User:ColinPan1999/sandbox
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| IUPAC名 Cycloheptanone | |
| 别名 | Suberone |
| 识别 | |
| CAS号 | 502-42-1 
|
| PubChem | 10400 |
| ChemSpider | 9971 |
| SMILES |
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| 性质 | |
| 化学式 | C7H12O |
| 摩尔质量 | 112.17 g·mol−1 |
| 外观 | 无色液体 |
| 密度 | 0.949 g/cm3 (20 °C)[1] |
| 沸点 | 179–181 °C[1] |
| 溶解性（水） | 不溶 |
| 危险性 | |
| 警示术语 | R：R41[2] |
| 安全术语 | S：S23 S24/25 S26 S39[2] |
| 闪点 | 56 °C[2] |
| 相关物质 | |
| 相关环酮 | 环己酮, 环辛酮, 托品酮 |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
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
[编辑]In 1836, French chemist Jean-Baptiste Boussingault first synthesized cycloheptanone from the calcium salt of dibasic suberic acid. The destructive distillation of calcium suberate yields calcium carbonate and suberone:[3]
- 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.[4]
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.[5]
Cycloheptanone is also prepared by ring expansion of cyclohexanone with diazomethane as the methylene source.[5]
Uses and reactions
[编辑]Cycloheptanone has no direct applications, but is a precursor to other compounds. Bencyclane, a spasmolytic agent and vasodilator is produced from it, for example.[4] Pimelic acid is produced by the oxidative cleavage of cycloheptanone.[6] Dicarboxylic acids such as pimelic acid are useful for the preparation of fragrances and certain polymers.[7]
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.[8]
References
[编辑]- ^ 1.0 1.1 The Merck Index, 11th Edition, 2728
- ^ 2.0 2.1 2.2 Cycloheptanone at Sigma-Aldrich
- ^ Thorpe, T. E.; A dictionary of applied chemistry. 1912.
- ^ 4.0 4.1 Siegel, H.; Eggersdorfer, M., Ketones, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a15_077
- ^ 5.0 5.1 Hyp J. Dauben, Jr., Howard J. Ringold, Robert H. Wade, David L. Pearson, and Arthur G. Anderson, Jr. (1963). "Cycloheptanone". Org. Synth.; Coll. Vol. 4: 221.
- ^ Cornils, B.; Lappe, P., Dicarboxylic Acids, Aliphatic, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a08_523.pub2
- ^ Dicarboxylic Acids. http://www.cyberlipid.org/fa/acid0004.htm
- ^ 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