35676-02-9

Usage

Uses

Used in Pharmaceutical Industry:
9-Phenanthrenecarboxylic acid, 2,3,6,7-tetramethoxyis used as an intermediate in the synthesis of (+)-(S)-Tylophorine (T898200), which is a major alkaloid of Tylophora indica. This alkaloid has been recognized for its medicinal properties and potential therapeutic applications, making the compound a valuable component in the development of new drugs and pharmaceutical products.
Used in Chemical Synthesis:
As an intermediate, 9-Phenanthrenecarboxylic acid, 2,3,6,7-tetramethoxyis also used in the chemical synthesis of various other compounds and materials. Its unique structure and functional groups make it a versatile building block for creating a wide range of products, including specialty chemicals, dyes, and other organic compounds.

Upstream product

• 52840-52-5 2,3-bis(3,4-dimethoxyphenyl)acrylic acid 
• 52840-52-5 (E)-2,3-bis(3,4-dimethoxyphenyl)acrylic acid 
• 172922-62-2 (Z)-2,3-bis(3,4-dimethoxyphenyl)propenoic acid 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 25908-89-8 methyl (E)-3,4-dimethoxy-α-(3',4'-dimethoxyphenylmethylene)benzeneacetate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 25908-90-1 methyl 2,3,6,7-tetramethoxyphenanthrene-9-carboxylate 

Downstream Products

• 482-20-2 (S)-(+)-tylophorine 
• 482-20-2 (R)-tylophorine 

Relevant academic research and scientific papers

Seven- and eight-membered heterocyclic biaryl synthesis through a metal-free oxidative coupling reaction

A metal-free intramolecular biaryl coupling mediated by DDQ and BF3·OEt2 was developed. The reaction proceeds smoothly at room temperature to give seven- and eight-membered heterocyclic biaryl compounds in up to 95% yields. Only 1 equiv of DDQ sufficed for the reaction, obviating the use of a large excess of oxidants and undesired chlorination pathway in metal-mediated process.

Active Molybdenum-Based Anode for Dehydrogenative Coupling Reactions

A new and powerful active anode system that can be operated in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) has been discovered. In HFIP the molybdenum anode forms a compact, conductive, and electroactive layer of higher-valent molybdenum species. This system can replace powerful but stoichiometrically required MoV reagents for the dehydrogenative coupling of aryls. This electrolytic reaction is more sustainable and allows the conversion of a broad scope of activated arenes.

Total Synthesis of Phenanthroindolizidine Alkaloids by Combining Iodoaminocyclization with Free Radical Cyclization

A concise and modular synthesis of phenanthroindolizidine alkaloids was achieved by combining iodoaminocylization with a free radical cyclization approach. The route described allowed the preparation of (±)-tylophorine, (±)-antofine, and (±)-deoxypergularinine in six steps. When commercially available l-prolinol was used as a chiral building block, (S)-(+)-tylophorine was also synthesized in 49% yield and >99% ee over five linear steps.

Intramolecular dehydrogenative coupling of 2,3-diaryl acrylic compounds: Access to substituted phenanthrenes

A simple, facile, and environmentally benign intramolecular dehydrogenative coupling of various 1,2-diarylethylenes for the synthesis of phenanthrenes in excellent yield has been described. This new methodology uses ceric ammonium nitrate (CAN) as a promoter at room temperature and has been extended to intermolecular synthesis of biaryl compounds. The electron transfer from methoxyarene to cerium leads to cationic radical formation, which further proceeds to intramolecular coupling. Preliminary mechanistic investigation by EPR spectroscopy and density functional theory calculation suggested a similar view.

Aerobic Oxidative Intramolecular Aromatic Coupling via Heterogeneous Metal Catalysts

An aerobic, heterogeneously catalyzed oxidative intramolecular coupling reaction of aromatic compounds is reported here. Using commercially available, recyclable heterogeneous metal catalysts, the coupling reactions of o-terphenyls and 1,ω-biarylalkanes proceeded quickly under mild conditions, i.e., at room temperature under oxygen as a co-oxidant almost all within 1 h, to provide the corresponding coupled products like triphenylenes and phenanthrenes in good to excellent yields. This reaction is an easily handled, practical, and atom-economical coupling method, which is of great importance in modern organic syntheses. (Figure presented.).

Design, synthesis and biological evaluation of 1-phenanthryl-tetrahydroisoquinoline derivatives as novel p21-activated kinase 4 (PAK4) inhibitors

Functional versatility and elevated expression in cancers have promoted p21-activated kinase 4 (PAK4) as one of the first-in-class anti-cancer drug targets. In this study, a series of novel 1-phenanthryl-tetrahydroisoquinoline analogues have been designed and synthesized as a novel class of small-molecule PAK4 inhibitors to fit into the cavity of PAK4. All of the target compounds were evaluated for their in vitro PAK4 inhibitory activities and antiproliferative activities. Lead optimization identified all the derivatives with more potency than the lead compound, especially compound 21a. Moreover, compound 21a significantly induced the cell cycle in the G1/S phase, and inhibited migration and invasion of MCF-7 cells via the regulation of the PAK4-LIMK1-cofilin signaling pathway. A molecular modeling study showed possible novel binding modes between 21a and PAK4 and provided a structural basis for further structure-guided design of PAK4 inhibitors.

Oxidative intramolecular coupling of 2,3-disubstituted phenyl acrylic acids and derivatives promoted by di-tert-butylperoxide

Polymethoxy-substituted phenanthrene-9-carboxylic acids or their methylate are key intermediates for the synthesis of tylophora alkaloids and their analogs. An intramolecular oxidative coupling reaction of unfunctionalized 2,3-disubstituted phenyl acrylic

An economical and environmentally friendly oxidative biaryl coupling promoted by activated MnO2

An activated manganese dioxide (MnO2)-BF3·OEt2 oxidation system was developed to efficiently mediate the intramolecular as well as intermolecular biaryl coupling. The oxidative coupling proceeds smoothly at ambient temperature to deliver the corresponding five- to eight-membered tricyclic products in good to excellent yields. The employment of the combination of MnO2 and BF3·OEt2 is attractive on the basis of economical and environmental issues.

Iron(III) chloride catalyzed oxidative coupling reaction of 1,2-diarylethylene derivatives

A nontoxic FeCl3 catalyzed intramolecular oxidative coupling reaction was developed for mild synthesis of a series of phenanthrenes with different substituents. The method involves cross dehydrogenative coupling of a variety of 1,2-diarylethyle

A novel sodium nitrite-catalyzed oxidative coupling for constructing polymethoxyphenanthrene rings

An efficient and green oxidative coupling for the direct construction of polymethoxyphenanthrene rings has been developed, which uses environment-friendly sodium nitrite as catalyst and oxygen as terminal oxidant. This methodology also provides an alterna