| 词条 | Santonic acid |
| 释义 |
| Watchedfields = changed | verifiedrevid = 464387054 | ImageFileL1 =Santonic-acid-2D-skeletal.png | ImageFileR1 = Santonic-acid-from-xtal-3D-balls.png | IUPACName = (−)-2,3,3a,4,5,6,7,7a-octahydro-α,3a,5-trimethyl-6,8-dioxo-1,4-methano-1H-indene-1-acetic acid | OtherNames = |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 249878 | InChI = 1/C15H20O4/c1-7-9(16)6-10-14(3)4-5-15(10,8(2)13(18)19)12(17)11(7)14/h7-8,10-11H,4-6H2,1-3H3,(H,18,19) | InChIKey = UNPYYTKZOHYHMZ-UHFFFAOYAW | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C15H20O4/c1-7-9(16)6-10-14(3)4-5-15(10,8(2)13(18)19)12(17)11(7)14/h7-8,10-11H,4-6H2,1-3H3,(H,18,19) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = UNPYYTKZOHYHMZ-UHFFFAOYSA-N | CASNo = | PubChem = 283654 | SMILES = O=C(O)C(C31C(=O)C2C(C(=O)CC1C2(CC3)C)C)C }} |Section2={{Chembox Properties | Formula = C15H20O4 | MolarMass = 264.32 g mol−1 | Appearance = | Density = 1.184 g cm−3[1] | MeltingPtC = 173 | MeltingPt_ref = [1] | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} Santonic acid is an organic compound containing both carboxylic acid and ketone functionality. It was synthesized from santonin by base-mediated hydrolysis of a lactone followed by a multistep rearrangement process by R. B. Woodward.[2] Unusually for a carboxylic acid, santonic acid does not form hydrogen-bonded dimers in the crystalline phase. Rather, it adopts a polymeric structure, with individual santonic acid molecules linked by intermolecular carboxyl-to-ketone hydrogen bonds.[1] References1. ^1 2 {{ cite journal | journal = Acta Crystallogr. C | volume = 55 | issue = 4 |date=April 1999 | pages = 566–568 | doi = 10.1107/S0108270198014231 | title = Santonic acid: catemeric hydrogen bonding in a γ,ε-diketo carboxylic acid | author = A. P. J. Brunskill, H. W. Thompson and R. A. Lalancette }} {{ketone-stub}}2. ^Reusch, William (1999). "Base-catalyzed rearrangements {{webarchive|url=https://web.archive.org/web/20090207013929/http://www.cem.msu.edu/~reusch/VirtualText/rearang2.htm |date=2009-02-07 }}". In: Virtual Textbook of Organic Chemistry. Michigan State University. Retrieved September 10, 2008. 3 : Ketones|Sesquiterpenes|Propionic acids |
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