405064-44-0

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 405064-47-3 1-(3-methoxyphenyl)-3-(trimethylsilyl)prop-2-yn-1-one 
• 405064-50-8 [4,4-dibromo-3-(3-methoxyphenyl)-buten-1-ynyl]trimethylsilane 
• 1005002-75-4 1-(3-methoxyphenyl)-2-oxopropyl acetate 
• 179248-84-1 1-(3-methoxyphenyl)prop-2-yn-1-ol 
• 179249-08-2 1-(3-methoxyphenyl)prop-2-yn-1-yl acetate 
• 1297409-45-0 1-(3-methoxyphenyl)-2-(5-(3-methoxyphenyl)furan-2-yl)ethanone 
• 1297409-06-3 1,6-bis(3-methoxyphenyl)hexa-2,4-diyne-1,6-diol 
• 1352742-25-6 (R)-1-(3-methoxyphenyl)-3-(trimethylsilyl)prop-2-ynyl acetate 
• 252893-52-0 1-(3-methoxyphenyl)prop-2-yn-1-one 

Relevant academic research and scientific papers

Synthesis and evaluation of aminopyridine derivatives as potential BACE1 inhibitors

To identify a new non-peptidyl BACE1 inhibitor, we focused on the aminopyridine structure, which binds to the active sites of BACE1. Synthesis of aminopyridine derivatives and evaluation of inhibitory activity against rBACE1 are described. The 2-aminopyri

Direct spirocyclization from keto-sulfonamides: An approach to azaspiro compounds

Spontaneous spirocyclization of keto-sulfonamides via ynamides through a one-pot process is presented. Push-pull ynamides were obtained through Michael addition/elimination without Cu. The obtained azaspiro compounds are building blocks for indole alkaloids. Theoretical studies provide insights into the mechanism of the formal Conia-ene reaction.

Silver(I)-catalyzed reaction between pyrazole and propargyl acetates: Stereoselective synthesis of the scorpionate ligands (E)-allyl-gem-dipyrazoles (ADPs)

The reaction between readily accessible pyrazole and propargyl acetates in the presence of Ag(I) catalyst yielded a new class of (E)-allyl-gem-dipyrazole scorpionate ligands: 1-aryl-2-N-pyrazolyl allyl acetates and 1,3-dipyrazolyl-3-arylpropene. The reaction showed broad substrate scope, and various functional and protecting groups were tolerated under the reaction conditions. The palladium(II) scorpionate complex could thus be easily prepared and successfully employed in Suzuki-Miyaura cross-couplings in water.

Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: Access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol B

A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph 3PAuCl and 1% AgSbF6 in dioxane-H2O efficiently hydrolyzes the terminal alkynes of the propargyl acetate in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group as demonstrated through 18O-labeling study. Compatibility of functional moieties and tolerance to various acid-labile protecting groups are observed. The catalytic condition is also suitable to perform hydration of TMS-substituted propargyl acetates, even though it requires prolonged reaction time for completion. Stereointegrity of the propargylic acetate is preserved during the hydration. The robustness of the system is successfully demonstrated through gram scale preparation of the product in nearly quantitative yield. The common α-acyloxy methyl ketone is transformed to 1,2-diol and 1,2-amino alcohol derivatives. Synthesis of actinopolymorphol B is achieved for the first time involving hydration of the propargyl acetate as the key step.

Base-catalyzed cascade 1,3-H shift/cyclization reaction to construct polyaromatic furans

A convenient new method was developed to prepare unfused polyaromatic furan derivatives from diynyl-1,6-diols through a novel base-catalyzed cascade 1,3-H shift/cyclization process. Deuterium experiments were performed to determine that the 1,3-H shift was the rate-determining step. Copyright

Highly enantioselective addition of trimethylsilylacetylene to aldehydes catalyzed by a zinc-amino-alcohol complex

A fine addition! A highly enantioselective and efficient procedure for the amino-alcohol-zinc-catalyzed addition of trimethylsilylacetylene to aromatic, α,β-unsaturated, and aliphatic aldehydes has been developed (see scheme; R=aryl, alkynyl, or alkyl; TMS=trimethylsilyl; TBDMS=tert- butyldimethylsilyl). The present protocol was successfully applied in the concise synthesis of the natural products marine alkynol and falcarindiol. Copyright

Bisoxazolidine-catalyzed enantioselective alkynylation of aldehydes

A C2-symmetric bisoxazolidine derived from aminoindanol has been successfully applied in the asymmetric alkynylation of aldehydes. The ligand is readily available, has a wide substrate scope, and catalyzes the formation of chiral propargylic alcohols with excellent yields and enantioselectivties. Copyright

Synthesis of unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes via alkylidene carbenoid rearrangements

Unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes are synthesized in four steps from commercially available aldehydes or carboxylic acids. The key step in this process involves a Fritsch-Buttenberg-Wiechell rearrangement, in which an alkylidene carbenoid intermediate subsequently rearranges to the desired polyyne. This rearrangement proceeds under mild conditions, and it is tolerant of a range of functionalities. In general, the procedurally facile formation of the dibromoolefinic precursors, in combination with the effectiveness of the rearrangement step, makes this procedure an attractive alternative to traditional methods for di- and triyne synthesis that utilize palladium or copper catalysis.

Modification of the Fritsch-Buttenberg-Wiechell rearrangement: A facile route to unsymmetrical butadiynes

A modification of the Fritsch-Buttenberg-Wiechell rearrangement has been used to form unsymmetrically substituted 1,3-butadiynes from 1,1-dibromo-olefin precursors. The reaction proceeds via lithium-halogen exchange, followed by migration of the aryl or alkynyl moiety to provide the butadiyne framework. The facile formation of the dibromo-olefins in three steps from commercially available aryl aldehydes or carboxylic acid chlorides makes this procedure an attractive alternative to traditional methods for butadiyne synthesis.