| 词条 | Otera's catalyst |
| 释义 |
| Verifiedfields = changed | verifiedrevid = 424658175 | ImageFile = Otera's catalyst.svg | ImageSize = 220 | ImageAlt = Skeletal formula of Otera's catalyst | ImageFile1 = Otera's catalyst 3D ball.png | ImageSize1 = 260 | ImageAlt1 = Ball-and-stick model of the Otera's catalyst molecule | IUPACName = | PIN = | OtherNames = Octabutyltetrathiocyanatostannoxane |Section1={{Chembox Identifiers | InChI = 1/8C4H9.2C2HS.2CNS.2O.4Sn/c8*1-3-4-2;2*1-2-3;2*2-1-3;;;;;;/h8*1,3-4H2,2H3;2*1H;;;;;;;;/rC38H74N2O2S4Sn4/c1-9-17-27-47(35-25-43,28-18-10-2)39(37-45)49(31-21-13-5,32-22-14-6)41(47)50(33-23-15-7,34-24-16-8)40(38-46)48(36-26-44,42(49)50,29-19-11-3)30-20-12-4/h35-36H,9-24,27-34H2,1-8H3 | InChIKey = OUBFKIZYHPMZHQ-BIWIHVFOAY | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/8C4H9.2C2HS.2CNS.2O.4Sn/c8*1-3-4-2;2*1-2-3;2*2-1-3;;;;;;/h8*1,3-4H2,2H3;2*1H;;;;;;;; | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = OUBFKIZYHPMZHQ-UHFFFAOYSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 95971-03-2 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID=21106460 | PubChem = | SMILES = CCCC[Sn]1(N(=C=S)[Sn]2(O1[Sn]3(O2[Sn](N3=C=S)(CCCC)(CCCC)N=C=S)(CCCC)CCCC)(CCCC)CCCC)(CCCC)N=C=S }} |Section2={{Chembox Properties | C=36 | H=72 | O=2 | S=4 | Sn=4 | N=4 | MolarMass = | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}Otera's catalyst, named after Japanese chemist Junzo Otera, is an organostannane compound which has been used as a transesterification catalyst. This isothioscyanate compound is a member of a family of organostannanes reported by Wasada and coworkers,[1] and elaborated upon by Otera and coworkers.[2] PreparationThis class of compounds may be prepared generally by the reaction of an organotin halide and oxide:[2] 2 R2SnO + 2 R2SnX2 → (XR2SnOSnR2X)2 In particular, the thiocyanate compound was prepared by the reaction of dibutyltin oxide with dibutyltin diisothiocyanate.[1] Otherwise, this compound is not commercially available. ApplicationsThis thiocyanate compound can be used as a transesterification catalyst.[3] Although it is not well known, it has been used in a number of total syntheses.[4][5] In this application, the reaction occurs via the displacement of the bridging isothiocyanate ligands with the incoming alcohol to form an alcohol-bridged active catalyst. Tin acts as the Lewis acid, and gives the transesterified product.[3][2] References1. ^1 {{cite journal | last1 = Wada | first1 = M | doi = 10.1016/S0022-328X(00)82737-0 | title = Preparation and properties of dialkyltin isothiocyanate derivatives | year = 1965 | pages = 70 | volume = 3 | journal = J. Organomet. Chem.}} 2. ^1 {{cite journal | last1 = Otera | first1 = Junzo. | title = Transesterification | journal = Chem. Rev. | volume = 93 | pages = 1449 | year = 1993 | doi = 10.1021/cr00020a004}} 3. ^1 2 {{cite journal | author=Otera, J| title=Novel template effects of distannoxane catalysts in highly efficient transesterification and esterification | journal=J. Org. Chem. | volume=56 | issue=18 | year=1991 | pages=5307–5311 | doi=10.1021/jo00018a019|display-authors=etal}} 4. ^{{cite journal | author=Trost, BM| title=Synthesis of Amphidinolide P | journal=J. Am. Chem. Soc. | volume=127 | year=2005 | pages=17921–17937|doi=10.1021/ja055967n | pmid=16351124 | issue=50 | pmc=2533515|display-authors=etal}} 5. ^{{cite journal |author1=Trost, BM |author2=Stiles, DT | title=Total Synthesis of Spirotryprostatin B via Diastereoselective Prenylation | journal=Org. Lett. | year=2007|doi=10.1021/ol070971k | volume=9 | pages=2763–6 | pmid=17592853 | issue=15}} 3 : Organotin compounds|Catalysts|Thiocyanates |
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