1,2-二氧雜環戊烷
1,2-二氧雜環戊烷，別名1,2-二氧戊環、1,2-二氧五環等，是一種化合物，分子式為C3H6O2，由三個碳原子和相鄰位置的兩個氧原子組成的環組成。其結構式可寫為[–(CH2)3–O–O–]。[1][2]
| 1,2-二氧雜環戊烷 | |
|---|---|
| |
| IUPAC名 1,2-Dioxolane 1,2-二氧戊環 | |
| 系統名 1,2-Dioxacyclopentane 1,2-二氧雜環戊烷 | |
| 別名 | 1,2-二氧五環 1,2-二噁環戊烷 |
| 識別 | |
| CAS號 | 4362-13-4 
|
| PubChem | 138198 |
| ChemSpider | 121835 |
| SMILES |
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| 性質 | |
| 化學式 | C3H6O2 |
| 摩爾質量 | 74.08 g·mol−1 |
| 若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。 | |
合成
1,2-二氧戊環核心結構的合成方法包括用單線態氧[3]或分子氧與合適的催化劑氧化環丙烷衍生物、[4][5]使用自動氧化、過氧化氫進行親核置換，並用硝酸汞處理、擴展π-系統的光解、[6]雙甲硅烷基過氧化物與烯烴的反應，[7]或與2-過羥基4-烯烴與二乙胺[8]或乙酸汞的反應。[9][10]
出現
一些衍生物存在於自然界，例如在Calophyllum dispar和馬米杏的種子。[6]Plakinic acid A和類似化合物是從Plakortis的海綿中分離出來的。[11][12]甘松新酮是一種含有1,2-二氧戊環的倍半萜衍生物，從名為Adenosma caeruleum的植物中分離出來。[13]
用途
合成和天然的二氧戊環衍生物已被用作或被認為是抗瘧藥。[6][7]Plakinic acid A和相關化合物顯示出抗真菌作用。[11]
參見
參考資料
- ^ Lay TH, Bozzelli JW. Enthalpies of formation of cyclic alkyl peroxides: Dioxirane, 1,2-dioxetane, 1,2-dioxolane, and 1,2-dioxane. Chemical Physics Letters. 199, 268 (1–2): 175–179. Bibcode:1997CPL...268..175L. doi:10.1016/S0009-2614(97)00168-1.
- ^ Demaison J. 2.5.2.5 Elements with two or three internal rotors. Diamagnetic Molecules. Landolt-Börnstein - Group II Molecules and Radicals 14a. 1982: 415–425. ISBN 3-540-11365-7. doi:10.1007/10201404_40.
- ^ Akasaka T, Fukuoka K, Ando W. Formation of 1,2-dioxolane in the singlet oxygenation of cyclopropane. Tetrahedron Letters. 1991, 32 (52): 7695–7698. doi:10.1016/0040-4039(91)80568-Q.
- ^ Feldman KS, Simpson RE. Stereochemical studies on the preparation and subsequent reductive cleavage of 1,2-dioxolanes. Application to the synthesis of (±)-yashabushitriol. Tetrahedron Letters. 1989, 30 (50): 6985–6988. doi:10.1016/S0040-4039(01)93404-5.
- ^ Mata S, González J, Vicente R, López LA. Zinc-Catalyzed Multicomponent Reactions: Easy Access to Furyl-Substituted Cyclopropane and 1,2-Dioxolane Derivatives (PDF). European Journal of Organic Chemistry. 2016, 2016 (15): 2681–2687 [2023-04-26]. doi:10.1002/ejoc.201600393. （原始內容存檔 (PDF)於2023-04-26）.
- ^ 6.0 6.1 6.2 Helesbeux JJ, Peyronnet D, Labaïed M, Grellier P, Frappier F, Seraphin D, et al. Synthesis and antimalarial activity of some new 1,2-dioxolane derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry. December 2002, 17 (6): 431–7. PMID 12683680. doi:10.1080/1475636021000005677
.
- ^ 7.0 7.1 Martyn DC, Ramirez AP, Beattie MJ, Cortese JF, Patel V, Rush MA, et al. Synthesis of spiro-1,2-dioxolanes and their activity against Plasmodium falciparum. Bioorganic & Medicinal Chemistry Letters. December 2008, 18 (24): 6521–4. PMID 18993067. doi:10.1016/j.bmcl.2008.10.083.
- ^ Liu HH, Jin HX, Wu YK. Synthesis and cleavage studies of a 1,2-dioxolane-type peroxide. Chinese Journal of Chemistry. 2010, 22 (9): 1029–1033. doi:10.1002/cjoc.20040220930.
- ^ Booldworth AJ, Tallant NA. 1,2,4-Trioxane versus 1,2-dioxolane formation in the mercury(II) acetate-mediated cyclisation of hemiperoxyacetals derived from allylic hydroperoxides. Journal of the Chemical Society, Chemical Communications. 1992, (5): 428. doi:10.1039/C39920000428.
- ^ Bloodworth AJ, Bothwell BD, Collins AN, Maidwell NL. A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group. Tetrahedron Letters. 1996, 37 (11): 1885–1888. doi:10.1016/0040-4039(96)00143-8.
- ^ 11.0 11.1 Phillipson DW, Rinehart Jr K. Antifungal peroxide-containing acids from two Caribbean sponges. Journal of the American Chemical Society. 1983, 105 (26): 7735–7736. doi:10.1021/ja00364a045.
- ^ Dai P, Trullinger TK, Liu X, Dussault PH. Asymmetric synthesis of 1,2-dioxolane-3-acetic acids: synthesis and configurational assignment of plakinic acid A. The Journal of Organic Chemistry. March 2006, 71 (6): 2283–92. PMID 16526775. doi:10.1021/jo0522254.
- ^ Kandur WV, Richert KJ, Rieder CJ, Thomas AM, Hu C, Ziller JW, Woerpel KA. Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones. Organic Letters. May 2014, 16 (10): 2650–3. PMID 24779430. doi:10.1021/ol500835f.
