129113-00-4

Usage

Uses

2-Ethynyl-6-methoxynaphthalene (cas# 129113-00-4) is a compound useful in organic synthesis.

InChI:InChI=1/C13H10O/c1-3-10-4-5-12-9-13(14-2)7-6-11(12)8-10/h1,4-9H,2H3

Upstream product

• 129112-99-8 2-methyl-4-(6-methoxynaphthalen-2-yl)but-3-yn-2-ol 
• 454431-03-9 1-(6-methoxy-2-naphthyl)-2-trimethylsilylacetylene 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 54828-56-7 2--(6--methoxynaphthalen--2--yl)acetaldehyde 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 1066-54-2 trimethylsilylacetylene 
• 3900-45-6 6-methoxy-2-acetylnaphthalene 

Downstream Products

• 144406-11-1 2-(6-Methoxy-naphthalen-2-yl)-acrylic acid p-tolyl ester 
• 23981-80-8 naproxen 
• 3453-40-5 3-(6-methoxynaphthalen-2-yl)propionic acid 
• 306973-74-0 (1S,2S,5R)-2-i-propyl-5-methyl-1-[2-(6-methoxynapht-2-yl)-1-ethyn-1-yl]cyclohexan-1-ol 
• 919363-67-0 C₃₆H₃₀N₈O₅ 
• 1021168-41-1 (3R,4S,5R)-3,4-diacetoxy-5-[(6-methoxynaphthalen-2-yl)ethynyl]-1-benzyl-2-pyrrolidinone 
• 1033193-36-0 2-methoxy-6-(3-phenyl-1-butynyl)naphthalene 
• 1070440-33-3 C₂₉H₃₈O₅ 
• 1073760-38-9 (E)-N,N'-dicyclohexyl-3-(6-methoxynaphthalen-2-yl)propiolamidine 
• 1114548-01-4 (Z)-N-(3-(6-methoxynaphthalen-2-yl)prop-2-ynylidene)cyclohexanamine 
• 1133437-59-8 1-benzyl-2-(2-(2-methoxynaphthalen-6-yl)ethynyl)pyrrolidine 
• 1161747-26-7 3-dibenzylamino-5-(6-methoxy-naphthalen-2-yl)-pent-4-ynoic acid ethyl ester 
• 1186122-82-6 C₂₀H₁₆O₃ 

Relevant academic research and scientific papers

Design of an extremely high birefringence nematic liquid crystal based on a dinaphthyl-diacetylene mesogen

We designed dinaphthyl-diacetylene-based nematic liquid crystals with alkoxy tails (DNDA-OCm) and evaluated their birefringence (Δn). Actual measurements of pure target compounds showed that DNDA-OC2 had the highest value of 0.62 at 550 nm at Tc + 10 °C.

Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel-Catalyzed Cascade Reactions: Facile Synthesis of Profens

We report a stereoselective conversion of terminal alkynes to α-chiral carboxylic acids using a nickel-catalyzed domino hydrocarboxylation-transfer hydrogenation reaction. A simple nickel/BenzP* catalyst displayed high activity in both steps of regioselective hydrocarboxylation of alkynes and subsequent asymmetric transfer hydrogenation. The reaction was successfully applied in enantioselective preparation of three nonsteroidal anti-inflammatory profens (>90 % ees) and the chiral fragment of AZD2716.

Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products

Conversion of the numerous aryl ketones into aryl electrophiles via Ar-C(O) cleavage remains a challenging yet highly desirable transformation in Sonogashira-type coupling. Herein, we report a palladium-catalyzed ligand-promoted alkynylation of unstrained aryl ketones. The protocol allows the alkynylation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope. The potential applications of this protocol in drug discovery and chemical biology are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products. More importantly, two different biologically important fragments derived from a pharmaceutical and natural product could be connected by the consecutive alkynylation of ketones. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynylation.

Micelle-Mediated Trimerization of Ynals to Orthogonally Substituted 4H-Pyrans in Water: Downstream Rearrangement to Bioactive 2,8-dioxabicyclo[3.3.1]nona-3,6-diene Frameworks

An efficient trimerization of ynals to diversely substituted 4H-pyran constructs has been executed in water, under ambient conditions employing micellar catalysis. The method is in agreement with the ideas of green and sustainable chemistry. The locus of the micellar reaction site has been probed through proton NMR studies. A general acid-mediated downstream rearrangement of the derived 4H-pyrans to interesting 2,8-dioxabicyclo[3.3.1]nona-3,6-dienes has been observed.

Fluorine-containing dinaphthylacetylene liquid crystal compound, preparation method and application thereof

The invention relates to a fluorine-containing dinaphthylacetylene liquid crystal compound, which has a structural formula shown as the specification. Specifically, R is respectively independent straight chain alkyl of C1-9. The fluorine-containing dinaphthylacetylene liquid crystal compound provided by the invention has the advantages of low melting point, high clearing point, and high birefringence, etc., and can be used for preparation of high birefringence liquid crystal materials with good performance.

2-Aryl-8-aza-3-deazaadenosine analogues of 5′-O-[N-(salicyl)sulfamoyl]adenosine: Nucleoside antibiotics that block siderophore biosynthesis in Mycobacterium tuberculosis

A series of 5′-O-[N-(salicyl)sulfamoyl]-2-aryl-8-aza-3-deazaadenosines were designed to block mycobactin biosynthesis in Mycobacterium tuberculosis (Mtb) through inhibition of the essential adenylating enzyme MbtA. The synthesis of the 2-aryl-8-aza-3-deaz

Time-dependent solid-state polymorphism of a series of donor-acceptor dyads

In order to exploit the use of favorable electrostatic interactions between aromatic units in directing the assembly of donor-acceptor (D-A) dyads, the present work examines the ability of conjugated aromatic D-A dyads with symmetric side chains to exhibit solid-state polymorphism as a function of time during the solid formation process. Four such dyads were synthesized, and their packing in the solid state from either slower (10-20 days) or faster (1-2 days) evaporation from solvent was investigated using single crystal X-ray analysis and powder X-ray diffraction. Two of the dyads exhibited tail-to-tail (A-A) packing upon slower evaporation from solvent and head-to-tail (D-A) packing upon faster evaporation from solvent. A combination of single-crystal analysis and XRD patterns were used to create models, wherein a packing model for the other two dyads is proposed. Our findings suggest that while side chain interactions in asymmetric aromatic dyads can play an important role in enforcing segregated D-A dyad assembly, slowly evaporating symmetrically substituted aromatic dyads allows for favorable electrostatic interactions between the aromatic moieties to facilitate the organization of the dyads in the solid state.

Amino derivatives of indolone-N-oxide: Preparation and antiplasmodial properties

There is an urgent need for new antimalarial drugs with novel mechanisms of action on novel targets. Indolone-N-oxides (INODs) display antimalarial properties in vitro and in vivo, but identified leads such as 6-(4-chloro-phenyl)-5-oxy-[1,3]dioxolo[4,5-f]

Aerobic oxynitration of alkynes with tBuONO and TEMPO

An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.

Unique solvent-dependent fluorescence of nitro-group-containing naphthalene derivatives with weak donor-strong acceptor system

We synthesized nitro-group-containing π-conjugated naphthalene derivatives with a weak donor-strong acceptor system and investigated their photophysical properties. The nitro group was introduced into naphthalene through the phenyl or phenylethynyl moiety at the C2 and C7 positions as the strong acceptor moiety, and a methoxy group was introduced into naphthalene directly at the position opposite to the nitro group, as a weak donor moiety. While 2-(4-nitrophenyl)naphthalene did not show fluorescence in various solvents, 2-methoxy-6-(4-nitrophenyl)naphthalene showed fluorescence in weakly polar solvents (ΦF = 0.11 in CH2Cl2), with a large Stokes shift (Δν = 12,000 cm-1). Additionally, 2-methoxy-6-(4-nitrophenyl)naphthalene did not show fluorescence in polar solvents (acetonitrile) and non-polar solvents (toluene). This unique solvent-dependent fluorescence is remarkable for environmental fluorescence sensor applications.