| Revision as of 19:49, 29 April 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits Added StdInChIKey← Previous edit |
Latest revision as of 14:10, 25 August 2023 edit undoJWBE (talk | contribs)Extended confirmed users10,127 edits →References: +cat |
| (49 intermediate revisions by 36 users not shown) |
| Line 1: |
Line 1: |
|
{{Chembox |
|
{{Chembox |
|
|
| Watchedfields = changed |
|
|
| verifiedrevid = 460110237 |
|
| ImageFile = Cycloheptanone.svg |
|
| ImageFile = Cycloheptanone.svg |
|
| ImageSize = 100px |
|
| ImageSize = 100px |
|
| IUPACName = Cycloheptanone |
|
| PIN = Cycloheptanone |
|
| OtherNames = Suberone |
|
| OtherNames = Suberone |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| CASNo = 502-42-1 |
|
| CASNo = 502-42-1 |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| PubChem = 10400 |
|
|
|
| UNII = QH80295937 |
| ⚫ |
| ChemSpiderID = 9971 |
|
|
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
| ⚫ |
| SMILES = O=C1CCCCCC1 |
|
|
|
| ChEMBL = 18607 |
| ⚫ |
| StdInChI=1S/C7H12O/c8-7-5-3-1-2-4-6-7/h1-6H2 |
|
|
⚫ |
| PubChem = 10400 |
| ⚫ |
| StdInChIKey = CGZZMOTZOONQIA-UHFFFAOYSA-N |
|
|
|
| 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 |
|
|Section2={{Chembox Properties |
|
| C=7|H=12|O=1 |
|
| C=7 | H=12 | O=1 |
|
| Appearance = Colorless liquid |
|
| Appearance = Colorless liquid |
|
| Density = 0.949 g/cm<sup>3</sup> (20 °C)<ref name=Merck>'']'', 11th Edition, '''2728'''</ref> |
|
| Density = 0.949 g/cm<sup>3</sup> (20 °C)<ref name=Merck>'']'', 11th Edition, '''2728'''</ref> |
|
| MeltingPt = |
|
| MeltingPt = |
|
| BoilingPt = 179-181 °C<ref name=Merck/> |
|
| BoilingPtC = 179 to 181 |
|
|
| BoilingPt_ref = <ref name=Merck/> |
|
| Solubility = Insoluble |
|
| Solubility = Insoluble |
|
}} |
|
}} |
|
| Section3 = {{Chembox Hazards |
|
|Section3={{Chembox Hazards |
|
| MainHazards = |
|
| MainHazards = |
|
|
| FlashPtC = 56 |
|
| FlashPt = 56 °C<ref name=Aldrich> at ]</ref> |
|
| FlashPt_ref = <ref name=Aldrich> at ]</ref> |
|
| Autoignition = |
|
|
|
| AutoignitionPt = |
|
| RPhrases = {{R41}}<ref name=Aldrich/> |
|
|
| SPhrases = {{S23}} {{S24/25}} {{S26}} {{S39}}<ref name=Aldrich/> |
|
| 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 |
|
|Section8={{Chembox Related |
|
| Function = ]s |
|
| OtherFunction_label = ]s |
|
| OtherAnions = |
|
| OtherAnions = |
|
| OtherCations = |
|
| OtherCations = |
|
| OtherCpds = |
|
| OtherCompounds = |
|
| OtherFunctn = ], ], ] }} |
|
| OtherFunction = ], ], ] }} |
|
}} |
|
}} |
|
'''Cycloheptanone''', (CH<sub>2</sub>)<sub>6</sub>CO, is a ] also referred to as '''suberone'''. It is a colourless volatile liquid. Cycloheptanone is used as a precursor for the synthesis of pharmaceuticals. |
|
'''Cycloheptanone''', (CH<sub>2</sub>)<sub>6</sub>CO, is a ] also referred to as '''suberone'''. It is a colourless volatile liquid. Cycloheptanone is used as a precursor for the synthesis of pharmaceuticals. |
|
|
|
|
|
== Synthesis == |
|
== Synthesis == |
|
In 1836, French chemist Jean-Baptiste Boussingault first synthesized cycloheptanone from the calcium salt of dibasic suberic acid. The ] of calcium suberate yields calcium carbonate and suberone:<ref>Thorpe, T. E.; A dictionary of applied chemistry. 1912.</ref> |
|
In 1836, French chemist ] first synthesized cycloheptanone from the calcium salt of dibasic ]. The ] 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 |
|
: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.; Eggersdorfer, M. | title = Ketones | doi = 10.1002/14356007.a15_077}}</ref> |
|
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 ] and ]. The resulting sodium salt of 1-(nitromethyl)cyclohexanol is added to ] and shaken with hydrogen gas in the presence of W-4 ] catalyst. ] and acetic acid are then added to give cycloheptanone.<ref name="organic syntheses">{{OrgSynth | prep = cv4p0221 | author = Hyp J. Dauben, Jr., Howard J. Ringold, Robert H. Wade, David L. Pearson, and Arthur G. Anderson, Jr. | title = Cycloheptanone | collvol = 4 | collvolpages = 221 | year = 1963 }}</ref> |
|
Cycloheptanone is also produced by the reaction of cyclohexanone with ] and ]. The resulting sodium salt of 1-(nitromethyl)cyclohexanol is added to ] and shaken with hydrogen gas in the presence of W-4 ] catalyst. ] 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 ] with ] as the methylene source.<ref name="organic syntheses"/> |
|
Cycloheptanone is also prepared by ring expansion of ] with ] as the methylene source.<ref name="organic syntheses"/> |
|
|
|
|
|
== Uses and reactions == |
|
== Uses and reactions == |
|
Cycloheptanone has no direct applications, but is is a precursor to other compounds. ], a spasmolytic agent and vasodilator is produced from it, for example.<ref name="ketones" /> ] is produced by the oxidative cleavage of cycloheptanone.<ref>{{Ullmann | author = Cornils, B.; 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>Dicarboxylic Acids. http://www.cyberlipid.org/fa/acid0004.htm</ref> |
|
Cycloheptanone is a precursor to ], a spasmolytic agent and vasodilator.<ref name="ketones" /> ] 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> ]s such as ] 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>Lemiere, G. L.; Alderweireldt, F. C.; Voets, J. P.; “Reduction of cycloalkanones by several microorganisms” Zeitschrift für Allg. Mikrobiologie, 1975. 15 (2), pp 89-92. DOI: 10.1002/jobm.19750150204</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== |
|
==References== |
|
{{reflist}} |
|
{{Reflist}} |
|
|
|
|
|
] |
|
] |
|
|
] |
|
|
|
|
] |
|