| 词条 | Thiocarbonyldiimidazole |
| 释义 |
| ImageFile = 1,1'-thiocarbonyldiimidazole.png | ImageSize = | ImageAlt =1,1'-thiocarbonyldiimidazole | IUPACName = Di(imidazol-1-yl)methanethione | OtherNames = TCDI | Section1 = {{Chembox Identifiers | CASNo = 6160-65-2 | PubChem = 80264 | SMILES = C1=CN(C=N1)C(=S)N2C=CN=C2 | InChI=1S/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H | InChIKey=RAFNCPHFRHZCPS-UHFFFAOYSA-N | EC_number = 228-183-4 | Section2 = {{Chembox Properties | C=7 | H=6 | N=4 |S=1 | Appearance = | Density = | MeltingPtC = 101 to 103 | BoilingPt = | Solubility = | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} 1,1'-Thiocarbonyldiimidazole (TCDI) is a thiourea containing two imidazole rings.[1] It is the sulfur analog of the peptide coupling reagent carbonyldiimidazole (CDI). SynthesisTCDI is commercially available but can also be prepared via the reaction of thiophosgene with two equivalents of imidazole.[1] ReactionsThe imidazole groups on TCDI can be easily displaced, allowing it to act as a safer alternative to thiophosgene. This behaviour has been used in the Corey–Winter olefin synthesis.[2] It may also replace carbonothioyl species (RC(S)Cl) in the Barton–McCombie deoxygenation. Other uses include the synthesis of thioamides and thiocarbamates. Like the analogous CDI, it may be used for peptide coupling.[3] References1. ^1 {{cite journal |last1=Adrian |first1=L. Schwan |last2=Jeffrey |first2=H. Byers |title=1,1′‐Thiocarbonyldiimidazole |journal=Encyclopedia of Reagents for Organic Synthesis |date=15 March 2007 |doi=10.1002/9780470842898.rt094.pub2}} 2. ^{{cite journal |last1=Corey |first1=E. J. |last2=Winter |first2=Roland A. E. |title=A New, Stereospecific Olefin Synthesis from 1,2-Diols |journal=Journal of the American Chemical Society |date=September 1963 |volume=85 |issue=17 |pages=2677–2678 |doi=10.1021/ja00900a043}} 3. ^{{cite journal |last1=Esser |first1=Franz |last2=Roos |first2=Otto |title=N-Terminal Cyclization of Peptides withN,N′-Carbonyldiimidazole orN,N′-Thiocarbonyldiimidazole |journal=Angewandte Chemie International Edition in English |date=June 1978 |volume=17 |issue=6 |pages=467–468 |doi=10.1002/anie.197804671}} 3 : Thioureas|Imidazoles|Peptide coupling reagents |
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