462637-40-7

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-(hex-1-yn-1-yl)benzoate is used as an intermediate in the synthesis of Apigenin 5-O-β-D-Glucuronide, which has potential applications in the development of cancer therapeutics. Apigenin 5-O-β-D-Glucuronide has been reported to induce the reversion of transformed phenotypes of v-H-ras-transformed NIH 3T3 cells at low concentrations by inhibiting MAP kinase activity. Additionally, it inhibits the proliferation of malignant tumor cells by G2/M arrest and induces morphological differentiation.
Furthermore, Apigenin has been reported to enhance the gap junction intracellular communication in liver cells, which may contribute to its potential use in liver-related therapies. The synthesis of Apigenin 5-O-β-D-Glucuronide through the use of Methyl 2-(hex-1-yn-1-yl)benzoate could lead to the development of novel treatments for various types of cancer and liver disorders.

Upstream product

• 610-94-6 2-bromobenzoic acid methyl ester 
• 693-02-7 hex-1-yne 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 33775-94-9 2-(methylthio)iodobenzene 
• 88-67-5 2-Iodobenzoic acid 

Downstream Products

• 609358-79-4 3-[2-(hex-1-ynyl)phenyl]pentan-3-ol 
• 599-69-9 N,N,4-trimethylbenzenesulfonamide 
• 120870-47-5 2-(1-hexyn-1-yl)benzoic acid 
• 1314961-21-1 3-n-butyl-4-(phenylselenyl)-1H-isochromen-1-one 
• 1357469-14-7 (2E)-3-phenylprop-2-en-1-yl 2-hex-1-yn-1-ylbenzoate 
• 1357469-19-2 furan-2-ylmethyl 2-hex-1-yn-1-ylbenzoate 
• 30531-69-2 3-butylisochromen-1-one 
• 1357469-28-3 3-butyl-4-[(2E)-3-phenylprop-2-en-1-yl]-1H-isochromen-1-one 
• 1357469-30-7 4-benzyl-3-butyl-1H-isochromen-1-one 
• 1558764-09-2 (Z)-methyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-enyl)benzoate 
• 1609250-67-0 cis-methyl-2-(hex-1-en-1-yl)benzoate 
• 1311408-35-1 trans-methyl-2-(hex-1-en-1-yl)benzoate 
• 294190-48-0 2-(1-hexyn-1-yl)-N-methoxy-N-methylbenzamide 
• 1082852-48-9 (E)-3-(1,1-diphenylhexan-2-ylidene)isobenzofuran-1(3H)-one 

Relevant academic research and scientific papers

Gold-Catalyzed Amide/Carbamate-Linked N, O-Acetal Formation with Bulky Amides and Alcohols

A gold-catalyzed N,O-acetal formation was established to construct an amide/carbamate-linked N,O-acetal substructure with bulky alcohols. The acyliminium cation species generated from o-alkynylbenzoic acid ester in the presence of a gold catalyst is highly reactive and underwent nucleophilic attack of various bulky alcohols and phenols at room temperature under neutral conditions, leading to the corresponding N,O-acetals in yields of 34-89% with good functional group tolerance.

Borylative Heterocyclization without Air-Free Techniques

In contrast to previously reported borylative heterocyclization methods, a reaction here proceeds without air-free techniques to access synthetically useful borylated thiophenes, benzothiophenes, and isocoumarins. A comparison of stability/decomposition rates in air of several catecholboronic ester (Bcat) compounds derived from different heterocycle cores showed a strong dependence on the heterocycle structure. Lessons learned from this comparison were then harnessed for the development of borylative heterocyclization reactions under ambient-atmosphere conditions and with wet solvent. In contrast to literature reports suggesting general moisture sensitivity, a subset of Bcat products resulting from this technique were chromatography-stable and directly isolable, obviating the requirement for an extra synthetic transformation into more stable boron species, such as pinacolboronic esters (Bpin), for isolation. The isolated Bcat products were amenable to various downstream functionalization reactions, including reactions that were not accessible with their better-known Bpin counterparts, showing the complementarity of Bcat reaction partners and expanding their known chemistry. These results suggest the value of conceptual revisitation of substitution and solvent influence on stability and isolability of organo-Bcat compound classes and lay the groundwork for development of additional practical borylative methods in air.

Copper-Catalyzed Modular Access to N-Fused Polycyclic Indoles and 5-Aroyl-pyrrol-2-ones via Intramolecular N—H/C—H Annulation with Alkynes: Scope and Mechanism Probes

Copper-catalyzed intramolecular N—H/C—H annulation with alkynes has been developed. A variety of densely functionalized heterocycles, such as pyrrolo[1,2-a]indoles, indolo[1,2-c]quinazolin-2-ones, oxazolo[3,4-a]indoles, and imidazo[1,5-a]indoles, were synthesized in an atom- and step-economical manner, owing to the high modularized feature of aniline moiety, the linker moiety, as well as the alkyne moiety. By simply changing the oxidant from di-tert-butyl peroxide (DTBP) to 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), the reaction could readily be transformed to the aminooxygenation pathway, which grabs one oxygen atom from the TEMPO to generate 5-aroyl-pyrrol-2-ones. Mechanistic experiments indicate that vinyl radical is involved in this reaction and an amidyl-radical-initiated radical cascade might be responsible for this transformation.

Continuous Electrochemical Synthesis of Iso-Coumarin Derivatives from o-(1-Alkynyl) Benzoates under Metal- and Oxidant-Free

A non-oxidant and metal-free strategy for synthesizing iso-coumarin by using a continuous electrochemical microreactor to initiate an oxidative cyclization reaction of o-(1-alkynyl) benzoate and radicals. This efficient and clean continuous electrosynthesis method not only avoids the complicated gas protection operation and production of by-products in the batch processes, but also help to overcome the difficulty that batch metal catalysis and electrocatalysis are difficult to scale up, and has the potential for pilot-scale experiment.

Gold(i)-catalyzed Nicholas reaction with aromatic molecules utilizing a bifunctional propargyl dicobalt hexacarbonyl complex

A benchtop-stable reagent for the catalytic Nicholas reaction was developed. By combining a propargyl dicobalt hexacarbonyl cluster with an ortho-alkynylbenzoate unit and a fluorous tag, introduction of a propargyl hexacarbonyl complex on various aromatic compounds having acid- or base-sensitive functional groups becomes possible by using a gold(i) catalyst. In addition, the presence of a fluorous tag facilitates convenient separation of the target products from byproducts.

Gold-catalyzed Rapid Construction of Nitrogen-containing Heterocyclic Compound Library with Scaffold Diversity and Molecular Complexity

1,3-unsubstituted 2-(1H-indol-2-yl)ethanamines were employed for the first time to react with alkynoic acids (AAs) to achieve gold-catalyzed highly selective cascade reactions to furnish novel indole-fused skeletons. Furthermore, with this powerful gold catalytic system, a library of indole/pyrrole/thiophene/benzene/naphthalene/pyridine-based nitrogen-containing heterocyclic compounds (NCHCs) with scaffold diversity and molecular complexity was constructed rapidly using various amine nucleophiles (ANs) and diverse AAs as the building blocks. This general protocol features excellent selectivity, extraordinarily broad substrate scope, readily available inputs, good to high yields, high bond-forming efficiency, and step economy, thus providing a facile and efficient access to a variety of valuable nitrogen-containing heterocycles.

Metal-Free Synthesis of 4-Chloroisocoumarins by TMSCl-Catalyzed NCS-Induced Chlorinative Annulation of 2-Alkynylaryloate Esters

4-Chloroisocoumarins can be conveniently prepared from 2-alkynylaryloate esters via the activation of alkynes by electrophilic chlorine, generated in situ from N-chlorosuccinimide (NCS) in the presence of 10 mol % trimethylsilyl chloride (TMSCl), which leads to 6-endo-dig-selective chlorinative annulation to give the desired products in moderate to quantitative yields. The procedure employs readily available reagents and can be conveniently carried out on a wide scope of substrates under mild conditions (0 °C to rt). Furthermore, the reaction is scalable for gram-scale preparation of 4-chloroisocoumarins. Additionally, 4-bromo- and 4-iodoisocoumarins can be prepared in moderate to good yields by replacing NCS with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS), respectively.

Gold promoted arylative cyclization of alkynoic acids with arenediazonium salts

Alkynoic acids derived from salicylic acid and analogues undergo arylative cyclization with arenediazonium salts promoted by gold in the absence of external ligands. The reaction is thermally induced and proceeds even in the absence of light. A difference in regioselectivity has been found compared with that observed in the cycloisomerization process of the same type of compounds.

Divergent Syntheses of (Z)-3-Alkylideneisobenzofuran-1(3 H)-ones and 1 H-Isochromen-1-ones by Copper-Catalyzed Cycloisomerization of 2-Alkynylbenzoic Acids in Ionic Liquids

The cycloisomerization of readily available 2-alkynylbenzoic acids 1 in ionic liquids (ILs) as recyclable reaction media has been studied under the catalytic action of CuCl2. With substrates bearing an aryl group on the triple bond, a mixture o

Divergent syntheses of iodinated isobenzofuranones and isochromenones by iodolactonization of 2-alkynylbenzoic acids in ionic liquids

The regiochemical outcome of the iodolactonization of 2-alkynylbenzoic acids, carried out at 100 °C in ionic liquids (ILs) as unconventional solvents and with molecular iodine as the iodine source, in the absence of external bases, was found to be strongl