| 词条 | 9-Borabicyclo(3.3.1)nonane |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | Name = 9-Borabicyclo[3.3.1]nonane | verifiedrevid = 477227844 | ImageFile1 = 9-BBN dimer structure.svg | ImageSize1 = 80px | ImageFile2 = 9-BBN-dimer-xtal-3D-sticks-skeletal.png | ImageSize2 = | ImageFile3 = BBN_Crystals.jpg | IUPACName = 9-Borabicyclo[3.3.1]nonane | OtherNames = Borabicyclononane Banana borane |Section1={{Chembox Identifiers | Abbreviations = 9-BBN | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2 | CASNo_Ref = {{cascite|changed|??}} | CASNo = 280-64-8 | EINECS = 206-000-9 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 71299 | PubChem = 6327450 | SMILES = B1([H]3)(C2CCCC1CCC2)[H]B34C2CCCC4CCC2 | InChI = 1/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2 | InChIKey = FEJUGLKDZJDVFY-UHFFFAOYAE | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = FEJUGLKDZJDVFY-UHFFFAOYSA-N | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = |Section2={{Chembox Properties | C=16 | H=30 | B=2 | Appearance = | Density = 0.894 g/cm3 | MeltingPtC = 153 to 155 | MeltingPt_notes = | BoilingPt = | BoilingPt_notes = | Solubility = Reacts | SolubleOther = | Solvent = | pKa = | pKb = }} |Section7={{Chembox Hazards | EUClass = | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | RPhrases = {{R11}} {{R14/15}} {{R36/37/38}} | SPhrases = {{S7/9}} {{S16}} {{S33}} {{S7/8}} {{S26}} {{S37/39}} | RSPhrases = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = }} 9-Borabicyclo[3.3.1]nonane or 9-BBN is an organoborane compound. This colourless solid is used in organic chemistry as a hydroboration reagent. The compound exists as a hydride-bridged dimer, which easily cleaves in the presence of reducible substrates.[1] 9-BBN is also known by its nickname 'banana borane'.[2] This is because rather than drawing out the full structure, chemists often simply draw a banana shape with the bridging boron.[3]{{Better source|date=March 2016}} Preparation9-BBN is prepared by the reaction of 1,5-cyclooctadiene and borane usually in ethereal solvents, for example:[4][5] The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.[6][7][8] Its highly regioselective addition on alkenes allows the preparation of terminal alcohols by subsequent oxidative cleavage with H2O2 in aqueous KOH. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane. References1. ^{{cite book|last=Brown|first=H. C.|title=Organic Syntheses via Boranes|publisher=John Wiley & Sons|location=New York|date=1975|ISBN=0-471-11280-1}} 2. ^{{cite web|last1=Stix|first1=Gary|title=The Straight Dope: A Q&A with the Prof behind the Good Science in Breaking Bad|url=https://blogs.scientificamerican.com/talking-back/the-straight-dope-a-qa-with-the-prof-behind-the-good-science-in-breaking-bad/|website=Scientific American Blog Network|publisher=Nature America, Inc.|accessdate=18 June 2017|language=en}} 3. ^{{cite web|url=http://www.chm.bris.ac.uk/sillymolecules/sillymols3.htm |title=Molecules with Silly or Unusual Names - page 3 |website=Chm.bris.ac.uk |date=2014-05-07 |accessdate=2016-06-01}} 4. ^{{cite journal | title = Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo[3.3.1]nonane (9-BBN) dimer | first1= John A.|last1= Soderquist | first2 = Herbert C.|last2= Brown | author2-link = Herbert C. Brown | journal = J. Org. Chem. | year = 1981 | volume = 46 | issue = 22 | pages = 4599–4600 | doi = 10.1021/jo00335a067}} 5. ^{{OrgSynth | collvol = 9 | collvolpages = 95 | year= 1998 | title = 9-Borabicyclo[3.3.1]nonane Dimer | first1= John A. |last1=Soderquist | last2 = Alvin |first2=Negron | prep = cv9p0095}} 6. ^{{OrgSynth | first1= Tatsuo|last1= Ishiyama | first2 = Norio |last2=Miyaura | first3 = Akira |last3=Suzuki | title = Palladium(0)-catalyzed reaction of 9-alkyl-9-borabicyclo[3.3.1]nonane with 1-bromo-1-phenylthioethene: 4-(3-cyclohexenyl)-2-phenylthio-1-butene | collvol = 9 | collvolpages = 107 | prep = cv9p0107}} 7. ^{{cite journal|first1=A. |last1=Balog|first2= D. |last2=Meng|first3= T.|last3= Kamenecka|first4= P.|last4= Bertinato|first5= D.-S.|last5= Su|first6= E. J.|last6= Sorensen |first7=S. J. |last7=Danishefsky |title=Total Synthesis of (−)-Epothilone A|journal= Angew. Chem. Int. Ed. Engl.|date=1996|volume= 35|page= 2801 |DOI=10.1002/anie.199628011}} 8. ^{{cite journal|first1= J.|last1= Liu|first2= S. D. |last2=Lotesta |first3= E. J. |last3=Sorensen |title=A concise synthesis of the molecular framework of pleuromutilin |journal=Chem. Commun. |date=2011|volume= 47|page= 1500 |DOI=10.1039/C0CC04077K |pmid=21079876 |pmc=3156455}} See also
2 : Organoboranes|Reagents for organic chemistry |
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