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{{Chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 442644805 | 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_Ref = {{chemspidercite|correct|chemspider}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 18607
⚫ | PubChem = 10400
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9971 | ChemSpiderID = 9971
| SMILES = O=C1CCCCCC1 | EINECS = 207-937-6
| SMILES = O=C1CCCCCC1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=1S/C7H12O/c8-7-5-3-1-2-4-6-7/h1-6H2 | StdInChI = 1S/C7H12O/c8-7-5-3-1-2-4-6-7/h1-6H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CGZZMOTZOONQIA-UHFFFAOYSA-N | 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&nbsp;°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&nbsp;°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 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> ]s such as ] 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}}


] ]
]

]
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Latest revision as of 14:10, 25 August 2023

Cycloheptanone
Names
Preferred IUPAC name Cycloheptanone
Other names Suberone
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.216 Edit this at Wikidata
EC Number
  • 207-937-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H12O/c8-7-5-3-1-2-4-6-7/h1-6H2Key: CGZZMOTZOONQIA-UHFFFAOYSA-N
SMILES
  • O=C1CCCCCC1
Properties
Chemical formula C7H12O
Molar mass 112.172 g·mol
Appearance Colorless liquid
Density 0.949 g/cm (20 °C)
Boiling point 179 to 181 °C (354 to 358 °F; 452 to 454 K)
Solubility in water Insoluble
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H226, H302, H318
Precautionary statements P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P312, P303+P361+P353, P305+P351+P338, P310, P330, P370+P378, P403+P235, P501
Flash point 56 °C (133 °F; 329 K)
Related compounds
Related cyclic ketones Cyclohexanone, Cyclooctanone, Tropinone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Cycloheptanone, (CH2)6CO, 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:

Ca(O2C(CH2)6CO2) → CaCO3 + (CH2)6CO

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.

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.

Cycloheptanone is also prepared by ring expansion of cyclohexanone with diazomethane as the methylene source.

Uses and reactions

Cycloheptanone is a precursor to bencyclane, a spasmolytic agent and vasodilator. Pimelic acid is produced by the oxidative cleavage of cycloheptanone. Dicarboxylic acids such as pimelic acid are useful for the preparation of fragrances and certain polymers.

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.

References

  1. ^ The Merck Index, 11th Edition, 2728
  2. Cycloheptanone at Sigma-Aldrich
  3. Thorpe, T. E. (1912). A Dictionary of Applied Chemistry. LCCN 12009914.
  4. ^ Siegel, H.; Eggersdorfer, M. "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3-527-30673-2.
  5. ^ Dauben, H. J. Jr.; Ringold, H. J.; Wade, R. H.; Pearson, D. L.; Anderson, A. G. Jr. (1954). "Cycloheptanone". Organic Syntheses. 34: 19; Collected Volumes, vol. 4, p. 221.
  6. Cornils, B.; Lappe, P. "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523.pub2. ISBN 978-3-527-30673-2.
  7. "Dicarboxylic Acids". cyberlipids.org. Archived from the original on 2011-09-07. Retrieved 2011-04-26.
  8. Lemiere, G. L.; Alderweireldt, F. C.; Voets, J. P. (1975). "Reduction of cycloalkanones by several microorganisms". Zeitschrift für Allgemeine Mikrobiologie. 15 (2): 89–92. doi:10.1002/jobm.19750150204.
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