1,3-二氧五环

1,3-二氧五环
	IUPAC名; 1,3-Dioxolane
	系统名; 1,3-Dioxacyclopentane
别名	二氧五环; 5-冠-2; 1,3-二氧戊环; 二氧戊环
识别
CAS号	646-06-0
PubChem	12586
ChemSpider	12066
SMILES	O1CCOC1;
InChI	1/C3H6O2/c1-2-4-5-3-1/h1-3H2;
InChIKey	SNQXJPARXFUULZ-UHFFFAOYAS
EINECS	211-463-5
ChEBI	87597
性质
化学式	C3H6O2
摩尔质量	74.08 g·mol⁻¹
外观	挥发性的无色液体
密度	1.06 g/cm3
熔点	-95 °C（178 K）（）
沸点	74 °C（347 K）（）
溶解性（水）	混溶
溶解性	可溶于乙醇、乙醚和丙酮
相关物质
相关化学品	1,2-二氧五环
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

1,3-二氧五环是一种有机化合物，化学式 C
3H
6O
2。

制备

1,3-二氧五环可以由乙二醇和甲醛在酸催化下而成：^[4]

它也可以由环氧乙烷和甲醛在四氯化锡或四乙基溴化铵催化下反应而成。^[5]

性质

物理性质

1,3-二氧五环是一种挥发性的无色液体，沸点 74 °C。^[2]在−97 °C下，1,3-二氧五环会凝固，熔化热6.57 kJ·mol⁻¹。^[6]^[7]1,3-二氧五环有两种同质异形体，其中II型在−131 °C以下产生，转变成I型时会放出2.68 kJ·mol⁻¹的能量。^[7]它混溶于水、乙醚、丙酮和四氢呋喃。^[3]^[5]

化学性质

1,3-二氧五环倾向形成过氧化物。^[3]在酸存在下，1,3-二氧五环容易水解成乙二醇和甲醛，在碱中则比较稳定。当1,3-二氧五环被加热到470 °C 至500 °C时，它会分解成甲酸和乙烯。^[5]它和乙酰溴反应，生成2-(溴甲氧基)乙酸乙酯。^[8]

用处

1,3-二氧五环是生产聚甲醛的共聚物。^[3]

参考资料

^ Front Matter. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014: 145. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.
^ ^2.0 ^2.1 ^2.2 ^2.3 ^2.4 Record of CAS RN 646-06-0 in the GESTIS Substance Database from the IFA（英语：Institute for Occupational Safety and Health）
^ ^3.0 ^3.1 ^3.2 ^3.3 ^3.4 Entry on 1,3-Dioxolan. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
^ von Karl-Heinz Lautetnschläger, Werner Schröter, Andrea Wanninger. Taschenbuch der Chemie – Karl-Heinz Lautenschläger, Werner Schröter, Andrea Wanninger. Harri Deutsch Verlag. 2005: 451. ISBN 978-3-81711760-4.
^ ^5.0 ^5.1 ^5.2 Vishnu Ji Ram; Arun Sethi; Mahendra Nath; Ramendra Pratap: The Chemistry of Heterocycles – Nomenclature and Chemistry of Three-to-Five Membered Heterocycles, Elsevier 2017, ISBN 978-0-08-101033-4.
^ E. S. Domalski, E. D. Hearing: Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III. in : J. Phys. Chem. Ref. Data 25 (1996) 1–525, doi:10.1063/1.555985.
^ ^7.0 ^7.1 Clegg, G.A.; Melia, T.P.: Thermodynamics of polymerization of heterocyclic compounds. Part V. The heat capacity, entropy, enthalpy and free energy of 1,3-dioxolan and poly-1,3-dioxolan in Polymer 10 (1969) 912–922.
^ Silvia Vertuani, Anna Baldisserotto, Katia Varani, Pier Andrea Borea, Bonache De Marcos Maria Cruz, Luca Ferraro, Stefano Manfredini, Alessandro Dalpiaz. Synthesis and in vitro stability of nucleoside 5′-phosphonate derivatives. European Journal of Medicinal Chemistry. 2012-08, 54: 202–209 [2021-08-11]. doi:10.1016/j.ejmech.2012.04.045. （原始内容存档于2018-07-03）（英语）.

[1] Front Matter. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014: 145. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.

[GESTIS-2] 2.0 ^2.1 ^2.2 ^2.3 ^2.4 Record of CAS RN 646-06-0 in the GESTIS Substance Database from the IFA（英语：Institute for Occupational Safety and Health）

[römpp-3] 3.0 ^3.1 ^3.2 ^3.3 ^3.4 Entry on 1,3-Dioxolan. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.

[von_Karl-Heinz_Lautenschläger,_Werner_Schröter,_Andrea_Wanninger-4] von Karl-Heinz Lautetnschläger, Werner Schröter, Andrea Wanninger. Taschenbuch der Chemie – Karl-Heinz Lautenschläger, Werner Schröter, Andrea Wanninger. Harri Deutsch Verlag. 2005: 451. ISBN 978-3-81711760-4.

[Ram-5] 5.0 ^5.1 ^5.2 Vishnu Ji Ram; Arun Sethi; Mahendra Nath; Ramendra Pratap: The Chemistry of Heterocycles – Nomenclature and Chemistry of Three-to-Five Membered Heterocycles, Elsevier 2017, ISBN 978-0-08-101033-4.

[Domalski-6] E. S. Domalski, E. D. Hearing: Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III. in : J. Phys. Chem. Ref. Data 25 (1996) 1–525, doi:10.1063/1.555985.

[Clegg-7] 7.0 ^7.1 Clegg, G.A.; Melia, T.P.: Thermodynamics of polymerization of heterocyclic compounds. Part V. The heat capacity, entropy, enthalpy and free energy of 1,3-dioxolan and poly-1,3-dioxolan in Polymer 10 (1969) 912–922.

[8] Silvia Vertuani, Anna Baldisserotto, Katia Varani, Pier Andrea Borea, Bonache De Marcos Maria Cruz, Luca Ferraro, Stefano Manfredini, Alessandro Dalpiaz. Synthesis and in vitro stability of nucleoside 5′-phosphonate derivatives. European Journal of Medicinal Chemistry. 2012-08, 54: 202–209 [2021-08-11]. doi:10.1016/j.ejmech.2012.04.045. （原始内容存档于2018-07-03）（英语）.

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