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

• 1119-79-5 pentadecanedioic acid diethyl ester 
• 3603-98-3 2-Oxocyclotetradecancarbonsaeure-methylester 
• 886-42-0 15-thia-bicyclo[10.2.1]pentadeca-12,14-dien-2-one 
• 186581-53-3 diazomethane 
• 832-10-0 cyclotridecanone 
• 830-13-7 cyclododecanone 
• 14108-91-9 1,2-Cyclotetradecadien 
• 7677-24-9 trimethylsilyl cyanide 
• 78845-09-7 cyclotetradeca-3,5,7-trien-1-one 
• 101999-60-4 14-bromo-1-tetradecen-3-one 
• 101999-61-5 14-iodo-1-tetradecen-3-one 
• 69297-60-5 2-ethoxycarbonyl-1-cyclotetradecanone 
• 6244-49-1 1-vinyl-1-cyclododecanol 
• 54561-32-9 2-oxocyclotetradecanol 

Downstream Products

• 821-38-5 1,14-tetradecanedioic acid 
• 295-17-0 cyclotetradecane 
• 95784-87-5 2-methylenecyclotetradecanone 
• 75143-09-8 2-[(E)-3-Dimethylamino-prop-2-en-(Z)-ylidene]-cyclotetradecanone 
• 927-63-9 3-dimethylaminoacrolein 
• 84201-11-6 2-Phenylmethanesulfonyl-cyclopentadecanone 
• 75143-11-2 2-[(E)-3-(Methyl-phenyl-amino)-prop-2-en-(Z)-ylidene]-cyclotetradecanone 
• 84201-20-7 2-Bromo-15-phenylmethanesulfonyl-cyclopentadecanone 
• 84201-16-1 2-Bromo-2-phenylmethanesulfonyl-cyclopentadecanone 
• 84201-29-6 (E)-1-Phenylmethanesulfonyl-cyclotetradecene 
• 84201-29-6 (E)-1-Phenylmethanesulfonyl-cyclotetradecene 
• 1502-06-3 cyclodecanone 
• 878-13-7 cycloundecanone 
• 832-10-0 cyclotridecanone 

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 novel, short and repeatable two-carbon ring expansion reaction by thermo-isomerization: Easy synthesis of macrocyclic ketones

A novel two-carbon ring enlargement procedure, in which medium- and large-ring 1-vinylcycloalkanols are thermoisomerized in a flow reactor system at temperatures of 600°C to about 650°C, produces the isomeric ring-expanded cycloalkanones directly and efficiently. This two-step ring expansion protocol can easily be applied several times successively. For e.g., the musk odorant cyclopentadecanone (Exaltone?) is prepared from cycloundecanone in two repetitive cycles. Thermo-isomerization of the corresponding ethynylic cycloalkanols gives in moderate yields the bishomologous α,β-unsaturated macrocyclic (E)-2-cycloalkenones. A reaction mechanism via alkyl hydroxyallyl biradical intermediates is proposed.