107586-15-2

Upstream product

• 38846-64-9 2-ethynylbenzaldehyde 
• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 68113-72-4 1-octynylzinc chloride 
• 6630-33-7 ortho-bromobenzaldehyde 
• 629-05-0 n-octyne 

Downstream Products

• 107586-16-3 (E)-6-<2-(oct-1-ynyl)phenyl>hex-5-enoic acid 
• 1199554-77-2 1-[3-(3-methoxyphenyl)-1-naphthyl]-1-heptanone 
• 121221-90-7 1‐ethynyl‐2‐(oct‐1‐yn‐1‐yl)benzene 
• 1613036-46-6 2,2,2-trifluoro-1-(2-(oct-1-yn-1-yl)phenyl)ethanol 
• 102684-52-6 2-(n-Octyl)benzaldehyde 
• 1426121-80-3 C₃₈H₆₂N₂ 
• 1421694-55-4 2-(2-oxooctyl)benzaldehyde 

Relevant academic research and scientific papers

Zinc-Catalyzed Tandem Diels–Alder Reactions of Enynals with Alkenes: Generation and Trapping of Cyclic o-Quinodimethanes (o-QDMs)

A systematic investigation of ZnCl2-catalyzed reactions of enynals with alkenes has been undertaken. Structurally unique propeller-like products could be obtained under mild conditions. Cyclic o-quinodimethanes (o-QDMs) are generated through [4+2] cycloaddition between enynals and alkenes. Both electron-poor and electron-rich dienophiles could be used to trap the active intermediate through [4+2] cycloaddition. But [1,5]-H shift products could also be observed when electron-rich alkenes were used as dienophile. DFT calculations were performed to understand the reaction mechanism. A competition between the [4+2] cycloaddition and [1,5]-H shift was proposed for the transformation of cyclic o-QDMs. The selectivity could be affected by the properties of the substrates. (Figure presented.).

Mechanistic insight into transition metal-catalyzed reaction of enynal/enynone with alkenes: Metal-dependent reaction pathway

A systematic study of the transition metal-catalyzed reaction of enynal/enynone with alkenes has been reported. It was found that the reaction has two metal-dependent reaction pathways. One led to the formation of 1,2-DHN, while another led to cyclic-o-QDM.

Gold Catalysis Meets Materials Science – A New Approach to π-Extended Indolocarbazoles

Herein we describe a modular, convergent synthesis of substituted benzo[a]benzo[6,7]-indolo[2,3-h]carbazoles (BBICZs) using a bidirectional gold-catalyzed cyclization reaction as a key step. A building block strategy enabled the easy variation of substituents at different positions of the core structure and a general analysis of substitution effects on the materials properties of the target compounds. All BBICZs were fully characterized and their optical and electronic properties were studied experimentally as well as by computational methods. Organic thin-film transistors based on eight selected derivatives were fabricated by vacuum deposition and charge-carrier mobilities up to 1 cm2/Vs were measured. (Figure presented.).

Catalytic asymmetric three-component reaction of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate

An efficient enantioselective synthesis of cyclic α-aminophosphonates via multicomponent reactions of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate has been developed with the use of a chiral silver spirocyclic phosphate as the catalyst. This protocol provides straightforward access to a series of chiral C1-phosphonylated 1,2-dihydroisoquinoline derivatives with high yields (up to 99%) and high enantioselectivities (up to 94% ee) for a broad substrate scope. The products could be further transformed into densely functionalized compounds and corresponding α-aminophosphonic acids.

Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives

An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experiments revealed that the cyclization occurs via a 1,5-H shift. The cyclic acetal group promoted the 1,5-H shift by activating the benzylic C-H bond and preventing the migration of the alkoxy group by tethering both alkoxy groups.

Gold-Catalyzed Cyclisation by 1,4-Dioxidation

Amide-substituted diynes were cyclized in the presence of a cationic gold catalyst and an external nucleophile leading to 1-indenones and 1-iminoindenones. The electron-donating features of the nitrogen atom enable the formation of a reactive ketene iminium ion, which can be trapped by either diphenyl sulfoxide or anthranil as nucleophiles in a subsequent oxidation step, providing substituted inden-1-on-3-carboxamides.

Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium

An efficient gold-catalyzed ring-expansion reaction of enyne-lactones to form 2-oxoninonium intermediates is reported. The 2-oxoninonium generated in this work could undergo further 6π electrocyclization and aromatization reaction to produce different aromatic compounds.

Insights into the Gold-Catalyzed Propargyl Ester Rearrangement/Tandem Cyclization Sequence: Radical versus Gold Catalysis - Myers-Saito- versus Schmittel-Type Cyclization

A detailed study of the gold-catalyzed tandem 1,3-carboxy migration/allene-enyne cycloisomerization was undertaken. It was found that after the initial allene formation the selectivity of the reaction is strongly influenced by the polarization of the remaining alkyne. Depending on the substitution pattern of the starting diynes, either a Schmittel- or a Myers-Saito-type cyclization was triggered. The 6-endo-dig Myers-Saito-type cyclization gave access to benzo[b]fluorenes, while the Schmittel pathway (5-exo-dig) delivered benzofulvenes as final products. In special cases a yet unknown pathway was opened by the ambiphilic nature of the allene moiety. In these cases completely different products were obtained by the nucleophilic attack of the alkyne moiety onto the allene that can also act as an electrophile. Mechanistic studies revealed that diradical pathways can be ruled out for this type of tandem cyclization reactions and it is shown that both steps of the reaction cascade are catalyzed by the gold complex.

Bioinspired intramolecular diels-alder reaction: A rapid access to the highly-strained cyclopropane-fused polycyclic skeleton

A bioinsipred gold-catalyzed tandem Diels-Alder/Diels-Alder reaction of an enynal and a 1,3-diene, forming the highly-strained benzotricyclo[3.2.1.0 2,7]octane skeleton, was reported. In contrast, a Diels-Alder/Friedel-Crafts tandem reaction occurred instead when silver salts were used as the catalyst. Although both reactions experienced the similar Diels-Alder reaction of a pyrylium intermediate with a 1,3-diene, they have different reaction mechanisms. The former proceeded with a stepwise Diels-Alder reaction, while the latter one with a concerted one. Mother nature knows best! A gold-catalyzed reaction of enynals and 1,3-dienes, giving rapid access to the highly strained benzotricyclo[3.2.1.02,7]octane skeleton, is reported (see scheme; QMD=quinodimethane). Owing to the mild reaction conditions, excellent substrate scope, and high functional-group tolerance, this system holds potential for the construction of complex molecules with the tricyclo[3.2.1.02,7]octane skeleton. Copyright

Antimycobacterial activity evaluation, time-kill kinetic and 3D-QSAR study of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives

A series of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives were synthesized and evaluated for their antitubercular activity. Some of the compounds exhibited potent activity against Mycobacterium tuberculosis H37Rv. One of the compound having t-butyl at para position of the benzene ring showed excellent activity even better than the standard drug ethambutol with MIC value 1.1 ± 0.2 μM. The time-kill kinetics study of two most active compounds showed rapid killing of the M. tuberculosis within 4 days. Additionally atom-based quantitative structure-activity relationship (QSAR) model was developed that gave a statistically satisfying result (R2) = 0.92, Q2 = 0.75, Pearson-R = 0.96 and effectively predicts the anti-tuberculosis activity of training and test set compounds.