| 词条 | Triazabicyclodecene |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470613105 | Reference =[1] | ImageFileL1 =Triazabicyclodecene (molecular structure).png | ImageFileR1 =TBD 2.png | IUPACName =1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine | OtherNames = 1,5,7-Triazabicyclo[4.4.0]dec-5-ene TBD Hexahydropyrimidopyrimidine hpp |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 72164 | InChI = 1/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9) | InChIKey = FVKFHMNJTHKMRX-UHFFFAOYAP | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = FVKFHMNJTHKMRX-UHFFFAOYSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo =5807-14-7 | PubChem =79873 | SMILES = N\\2=C1/NCCCN1CCC/2 }} |Section2={{Chembox Properties | Formula =C7H13N3 | MolarMass =139.20 g/mol | Appearance = | Density = | MeltingPtC = 125 to 130 | MeltingPt_notes = | BoilingPt = | Solubility = | pKa = 15.2 ± 1.0[2] (pKa of conjugate acid in water); 26.03[3] (pKa of conjugate acid in acetonitrile) |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | SPhrases = {{S26}} {{S36/37/39}} {{S45}} | RPhrases = {{R34}} }}Triazabicyclodecene (1,5,7-Triazabicyclo[4.4.0]dec-5-ene or TBD) is a commercially available bicyclic strong guanidine base (pKa = 25.98 in CH3CN and pKa = 21.00 in THF). TBD is an organic soluble base which has been used effectively for a variety of base-mediated organic transformations such as:[4]
It is also known in deprotonated form (at the 7-position), often as a ligand, for instance in Ditungsten tetra(hpp) References1. ^1,5,7-Triazabicyclo[4.4.0]dec-5-ene] at Sigma-Aldrich 2. ^{{cite journal | last1 = Kaupmees | first1 = K. | last2 = Trummal | first2 = A. | last3 = Leito | first3 = I. | title = Basicities of Strong Bases in Water: A Computational Study | journal = Croat. Chem. Acta | year = 2014 | volume = 87 | pages = 385–395 | doi = 10.5562/cca2472 }} 3. ^{{cite journal | last1 = Kaljurand | first1 = I. | last2 = Kütt | first2 = A. | last3 = Sooväli | first3 = L. | last4 = Rodima | first4 = T. | last5 = Mäemets | first5 = V. | last6 = Leito | first6 = I. | last7 = Koppel | first7 = I. A. | title = Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales | journal = J. Org. Chem. | year = 2005 | volume = 70 | pages = 1019–1028 | doi = 10.1021/jo048252w | pmid=15675863}} 4. ^{{cite encyclopedia|first1=Adam|last1=Huczynski|first2=Bogumil|last2=Brzezinski|title=1,5,7-Triazabicyclo[4.4.0]dec-5-ene|encyclopedia=e-EROS Encyclopedia of Reagents for Organic Synthesis|publisher=John Wiley & Sons|date=2008|doi=10.1002/047084289X.rn00786}} 5. ^{{cite journal|first1=Cyrille|last1=Sabot|first2=Kanduluru Ananda|last2=Kumar|first3=Stéphane|last3=Meunier|first4=Charles|last4=Mioskowski|title=A convenient aminolysis of esters catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditions|journal=Tetrahedron Lett.|date=2007|pages=3863–3866|doi=10.1016/j.tetlet.2007.03.146}} 6. ^{{cite journal|title=Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters|first1=Russell C.|last1=Pratt|first2=Bas G. G.|last2=Lohmeijer|first3=David A.|last3=Long|first4=Robert M.|last4=Waymouth|first5=James L.|last5=Hedrick|journal=J. Am. Chem. Soc.|date=2006|volume=128|issue=14|pages=4556–4557|doi=10.1021/ja060662+}} 7. ^Reaction specs: initiator 4-pyrenebutanol (pyrene enables end-group determination by UV–vis) and monomer caprolactone added in ratio 1:100, targeted degree of polymerization = 100, with TBD cat. 0.5% in benzene; 72% conversion in 8 hours; polydispersity index 1.16 8. ^{{cite journal|first1=A.|last1=Huczyński|first2=I.|last2=Binkowska|first3=A.|last3=Jarczewski|first4=B.|last4=Brzezinski|title=Spectroscopic studies of the 1:1 complexes of 4-nitrophenyl(bis(ethylsulfonyl))methane and phenyl(bis(ethylsulfonyl))methane with 7-methyl-1,5,7-triazabicyclo(4.4.0)dec-5-ene and 1,5,7-triazabicyclo(4.4.0)dec-5-ene|journal=J. Mol. Struc.|volume=841|issue=1–3|date=2007|pages=133–136|doi=10.1016/j.molstruc.2007.01.005}} 6 : Catalysts|Guanidines|Pyrimidopyrimidines|Amines|Heterocyclic compounds|Reagents for organic chemistry |
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