{{Chembox | Watchedfields = changed | verifiedrevid = 460110237 | ImageFile = Cycloheptanone.svg | ImageSize = 100px | PIN = Cycloheptanone | OtherNames = Suberone |Section1={{Chembox Identifiers | CASNo = 502-42-1 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = QH80295937 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 18607 | PubChem = 10400 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 9971 | EINECS = 207-937-6 | SMILES = O=C1CCCCCC1 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C7H12O/c8-7-5-3-1-2-4-6-7/h1-6H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = CGZZMOTZOONQIA-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=7 | H=12 | O=1 | Appearance = Colorless liquid | Density = 0.949 g/cm<sup>3</sup> (20 °C)<ref name=Merck>''The Merck Index'', 11th Edition, '''2728'''</ref> | MeltingPt = | BoilingPtC = 179 to 181 | BoilingPt_ref = <ref name=Merck/> | Solubility = Insoluble }} |Section3={{Chembox Hazards | MainHazards = | FlashPtC = 56 | FlashPt_ref = <ref name=Aldrich>[http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=C99000|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Cycloheptanone] at Sigma-Aldrich</ref> | AutoignitionPt = | GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|226|302|318}} | PPhrases = {{P-phrases|210|233|240|241|242|243|264|270|280|301+312|303+361+353|305+351+338|310|330|370+378|403+235|501}} }} |Section8={{Chembox Related | OtherFunction_label = cyclic ketones | OtherAnions = | OtherCations = | OtherCompounds = | OtherFunction = Cyclohexanone, Cyclooctanone, Tropinone }} }} '''Cycloheptanone''', (CH<sub>2</sub>)<sub>6</sub>CO, is a cyclic ketone also referred to as '''suberone'''. It is a colourless volatile liquid. Cycloheptanone is used as a precursor for the synthesis of pharmaceuticals.
== Synthesis == In 1836, French chemist Jean-Baptiste Boussingault first synthesized cycloheptanone from the calcium salt of dibasic suberic acid. The ketonization of calcium suberate yields calcium carbonate and suberone:<ref>{{ cite book | author = Thorpe, T. E. | title = A Dictionary of Applied Chemistry | year = 1912 | lccn = 12009914 }}</ref> :Ca(O<sub>2</sub>C(CH<sub>2</sub>)<sub>6</sub>CO<sub>2</sub>) → CaCO<sub>3</sub> + (CH<sub>2</sub>)<sub>6</sub>CO
Cycloheptanone is still produced by the cyclization and decarboxylation of suberic acid or suberic acid esters. This reaction is typically conducted in the gas phase at 400–450 °C over alumina doped with zinc oxide or cerium oxide.<ref name="ketones">{{ Ullmann | author = Siegel, H. | author2 = Eggersdorfer, M. | title = Ketones | doi = 10.1002/14356007.a15_077 }}</ref>
Cycloheptanone is also produced by the reaction of cyclohexanone with sodium ethoxide and nitromethane. The resulting sodium salt of 1-(nitromethyl)cyclohexanol is added to acetic acid and shaken with hydrogen gas in the presence of W-4 Raney nickel catalyst. Sodium nitrite and acetic acid are then added to give cycloheptanone.<ref name="organic syntheses">{{ OrgSynth | prep = cv4p0221 | author = Dauben, H. J. Jr. | author2 = Ringold, H. J. | author3 = Wade, R. H. | author4 = Pearson, D. L. | author5 = Anderson, A. G. Jr. | title = Cycloheptanone | year = 1954 | volume = 34 | pages = 19 | collvol = 4 | collvolpages = 221 }}</ref>
Cycloheptanone is also prepared by ring expansion of cyclohexanone with diazomethane as the methylene source.<ref name="organic syntheses"/>
== Uses and reactions == Cycloheptanone is a precursor to bencyclane, a spasmolytic agent and vasodilator.<ref name="ketones" /> Pimelic acid is produced by the oxidative cleavage of cycloheptanone.<ref>{{ Ullmann | author = Cornils, B. | author2 = Lappe, P. | title = Dicarboxylic Acids, Aliphatic | doi = 10.1002/14356007.a08_523.pub2 }}</ref> Dicarboxylic acids such as pimelic acid are useful for the preparation of fragrances and certain polymers.<ref>{{cite web | title = Dicarboxylic Acids | url = http://www.cyberlipid.org/fa/acid0004.htm | publisher = cyberlipids.org | access-date = 2011-04-26 | archive-url = https://web.archive.org/web/20110907093548/http://www.cyberlipid.org/fa/acid0004.htm | archive-date = 2011-09-07 | url-status = dead }}</ref>
Several microorganisms, including ''Mucor plumbeus'', ''Mucor racemosus'', and ''Penicillium chrysogenum'', have been found to reduce cycloheptanone to cycloheptanol. These microorganisms have been investigated for use in certain stereospecific enzymatic reactions.<ref>{{ cite journal |author1=Lemiere, G. L. |author2=Alderweireldt, F. C. |author3=Voets, J. P. | title = Reduction of cycloalkanones by several microorganisms | journal = Zeitschrift für Allgemeine Mikrobiologie | year = 1975 | volume = 15 | issue = 2 | pages = 89–92 | doi = 10.1002/jobm.19750150204 }}</ref>
==References== {{Reflist}}
7 Category:Seven-membered rings