229027-92-3

Upstream product

• 5159-41-1 2-iodobenzyl alcohol 
• 1066-54-2 trimethylsilylacetylene 
• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 18982-54-2 o-bromobenzyl alcohol 
• 56053-89-5 5-trimethylsilanyl-penta-2,4-diyn-1-ol 
• 74-86-2 acetylene 
• 77123-57-0 4-[(trimethylsilyl)ethynyl]bezaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 107793-07-7 methyl 2-(2-trimethylsilyl-1-ethynyl)benzoate 

Downstream Products

• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 220798-69-6 (2-ethynyl-phenyl)-methaneselenol 
• 1093658-73-1 trimethyl(2-((trimethylsilyl)ethynyl)benzyloxy)silane 
• 84666-75-1 1,3-dihydro-(1-methylene)isobenzofuran 
• 1418758-72-1 (1'S,4R)-N-(3,5-dimethoxyphenyl)-3'H-spiro[chroman-2,1'-isobenzofuran]-4-amine 
• 1418758-68-5 (1'S,4R)-N-phenyl-3'H-spiro[chroman-2,1'-isobenzofuran]-4-amine 
• 1418758-69-6 (1'S,4R)-N-(4-methoxyphenyl)-3'H-spiro[chroman-2,1'-isobenzofuran]-4-amine 
• 1418758-70-9 (1'S,4R)-N-p-tolyl-3'H-spiro[chroman-2,1'-isobenzofuran]-4-amine 

Relevant academic research and scientific papers

Structural Basis for Genetic-Code Expansion with Bulky Lysine Derivatives by an Engineered Pyrrolysyl-tRNA Synthetase

Yanagisawa et al. analyzed the Y306A/Y384F mutant of Methanosarcina mazei pyrrolysyl-tRNA synthetase (PylRS) with 17 non-natural, bulky oxycarbonyllysine derivatives for tRNAPyl aminoacylation and site-specific incorporation into proteins. Fourteen crystal structures of the amino acid-bound PylRS mutant revealed the structural bases of the binding. This information facilitates the structure-based design of novel amino acids. Pyrrolysyl-tRNA synthetase (PylRS) and tRNAPyl have been extensively used for genetic-code expansion. A Methanosarcina mazei PylRS mutant bearing the Y306A and Y384F mutations (PylRS(Y306A/Y384F)) encodes various bulky non-natural lysine derivatives by UAG. In this study, we examined how PylRS(Y306A/Y384F) recognizes many amino acids. Among 17 non-natural lysine derivatives, N?-(benzyloxycarbonyl)lysine (ZLys) and 10 ortho/meta/para-substituted ZLys derivatives were efficiently ligated to tRNAPyl and were incorporated into proteins by PylRS(Y306A/Y384F). We determined crystal structures of 14 non-natural lysine derivatives bound to the PylRS(Y306A/Y384F) catalytic fragment. The meta- and para-substituted ZLys derivatives are snugly accommodated in the productive mode. In contrast, ZLys and the unsubstituted or ortho-substituted ZLys derivatives exhibited an alternative binding mode in addition to the productive mode. PylRS(Y306A/Y384F) displayed a high aminoacylation rate for ZLys, indicating that the double-binding mode minimally affects aminoacylation. These precise substrate recognition mechanisms by PylRS(Y306A/Y384F) may facilitate the structure-based design of novel non-natural amino acids.

Synthesis of Functionalised 3-Isochromanones by Silylcarbocyclisation/Desilylation Reactions

A new protocol for the synthesis of 3-isochromanone derivatives based on rhodium-promoted silylcarbocyclisation reactions of ethynylbenzyl alcohol with different arylsilanes is described. The structure of the isochromanone depends upon the reaction condit

Synthesis and Properties of Functional Twisted Tolanes

The synthesis and optical properties of several novel fluorescent and/or phosphorescent bridged tolanes (tolanophanes) are reported and their optical and structural properties are investigated. Specifically, diiodinated and bisalkynylated tolanophanes were obtained, and characterized by spectroscopy and computational methods. They represent attractive building blocks for novel polymers and emissive solid-state materials.

Intramolecular C-H activation through gold(I)-catalyzed reaction of iodoalkynes

The cycloisomerization reaction of 1-(iodoethynyl)-2-(1-methoxyalkyl)arenes and related 2-alkyl-substituted derivatives gives the corresponding 3-iodo-1-substituted-1H-indene under the catalytic influence of IPrAuNTf2 [IPr = 1,3-bis(2,6-diisopropyl)phenylimidazol-2-ylidene; NTf2 = bis(trifluoromethanesulfonyl)imidate]. The reaction takes place in 1,2-dichloroethane at 80°C, and the addition of ttbp (2,4,6-tritert-butylpyrimidine) is beneficial to accomplish this new transformation in high yield. The overall reaction implies initial assembly of an intermediate gold vinylidene upon alkyne activation by gold(I) and a 1,2-iodine-shift. Deuterium labeling and crossover experiments, the magnitude of the recorded kinetic primary isotopic effect, and the results obtained from the reaction of selected stereochemical probes strongly provide support for concerted insertion of the benzylic C-H bond into gold vinylidene as the step responsible for the formation of the new carbon-carbon bond.

Formation and in situ reactions of hypervalent iodonium alkynyl triflates to form cyanocarbenes

The conversion of readily available silylalkynes, iodobenzene diacetate, and azide anions was utilized to form and react cyanocarbenes. A copper(ii)-catalyzed reaction was found to react in a different manner. Both of these methods benefit from the formation and in situ reaction of hypervalent iodonium alkynyl triflates in O-H insertion reactions. This journal is

Concise synthesis of the tricyclic skeleton of crotobarin and crotogoudin via a gold-catalyzed cycloisomerization reaction

A concise synthesis of the tricyclic skeleton of crotobarin and crotogoudin via a gold-catalyzed 1,6-enyne cycloisomerization reaction is reported.

Direct access to enantioenriched spiroacetals through asymmetric relay catalytic three-component reaction

The gold(I)/chiral Br?nsted acid relay catalysis enabled a highly stereoselective three-component reaction of salicylaldehydes, anilines, and alkynols to give aromatic spiroacetals in high yields and stereoselectivities.

A simple and mild synthesis of 1H-isochromenes and (Z)-1-alkylidene-1,3- dihydroisobenzofurans by the iodocyclization of 2-(1-alkynyl)benzylic alcohols

(Chemical Equation Presented) A variety of iodo-substituted isochromenes, dihydroisobenzofurans, and pyranopyridines are readily prepared in good to excellent yields under mild conditions by the iodocyclization of readily available 2-(1-alkynyl)benzylic a

Gold- or platinum-catalyzed synthesis of sulfur heterocycles: access to sulfur ylides without using sacrificial functionality

It's no sacrifice: Alkynes have been used as direct precursors to sulfur ylides under gold or platinum π-acid catalysis in an atom-economic manner. An intramolecular redox reaction between an alkyne group with a tethered sulfoxide unit gen-erates a sulfur ylide, which undergoes 2,3sigmatropic rearrangement. Acyclic substrates are cycloisomerized to afford functionalized dihydrothiophenones (see scheme) and dihydrothiopyranones.

An unusual access to medium sized cycloalkynes by a new goId(I)-catalysed cycloisomerisation of diynes

A study was conducted to demonstrate efficient cycloisomerization of a series of 1,9- and 1,10-diynes into medium sized cycloalkynes by a gold-catalyzed alkyne-alkyne coupling. The reaction was performed using 4 mol% of gold complex in CD2Cl2 at room temperature and was monitored by using 1H NMR spectroscopy. The reaction of analogous diyne substrate was more rapid and a complete conversion was observed after 40 hours at room temperature. The cycloalkyne was isolated as a solid in 95% yield from which single crystals suitable for X-ray crystal structure determination was obtained. A rapid screening of catalysts and experimental conditions was undertaken to optimize the formation of cycloalkyne. A mechanistic proposal was also introduced for the cycloisomerization of diynes into cycloalkynes on the basis of the experimental observations.