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Trimethyl(3-phenylprop-1-ynyl)silane is an organosilicon compound characterized by its molecular formula C12H16Si. It features a silicon atom bonded to three methyl groups and a 3-phenylprop-1-ynyl group, which consists of a phenyl ring attached to a prop-1-ynyl chain. trimethyl(3-phenylprop-1-ynyl)silane is significant in organic synthesis, particularly as a protecting group for alkynes and as a reagent in cross-coupling reactions. Its unique structure allows for selective reactions and can be used to introduce phenyl groups into various organic molecules. Trimethyl(3-phenylprop-1-ynyl)silane is also valued for its stability and the ease with which it can be converted into other functional groups, making it a versatile tool in the field of organic chemistry.

31683-47-3

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31683-47-3 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 31683-47-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,1,6,8 and 3 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 31683-47:
(7*3)+(6*1)+(5*6)+(4*8)+(3*3)+(2*4)+(1*7)=113
113 % 10 = 3
So 31683-47-3 is a valid CAS Registry Number.

31683-47-3Relevant academic research and scientific papers

Pd-catalyzed sp-sp3cross-coupling of benzyl bromides using lithium acetylides

Buter, Jeffrey,Doze, Anna M.,Feringa, Ben L.,Mondal, Anirban,Visser, Paco

, p. 7529 - 7532 (2021/08/05)

Organolithium-based cross-coupling reactions have emerged as an indispensable method to construct C-C bonds. These transformations have proven particularly useful for the direct and fast coupling of various organolithium reagents (sp, sp2, and sp3) with aromatic (pseudo) halides (sp2). Here we present an efficient method for the cross-coupling of benzyl bromides (sp3) with lithium acetylides (sp). The reaction proceeds within 10 min at room temperature and can be performed in the presence of organolithium-sensitive functional groups such as esters, nitriles, amides and boronic esters. The potential application of the methodology is demonstrated in the preparation of key intermediates used in pharmaceuticals, chemical biology and natural products.

Compound of dipyrrolopyridine structure Preparation method and medical application

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Paragraph 0099-0102, (2021/08/25)

The invention discloses a compound with a dipyrrolo-pyridine structure as well as a preparation method and medical application thereof. The compound provided by the invention has obvious inhibitory activity on JAK family proteins, is an effective JAK inhibitor, and has the prospect of being developed into drugs for inhibiting JAK and further treating diseases.

Palladium-Catalyzed Coupling of Terminal Alkynes with Benzyl Ammonium Salts

Xu, Silin,Zhang, Zhenming,Han, Chunyu,Hu, Wenkai,Xiao, Tiwen,Yuan, Yanan,Zhao, Junfeng

, p. 12192 - 12197 (2019/10/11)

A highly efficient palladium-catalyzed Sonogashira coupling of benzylic ammonium salts with terminal alkynes is developed. This strategy provides a facile access to a series of internal alkyne derivatives in moderate to excellent yields via C-N bond cleavage and C(sp3)-C(sp) bond formation. The broad substrate scope and high functional group tolerance make this reaction attractive for organic synthesis.

Pyrazolopyrimidine [3,4-d] compound as well as preparation method and application thereof

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Paragraph 0321; 0323; 0324; 0325, (2019/06/10)

The invention relates to a compound which is a Bruton tyrosine kinase inhibitor. In addition, the invention discloses a pharmaceutical ingredient and a preparation that comprise the compound, and an application of the kinase inhibitor. The compound can be used independently or combined with other compounds for treating kinase mediated or kinase-dependent symptoms.

Propargylsilanes as Reagents for Synergistic Gold(I)-Catalyzed Propargylation of Carbonyl Compounds: Isolation and Characterization of σ-Gold(I) Allenyl Intermediates

Fernández, Sergio,González, Jairo,Santamaría, Javier,Ballesteros, Alfredo

supporting information, p. 10703 - 10707 (2019/06/25)

Reported herein is the isolation and characterization, for the first time, of a σ-gold allenyl complex as an intermediate in gold catalysis. This intermediate was captured during the study of a novel gold(I)-catalyzed propargylation of carbonyl compounds with propargylsilanes. Notably, the gold-catalyzed propargylation reaction, which proceeds with aldehydes and ketones, can be driven to the formation of either homopropargyl silyl ethers or the in situ synthesis of corresponding 2-silyl-4,5-dihydrofurans.

Bifunctional Biphenyl-2-ylphosphine Ligand Enables Tandem Gold-Catalyzed Propargylation of Aldehyde and Unexpected Cycloisomerization

Li, Ting,Zhang, Liming

supporting information, p. 17439 - 17443 (2019/01/04)

Despite extensive studies in gold catalysis, σ-allenylgold species have not been invoked as catalytic intermediates and their reactivities not studied. This work reports for the first time they are generated in situ and undergo nucleophilic addition to activated aldehydes in a bifunctional phosphine ligand-enabled gold catalysis. This development reveals a broad range of opportunities to achieve propargylic C-H functionalization for the first time under catalytic and mild conditions. The homopropargylic alcohols generated undergo ligand-enabled cycloisomerizations involving an unexpected silyl migration.

Regio- and Stereospecific Copper-Catalyzed Substitution Reaction of Propargylic Ammonium Salts with Aryl Grignard Reagents

Guisán-Ceinos, Manuel,Martín-Heras, Victor,Tortosa, Mariola

, p. 8448 - 8451 (2017/07/06)

We have developed a copper-catalyzed substitution reaction of propargylic ammonium salts with aryl Grignard reagents. The reaction is stereospecific and α-regioselective and proceeds with exceptional functional group tolerance. Conveniently, a stable, inexpensive, and commercially available copper salt is used and no added ligand is required.

Regioselective Allylation of Carbon Electrophiles with Alkenyl-silanes under Dual Catalysis by Cationic Platinum(II) Species

Kinoshita, Hidenori,Kizu, Ryosuke,Horikoshi, Masahiro,Inoue, Gen,Fujimoto, Masayuki,Saito, Masanori,Ichikawa, Junji,Hosomi, Akira,Miura, Katsukiyo

supporting information, p. 520 - 534 (2016/02/16)

In the presence of catalytic amounts of platinum(II) chloride and silver(I) hexafluoroantimonate, (Z)-alkenylsilanes reacted with various carbon electrophiles (acetals, aminals, carboxylic anhydrides, alkyl chlorides, etc.) at the γ-position to give allylation products. A plausible mechanism for the platinum-catalyzed allylation involves alkene migration of alkenylsilanes to allylsilanes and subsequent allylation of carbon electrophiles, both of which are catalyzed by a cationic platinum(II) species.

Direct Synthesis of α-Allenols from TMS-Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride

Huang, Xiaojun,Bugarin, Alejandro

supporting information, p. 12696 - 12700 (2016/08/30)

A unique chemoselective synthesis of α-allenic alcohols is presented. Tetrabutylammonium fluoride (TBAF) mediated this transformation under mild reaction conditions. A range of functional groups is well-tolerated in this reaction, while affording adducts

Platinum-catalyzed allylation of carbon electrophiles with alkenylsilanes

Kinoshita, Hidenori,Kizu, Ryosuke,Inoue, Gen,Fujimoto, Masayuki,Saito, Masanori,Ichikawa, Junji,Hosomi, Akira,Miura, Katsukiyo

supporting information, p. 713 - 716 (2015/01/30)

In the presence of catalytic amounts of PtCl2 and AgSbF6, (Z)-alkenylsilanes react with various carbon electrophiles at the γ-position to give allylation products. A plausible mechanism for the Pt-catalyzed allylation involves alkene migration of alkenylsilanes to allylsilanes and subsequent allylation of carbon electrophiles.

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