecarboxylate 
• 832-10-0 cyclotridecanone 
• 878-13-7 cycloundecanone 
• 3350-30-9 cyclononanone 
• 25769-05-5 1-(N-pyrrolidino)-1-cyclododecene 
• 101999-60-4 14-bromo-1-tetradecen-3-one 
• 101999-67-1 14-bromo-1-tetradecen-3-ol 
• 81819-07-0 12-bromo-1-dodecaldehyde 

Downstream Products

• 821-38-5 1,14-tetradecanedioic acid 
• 295-17-0 cyclotetradecane 
• 1502-06-3 cyclodecanone 
• 878-13-7 cycloundecanone 
• 832-10-0 cyclotridecanone 
• 63134-81-6 methyl (1Z)-cycloundec-1-ene-1-carboxylate 
• 830-13-7 cyclododecanone 
• 502-72-7 cyclopentadecanone 
• 84201-29-6 (E)-1-Phenylmethanesulfonyl-cyclotetradecene 
• 84201-29-6 (E)-1-Phenylmethanesulfonyl-cyclotetradecene 
• 84201-16-1 2-Bromo-2-phenylmethanesulfonyl-cyclopentadecanone 
• 84201-20-7 2-Bromo-15-phenylmethanesulfonyl-cyclopentadecanone 
• 75143-11-2 2-[(E)-3-(Methyl-phenyl-amino)-prop-2-en-(Z)-ylidene]-cyclotetradecanone 
• 84201-11-6 2-Phenylmethanesulfonyl-cyclopentadecanone 

Relevant articles and documents

Synthesis of bridged nicotinates having [n](2,5)pyridinophane skeletons (n=8-14)

Synthesis of various bridged nicotinates 6 having [n](2,5)pyridinophane skeletons (n=8-14) was accomplished by the unique pyridine-formation reaction of methyl propiolate with a series of formyl-substituted (vinylimino)phosphoranes 5, which were prepared from the corresponding cycloalkanones 1 via Vilsmeier-Haack formylation giving chloro-substituted cycloalkenals 2, their thermal and photochemical transformation to formyl azirines 4, and the following ring-opening reactions with triphenylphosphine. The HPLC analysis of [11](2,5)pyridinophane derivatives, (Sp,S)-14 and (Rp,S)-14, showed that these diastereomers rapidly epimerize themselves at room temperature and that their planar-chirality was thermodynamically less stable as compared to the corresponding [11](2,5)cyclophane systems.

Exaltone (=Cyclopentadecanone) from Isomuscone (=Cyclohexadecanone), a one-C-atom ring-contraction methodology via a stereospecific favorskii rearrangement: Regioselective application to (-)-(R)-muscone

Treatment of cyclohexadecanone (1g; with I2 (2.2 mol-euqiv.) and KOH in MeOH) furnished the unsaturated (Z)-ester 2g in 83% yield, via a stereospecific Favorskii rearrangement (Scheme 1). Further treatment with 3-chloroperbenzoic acid (m-CPBA) afforded the unreported epoxy ester 3g (88% yield), which was cleaved in 33% yield to Exaltone (=cyclopentadecanone; 1f) with NaOH in MeOH/H2O and then HCl at 65°. This methodology was similarly extended to higher (C17) and lower (C15 to C11) cyclic ketone analogues, as well as regioselectively to (-)-(R)-muscone (5c) and homomuscone (5f) (Scheme 2). Olfactive properties of the corresponding macrocyclic 1-oxaspiro[2,n]alkanes and -alkenes 4 and 8, resulting from a Coreyi-Chaykovsky oxiranylation, are also presented. Copyright

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.