81353-38-0

Usage

Uses

Used in Organic Chemistry Research:
1-Tributylstannyl-2-Trimethylsilylacetylene is used as a reagent for synthesis in organic chemistry research. Its unique properties allow researchers to develop new materials and facilitate complex chemical reactions.
Used in Chemical Manufacturing:
1-Tributylstannyl-2-Trimethylsilylacetylene is used as a reagent in the manufacturing of various chemical products. Its complex structure and properties enable the production of new compounds and materials with potential applications in different industries.

InChI:InChI=1/C5H9Si.3C4H9.Sn/c1-5-6(2,3)4;3*1-3-4-2;/h2-4H3;3*1,3-4H2,2H3;/rC17H36SiSn/c1-7-10-14-19(15-11-8-2,16-12-9-3)17-13-18(4,5)6/h7-12,14-16H2,1-6H3

Upstream product

• 1461-22-9 tributyltin chloride 
• 1066-54-2 trimethylsilylacetylene 
• 1067-52-3 tributyltin methoxide 
• 688-73-3 tri-n-butyl-tin hydride 
• 101069-08-3 (diisopropylamino)tributylstannane 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 

Downstream Products

• 124828-80-4 N-Phenyl-3-trimethylsilanyl-propynimidothioic acid phenyl ester 
• 97367-34-5 1-(trimethylsilyl)-8-nonen-1-yn-3-one 
• 122016-24-4 (N-phenyl)bis(trimethylsilylethynyl)imine 
• 110598-59-9 N-acetyl-2-<(trimethylsilyl)ethynyl>aniline 
• 122016-27-7 Cyclohexyl-(3-trimethylsilanyl-1-trimethylsilanylethynyl-prop-2-ynylidene)-amine 
• 127357-61-3 diphenylmethyl 2-amino-N-acetyl-4-(trimethylsilyl)-3-butynoate 
• 130837-49-9 3-Methyl-4-trimethylsilanylethynyl-cyclobut-3-ene-1,2-dione 
• 114094-75-6 3-(1-methylethoxy)-4-<(trimethylsilyl)ethynyl>cyclobut-3-ene-1,2-dione 
• 118908-01-3 5-<2-(trimethylsilyl)-1-ethyn-1-yl>-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 84213-96-7 trans-N-(1-naphthylmethyl)-N-methyl-5-trimethylsilyl-pent-2-en-4-ynyl-1-amine 
• 123028-09-1 N-acetyl-2-<(trimethylsilyl)ethynyl>-5-carbomethoxyaniline 
• 139337-48-7 [3-Indan-(1Z)-ylidene-prop-1-ynyl]-trimethyl-silane 
• 139337-52-3 {3-[3,4-Dihydro-2H-naphthalen-(1Z)-ylidene]-prop-1-ynyl}-trimethyl-silane 
• 144216-54-6 4-methoxy-5-nitro-6-(trimethylsilylethynyl)pyrimidine 

Relevant academic research and scientific papers

Palladium-Catalyzed Diastereoselective Synthesis of (Z)-Conjugated Enynyl Homoallylic Alcohols

The diastereoselective synthesis of anti-homoallylic alcohols bearing conjugated (Z)-enynes through a palladium-catalyzed three-component reaction is described. This reaction features a broad substrate scope, good functional group compatibility, and high levels of (Z)-alkene stereocontrol. In this reaction, Pd(0) functions as a catalyst in two fundamental steps of the tandem sequence: 1) the generation of a borylated π-allylpalladium species from bifunctional conjunctive reagents, inducing umpolung allylation of aldehydes, and 2) C(sp2)?C(sp) cross-coupling. Further transformations of the obtained products highlight their synthetic utility. (Figure presented.).

Catalytic Dehydrogenative Stannylation of C(sp)-H Bonds Involving Cooperative Sn-H Bond Activation of Hydrostannanes

The catalytic generation of a stannylium-ion-like tin electrophile by heterolytic cleavage of the Sn-H bond in hydrostannanes at the Ru-S bond of Ohki-Tatsumi complexes is reported. Reacting these activated hydrostannanes with terminal acetylenes does not lead to hydrostannylation of the C-C triple bond but to dehydrogenative stannylation of the alkyne terminus. The scope of this rare direct C(sp)-H bond stannylation with hydrostannanes is broad, and a mechanism involving a β-tin-stabilized vinyl cation likely having a bridged structure is presented.

PHENACENE COMPOUNDS FOR ORGANIC ELECTRONICS

Phenacene compounds of formula (I) wherein R1 and R2 are independently of each other a linear or branched C1-20 alkyl group.

GaBr3-catalyzed Coupling between α-Iodo Esters with Alkynylstannanes under UV Irradiation

A coupling between various alkynylstannanes with α-iodo esters was catalyzed by GaBr3 under UV irradiation conditions, for which a catalytic amount of GaBr3 was essential, and a radical coupling with the generated alkynylgallium species was involved. The desired α-alkynyl esters were selectively obtained even in the presence of an aryl-I bond, which is a reactive site in a conventional palladium-catalyzed system.

Phosphine-Free Stille-Migita Chemistry for the Mild and Orthogonal Modification of DNA and RNA

An optimized catalyst system of [Pd2(dba)3] and AsPh3 efficiently catalyzes the Stille reaction between a diverse set of functionalized stannanes and halogenated mono-, di- and oligonucleotides. The methodology allows for the facile conjugation of short and long nucleic acid molecules with moieties that are not compatible with conventional chemical or enzymatic synthesis, among them acid-, base-, or fluoride-labile protecting groups, fluorogenic and synthetically challenging moieties with good to near-quantitative yields. Notably, even azides can be directly introduced into oligonucleotides and (deoxy)nucleoside triphosphates, thereby giving direct access to "clickable" nucleic acids.

Sequential Norrish type II photoelimination and intramolecular aldol cyclization of α-diketones: Synthesis of polyhydroxylated cyclopentitols by ring contraction of hexopyranose carbohydrate derivatives

The excitation of the innermost carbonyl of nono-2,3-diulose derivatives by irradiation with visible-light initiates a sequential Norrish type II photoelimination and aldol cyclization process that finally gives polyfunctionalized cyclopentitols. The rearrangement has been confirmed by the isolation of stable acyclic photoenol intermediates that can be independently cyclized by a thermal 5-(enolexo)-exo-trig uncatalyzed aldol reaction with high diastereoselectivity. In this last step, the large deuterium kinetic isotope effect found for the 1,5-hydrogen atom transfer seems to indicate that the aldol reaction runs through a concerted pericyclic mechanism. Owing to the ready availability of pyranose sugars of various configurations, this protocol has been used to study the influence of pyranose ring-substituents on the diastereoselectivity of the aldol cyclization reaction. In contrast with other pyranose ring contraction methodologies no transition-metal reagents are needed and the sequential rearrangement occurs simply by using visible light and moderate heating (0 to 60 °C). Copyright

PHENACENE COMPOUNDS FOR ORGANIC ELECTRONICS

Phenacene compounds of formula (I) are disclosed. All the variables in the formula are the same as defined in the description. A thin film semiconductor comprising the above compounds, and a field effect transistor device, a photovoltaic device, an organic light emitting diode device and a unipolar or complementary circuit device comprising the thin film are also disclosed.

Direct synthesis of alkynylstannanes: ZnBr2 catalyst for the reaction of tributyltin methoxide and terminal alkynes

Metal hopping: Various alkynylstannanes were synthesized by the direct reaction of Bu3SnOMe with terminal alkynes at room temperature in the presence of a ZnBr2 catalyst. Rather than acting as a Lewis acid, ZnBr2 was transmetalated with Bu3SnOMe to give Zn(OMe)2, which is key to the catalytic reaction. Copyright

The β-effect with vinyl cations: Kinetic study of the protiodemetalation of silyl-, germyl-, and stannylalkynes

The relative magnitude of the hyperconjugative stabilization of vinyl cations by adjacent C-M bonds (M = Si, Ge, Sn; the β-effect) has been examined by measuring the rate constants for the protonation and subsequent protiodemetalation of group 14 metalated (trimethylsilyl)-acetylenes (R3MC≡CSiMe3). The relative β-effect arising from the second-order rate constants Sn ? Ge > Si (maximum kM/kSi = 108, 5 × 102, 1, respectively) follows the same order as that reported for simple carbenium ions. The product ratio from the protonation of Ph3GeC≡CSiMe3 was found to be particularly sensitive to acid concentration and strength, leading to loss of Ph3Ge preferentially with weaker acids. With tin groups, the rate of destannylation decreased with increasing steric bulk, unlike the corresponding situation with silyl groups. The origins of both these observations may be attributed to nucleophilic interaction at the metal center during protonation.

Imidazole derivatives, process for production thereof, and use thereof

Disclosed are imidazole derivatives represented by formula [I]: STR1 wherein R is a hydrogen atom or STR2 wherein R2 is a hydrogen atom or a hydroxy protecting group, R2 protecting either a single hydroxy or two hydroxies together when R2 is a hydroxy protecting group, and R3 is a hydrogen atom or OR2 ; A is CONH2 or CN; and R1 is a hydrogen atom, lower alkyl, hydroxy lower alkyl, or phenyl. Also disclosed are six processes for producing these novel compounds among which a typical process comprises reacting a starting imidazole compound having a halogen at the 5-position thereof with an acetylene derivative to alkynylate the 5-position. Furthermore, the compounds having remarkable antitumor activities and therefore can provide novel antitumor agents.