| 词条 | 3,3,4,4-Tetramethyltetrahydrofuran-2,5-dione |
| 释义 |
| Watchedfields = | verifiedrevid = | ImageFile1 = Tetramethylsuccinic anhydride.svg | ImageSize1 = 150px | IUPACName = 3,3,4,4-Tetramethyloxolane-2,5-dione | OtherNames = Tetrahydro-3,3,4,4-tetramethylfuran-2,5-dione; 3,3,4,4-tetramethyloxolane-2,5-dione; 3,3,4,4-tetramethytetrahydrofuran-2,5-quinone; dihydro-3,3,4,4-tetramethyl-2,5-furandione; tetramethylsuccinic anhydride; TMSA | Section1 = {{Chembox Identifiers | PubChem = 141941 | ChemSpiderID = 125215 | SMILES = CC1(C(=O)OC(=O)C1(C)C)C | StdInChI = 1S/C8H12O3/c1-7(2)5(9)11-6(10)8(7,3)4/h1-4H3 | StdInChIKey = KYZIXHLDWJBHDI-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 35046-68-5 | UNII = | UNII_Ref = {{fdacite|correct|FDA}} | EINECS = | Section2 = {{Chembox Properties | Formula = C8H12O3 | MolarMass = 156.179 | Appearance = White crystalline[1] | Density = 1.044 g/cm3[2] | MeltingPtC = 147 | MeltingPt_notes = [1] | BoilingPtC = 226.1 | BoilingPt_notes = 760mmHg[2]
In chemistry, 3,3,4,4-tetramethyltetrahydrofuran-2,5-dione is a heterocyclic compound with the formula {{chem|C|8|H|12|O|3}}, or (CH3)2(COC2COO)(CH3)2. It is a white crystalline solid with a pungent camphoraceous odor.[1] The compound is also called 3,3,4,4-tetramethyloxolane-2,5-dione (its IUPAC name) or 3,3,4,4-tetramethylsuccinic anhydride,[2] namely the anhydride of 2,2,3,3-tetramethylsuccinic acid, and sometimes abbreviated as TMSA.[3] It can be seen as derivative of tetrahydrofuran-2,5-dione (oxolane-2,5-dione) with two methyl groups replacing two hydrogen atoms on each of the carbon atoms in the ring that are not adjacent to the ring oxygen.[4] Synthesis and chemistryThe compound is soluble in petroleum ether.[1][14] The compound was described in 1890 by Karl von Auwers and Victor Meyer who obtained it by thermal decomposition of 2,2,3,3-tetramethylsuccinic acid.[5][6] It can also be obtained, in > 50% yield, from 3,3,4,4-tetramethylpyrrolidine-2,5-dione [7] Other synthesis routes include
See also
References1. ^?? {{DEFAULTSORT:Tetramethyltetrahydrofuran-2,5-dione, 3,3,4,4-}}2. ^{{Cite web|url=|title=}} 3. ^Subat Turdi, Peisheng Xu, Qun Li, Youqing Shen, Parhat Kerram, and Jun Ren (2008), Amidization of Doxorubicin Alleviates Doxorubicin-Induced Contractile Dysfunction and Reduced Survival in Murine Cardiomyocytes. Toxicology Letters volume 178, issue 3, pages 197–201. {{doi|10.1016/j.toxlet.2008.03.010}} 4. ^1 2 3 4 5 "3,3,4,4-tetramethyloxolane-2,5-dione" at Molbase. Accessed on 2015-08-01. 5. ^1 2 3 4 Karl von Auwers, Victor Meyer (1890), Ueber Tetramethylbernsteinsäure und Trimethylglutarsäure. Berichte der deutschen chemischen Gesellschaft, volume 23, issue 1, pages 293,301,304–305. {{doi|10.1002/cber.18900230151}} 6. ^Karl von Auwers, O. Ungemach (1935) Zur Zerreißbarkeit der Kohlenstoffkette in Bernsteinsäure-Derivaten. Berichte der deutschen chemischen Gesellschaft, volume 68, pages 23, 349–351. {{doi|10.1002/cber.19350680228}} 7. ^1 Snezna Bizilj, David P. Kelly, Algirdas K. Serelis, David H. Solomon, Kathleen E. White (1985). The Self-Reactions of 1-Methoxycarbonyl-1-methylethyl and Higher Ester Radicals: Combination vs Disproportionation and Oligomeric Products from Secondary Reactions. Australian Journal of Chemistry, volume 38, issue 11, pages 1657–1673. {{doi|10.1071/CH9851657}} 8. ^J. Thiele, K. Heuser (1896). Ueber Hydrazinderivate der Isobuttersäure. Justus Liebigs Annalen der Chemie, volume 290, pages 1–43. 9. ^Eugene Rothstein, Charles William Shoppee (1927), Ring-chain tautomerism. Part XV. The hydroxy-lactone type. Journal of the Chemical Society (UK; Resumed), article LXXVIII, pages 531-534. {{doi|10.1039/JR9270000531}}. 1 : Tetrahydrofurans |
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