| 词条 | Carbomethoxymethylenetriphenylphosphorane |
| 释义 |
| ImageFile = Carbomethoxymethylenetriphenylphosphorane.svg | IUPACName = Methyl 2-(triphenyl-λ5-phosphanylidene)acetate |Section1 = {{Chembox Identifiers | PubChem = 17453 | CASNo = 2605-67-6 | EC_number = 220-018-4 | ChEMBL = 1715161 | StdInChI=1S/C21H19O2P/c1-23-21(22)17-24(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3 | StdInChIKey = NTNUDYROPUKXNA-UHFFFAOYSA-N | SMILES = COC(=O)C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3 }} }} Carbomethoxymethylenetriphenylphosphorane is a chemical compound used in organic syntheses. It contains a phosphorus atom bound to three phenyl groups, and doubly bound to the alpha position of methyl acetate. It undergoes a Wittig reaction.[1] It is used in the Vitamin B12 total synthesis. ProductionCarbomethoxymethylenetriphenylphosphorane can be made via a multistep reaction using bromoacetic acid, dicyclohexylcarbodiimide, and triphenylphosphine. This make a phosphonium salt, which is converted to the final product by sodium carbonate in water.[1] ReactionsCarbomethoxymethylenetriphenylphosphorane reacts with aldehydes to give a two carbon atom extension. The carbomethoxymethylene group replaces the oxygen of the aldehyde to give a trans- double bond.[1] References1. ^1 2 {{cite journal|last1=Keck|first1=Gary E.|last2=Boden|first2=Eugene P.|last3=Mabury|first3=Scott A.|title=A useful Wittig reagent for the stereoselective synthesis of trans-.alpha.,.beta.-unsaturated thiol esters|journal=The Journal of Organic Chemistry|date=March 1985|volume=50|issue=5|pages=709–710|doi=10.1021/jo00205a036}} 2 : Phosphanes|Esters |
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