109459-33-8

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 126-81-8 dimedone 
• 76881-19-1 5,5-dimethyl-3-trifluoromethylsulfonyloxycyclohex-2-en-1-one 

Downstream Products

• 109491-18-1 3-bromo-5,5-dimethylcyclohex-1-en-1-yl triflate 
• 4694-17-1 5,5-dimethlycyclohex-2-en-1-one 

Relevant academic research and scientific papers

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 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.

Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Cycloisomerization/Oxidation of Electron-Deficient Dienynes

A rhodium-catalyzed cycloisomerization and oxidation of tethered dienynes for the synthesis of indanes is described. An auxiliary fragmentation/olefination method (also described herein) provides novel access to tethered alkyne-dienoate substrates. The re

Six-Step Synthesis of Alcyopterosin A, a Bioactive Illudalane Sesquiterpene with a gem-Dimethylcyclopentane Ring

Strategic pairing of ring openings and cycloisomerization provides rapid and efficient "open and shut" entry into sparsely functionalized illudalanes, as exemplified here in the context of a six-step synthesis of alcyopterosin A. Key steps include a tande

Synthesis of "neoprofen", a rigidified analogue of ibuprofen, exemplifying synthetic methodology for altering the 3-D topology of pharmaceutical substances

3,3-Dimethylcyclopentanes (neopentylenes) are ubiquitous in Nature but largely absent from synthetic pharmaceutical libraries. Neopentylenes define a hydrophobic and rigid 3-D topology with distinct molecular pharmacology, as exemplified here with two neo

Thermal Cycloisomerization of Putative Allenylpyridines for the Synthesis of Isoquinoline Derivatives

A cascade (cyclo)isomerization/elimination process produces novel isoquinoline derivatives of potential interest for pharmaceutical, biomedical, and energy-related research. Mechanistic experiments support a putative allenylpyridine (reminiscent of the Garratt-Braverman cyclization) as a key intermediate in the cascade process.

Synthesis, Molecular Pharmacology, and Structure-Activity Relationships of 3-(Indanoyl)indoles as Selective Cannabinoid Type 2 Receptor Antagonists

Synthetic indole cannabinoids characterized by a 2′,2′-dimethylindan-5′-oyl group at the indole C3 position constitute a new class of ligands possessing high affinity for human CB2 receptors at a nanomolar concentration and a good selectivity index. Start

Organic material with high photoelectric property and preparation method thereof

The invention provides an organic material with high photoelectric property, wherein the organic material is a gem-cyclopentane benzothiophene compound, and can be applied to organic electronic devices. Organic light-emitting material and battery cathode material and the like. The structural general formula is as follows. In-flight C1 An aliphatic five-membered or six-membered ring, a geminally-substituted aliphatic five-membered or six-membered ring, or the like is absent. Ar1 Aryl or absent. Ar2 Aryl or absent. The invention provides a gem-cyclopentane-substituted benzothiophene compound with excellent performance, thereby solving the problem of starvation of organic small molecule photoelectric materials, and providing a simple and effective synthetic method for synthesizing substituted benzothiophene based on the novel material.

Synthesis of gem-Dimethylcyclopentane-Fused Arenes with Various Topologies via TBD-Mediated Dehydro-Diels-Alder Reaction

The development of efficient methods for the synthesis of substituted polycyclic arenes with various topologies is in high demand due to their excellent electrical and optical properties. In this work, a series of gem-dimethylcyclopentane-fused arenes with more than ten topologies were synthesized via a 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)-mediated dehydro-Diels-Alder reaction with moderate to good yields. The introduction of the near-planar gem-dimethylcyclopentane moiety not only impacts the molecular conjugative system but also regulates the intermolecular π-πinteractions and crystal packing, which are critical for the photoelectric performance of arenes. The photophysical properties, molecular geometry, molecular packing of these compounds, and electrochemical properties were investigated by UV-vis absorption, fluorescence emission spectra, DFT calculations, single-crystal X-ray structure analysis, and cyclic voltammetry study.

Synthesis of high-value 1,6-enynes by tandem fragmentation/olefination

A tandem process provides high-value 1,6-enynes that are otherwise difficult to prepare. Two base-mediated reactions - fragmentation and olefination - are executed in a coordinated manner that is overall more efficient than either reaction on its own. The