| 词条 | Propynyllithium |
| 释义 |
| ImageFile = Propynyllithium Structural Formula V1.svg | ImageSize = 200px | ImageAlt = | IUPACName = 1-Lithium-1-propyne | OtherNames = 1-Propyn-1-yllithium | Section1 = {{Chembox Identifiers | CASNo = 4529-04-8 | PubChem = 78287 | ChemSpiderID = 10488464 | EINECS = 224-862-4 | SMILES = [Li+].CC#[C-] | StdInChI= 1S/C3H3.Li/c1-3-2;/h1H3;/q-1;+1 | StdInChIKey= ATKCLEUSJFRRKA-UHFFFAOYSA-N | Section2 = {{Chembox Properties | C=3|H=3|Li=1 | Appearance = Whitish powder | Density = | Solubility = Decomposition | MeltingPt = | BoilingPt = | VaporPressure = | Section3 = {{Chembox Hazards | MainHazards = | GHSPictograms = {{GHS02}} {{GHS05}} | FlashPt = | AutoignitionPt = }}Propynyllithium is an organolithium compound with the chemical formula {{chem|Li|C|2|C|H|3}}. It is a white solid that quickly decomposes upon contact with air or water. It is soluble in 1,2-dimethoxyethane, and tetrahydrofuran. To preclude degradation by oxygen and water, propynyllithium and its solutions are handled under inert gas (Ar or {{chem|N|2}}).[1] SynthesisVarious preparations of propynyllithium are known, but the most expeditious route starts with 1-bromopropene:[2][3] CH3CH=CHBr + 2 BuLi → CH3C2Li + 2 BuH + LiBr Historic routesIt can be prepared by passing propyne gas through a solution of n-butyllithium[4] or by direct metallization of propyne with lithium in liquid ammonia or other solvent. Propyne, however, is an expensive gas, and, therefore, it is sometimes replaced by less expensive gas mixtures used for welding and containing a small percentage of propyne. ApplicationsPropynyllithium is used in the organic synthesis as a reactant.[2][5] It is a nucleophile that adds to aldehydes to give secondary alcohols, with ketones to give tertiary alcohols, and with acid chlorides to give ketones containing the propynyl group. These reactions are used in the synthesis of complex natural and synthetic substances such as the drug mifepristone.[6] References1. ^{{cite book|last1=Greeves|first1=Nicholas|title=Encyclopedia of Reagents for Organic Synthesis|publisher=onlinelibrary.wiley.com|doi=10.1002/047084289X.rp277|date=15 April 2001|isbn=978-0471936237|chapter=Propynyllithium}} 2. ^1 {{cite journal|title=Synthesis of 1-Iodopropyne|authors=Samuel G. Bartko, James Deng, and Rick L. Danheiser|journal=Org. Synth.|year=2016|volume=93|page=245|doi=10.15227/orgsyn.093.0245}} 3. ^{{cite journal|last1=Toussaint|first1=Dominique|last2=Suffert|first2=Jean|title=Generation of 1-Propynyllithium From (Z/E)-1-Bromo-1-propene: 6-Phenylhex-2-yn-5-en-4-ol|journal=J. Org. Chem.|date=1999|volume=vol. 60|page=3550–3553}} 4. ^{{cite web|title=Acetylenic lead compounds and gasoline compositions thereof US 3185553 A|url=http://www.google.nl/patents/US3185553|accessdate=17 May 2017}} 5. ^{{cite web|title=Acetylenic lead compounds and gasoline compositions thereof US 3185553 A|url=http://www.google.nl/patents/US3185553|accessdate=17 May 2017}} 6. ^{{cite journal|last1=Hazra|first1=B.G.|last2=Pore|first2=V.S.|title=Mifepristone (RU-486), the recently developed antiprogesterone drug and its analogues|journal=Journal of the Indian Institute of Science|date=2001|volume=vol. 81|page=287–298}} External links
2 : Organolithium compounds|Alkynes |
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