18500-63-5

Usage

Uses

Used in Pharmaceutical Industry:
7,8-Dihydro-9-methoxy-7,7-dimethyl-6H-cyclopent[g]isoquinoline-5-carboxylic acid is used as a potential therapeutic agent for various medical applications due to its unique chemical properties and biological activities. Its ability to interact with biopolymers and macromolecules makes it a promising candidate for the development of new drugs and treatments.
Used in Chemical Research:
7,8-Dihydro-9-methoxy-7,7-dimethyl-6H-cyclopent[g]isoquinoline-5-carboxylic acid is also utilized in the field of chemical research as a valuable intermediate or building block for the synthesis of more complex molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Natural Products:
As a naturally occurring compound, 7,8-Dihydro-9-methoxy-7,7-dimethyl-6H-cyclopent[g]isoquinoline-5-carboxylic acid can be found in certain plants or fungi, making it a valuable resource for the study and development of natural products with potential medicinal or biological properties.

References

Nair et al., J. Org. Chem., 34, 240 (1969)

InChI:InChI=1/C16H17NO3/c1-16(2)6-10-11(7-16)14(20-3)12-8-17-5-4-9(12)13(10)15(18)19/h4-5,8H,6-7H2,1-3H3,(H,18,19)

Upstream product

• 18500-67-9 illudinine methyl ester 
• 152722-55-9 methyl 7,7-dimethyl-9-methoxy-1,2,3,4,6,7,8-heptahydrocyclopentaisoquinolin-1-one-5-carboxylate 
• 18500-60-2 methyl 7,7-dimethyl-9-methoxy-1,2,3,4,6,7,8-heptahydrocyclopentaisoquinoline-5-carboxylate 

Relevant academic research and scientific papers

Microwave-mediated nickel-catalyzed cyclotrimerization reactions: Total synthesis of illudinine

(Chemical Equation Presented) Rapid and efficient [2 + 2 + 2] cyclotrimerization reactions were discovered through the application of microwave irradiation in conjunction with a Ni(CO)2(PPh 3)2 catalyst. This enables the f

Synthesis of Illudinine from Dimedone and Identification of Activity as a Monoamine Oxidase Inhibitor

The fungal metabolite illudinine is prepared in seven steps and ca. 55% overall yield from dimedone using an open and shut (ring-opening and ring-closing) strategy. Tandem ring-opening fragmentation and olefination of dimedone establishes alkyne and vinylarene functionality linked by a neopentylene tether. Oxidative cycloisomerization then provides the illudinine framework. The key innovation in this second-generation synthesis of illudinine is the use of the nitrile functional group, rather than an ester, as the functional precursor to the carboxylic acid of illudinine. The small, linear nitrile (CN) is associated with improved selectivity, π-conjugation, and reactivity at multiple points in the synthetic sequence relative to the carboxylic acid ester. Preliminary assays indicate that illudinine and several related synthetic analogues are monoamine oxidase inhibitors, which is the first reported indication of biological activity associated with this natural product. Illudinine was found to inhibit monoamine oxidase B (MAO-B) with an IC50of 18 ± 7.1 μM in preliminary assays.

Synthesis of Illudinine from Dimedone

A total synthesis of the illudalane sesquiterpene illudinine was realized in eight steps and 14% overall yield from commercially available dimedone. The approach features tandem fragmentation/Knoevenagel-type condensation and microwave-assisted oxidative

Synthesis of isoquinolines from indanones: Total synthesis of illudinine

Schmidt reaction of 5-methoxy or 7-methoxyindan-1-ones or their derivatives results exclusively in isocarbostyrils which are converted into 6-methoxy or 8-methoxyisoquinolines in good yields.This strategy has been extended to the total synthesis of illudinine methyl ester (1b) starting from methyl 8-methoxy-2,2-dimethyl-7-oxo-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate (4).