55824-09-4

Usage

Uses

Used in Research Applications:
2H-1-Benzopyran-5-ol,2,7-dimethyl-2-(4-methyl-3-pentenyl)is used as a research compound for studying the properties, effects, and potential applications of cannabinoids in various scientific fields.
Used in Forensic Applications:
In the forensic industry, 2H-1-Benzopyran-5-ol,2,7-dimethyl-2-(4-methyl-3-pentenyl)is used as a reference material for the identification and analysis of cannabinoids in legal and criminal investigations.

Upstream product

• 504-15-4 orcinol 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 496-73-1 4-methyl resorcinol 
• 69734-83-4 cannabigerorcinic acid 
• 251654-52-1 3-chloro-2-hydroxy-6-methoxy-4-methylbenzaldehyde 
• 251654-48-5 chloroatranol dimethyl ether 
• 6937-96-8 2,6-dimethoxy-4-methylbenzaldehyde 
• 878479-92-6 methyl 8-chloro-5-methoxy-2,7-dimethyl-2H-chromene-2-acetate 
• 878480-21-8 8-chloro-5-methoxy-2,7-dimethyl-2H-chromene-2-propanonitrile 
• 878479-94-8 8-chloro-5-methoxy-2,7-dimethyl-2H-chromene-2-ethanol 
• 878480-22-9 8-chloro-5-methoxy-2,7-dimethyl-2H-chromene-2-propanal 
• 878480-20-7 8-chloro-2-(2-chloroethyl)-5-methoxy-2,7-dimethyl-2H-chromene 
• 878479-93-7 8-chloro-5-methoxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-chromene 
• 705931-13-1 2,7-dimethyl-5-hydroxy-2-(4-methylpent-3-enyl)-2H-1-benzopyran-6-carboxylic acid 

Relevant academic research and scientific papers

Ortho-Quinone Methide Cyclizations Inspired by the Busseihydroquinone Family of Natural Products

A series of cascade reactions of o-quinone methides have been developed based on the proposed biosynthesis of busseihydroquinone and parvinaphthol meroterpenoid natural products. The polycyclic framework of the most complex family members, busseihydroquinone E and parvinaphthol C, was assembled by an intramolecular [4 + 2] cycloaddition of an electron-rich chromene substrate. The resultant cyclic enol ether underwent rearrangements under acidic or oxidative conditions, which led to a new total synthesis of rhodonoid D.

BIOSYNTHESIS OF PROPYL CANNABINOID ACID AND ITS BIOSYNTHETIC RELATIONSHIP WITH PENTYL AND METHYL CANNABINOID ACIDS

Biosynthesis of propyl cannabinoid acid has been determined by in vitro incubation with a crude enzyme solution from three strains of Cannabis sativa using 14C-labelled cannabinoid acid.Biosynthetic relationships between methyl, propyl and pentyl cannabinoid acids have been demonstrated.Key Word Index-Cannabis sativa; Moraceae; in vitro incubation; propyl cannabinoid acid; biosynthesis.

Synthesis of Cannabinoids: "in Water" and "on Water" Approaches: Influence of SDS Micelles

We have proven that the biomimetic-like synthesis of cannabinoids from citral and the corresponding phenolic counterpart may well be carried out using water as a solvent. The influence of different additives such as surfactants was also analyzed. Rationalization of the reaction mode and regiochemistry of the processes were provided in terms of "on water"and "in water"reactions. The same reactions were conducted in organic media using Ga(III) salts as catalysts. Worthy of being underlined, an unprecedented formal [2+2+2] process was found to occur between two citral molecules and the corresponding phenolic species in both aqueous and organic environments. Computational studies were performed in order to gain a comprehensive mechanistic and energetic understanding of the different steps of this singular process. Finally, the influence of SDS micelles in the chemical behavior of olivetol and citral was also pursued using PGSE diffusion and NOESY NMR studies. These data permitted to tentatively propose the existence of a mixed micelle between olivetol and SDS assemblies.

Total synthesis of rhodonoids a, b, e, and f, enabled by singlet oxygen ene reactions

Singlet oxygen is a versatile reagent for the selective oxidation of organic compounds under mild reaction conditions. It is frequently invoked in biosynthetic pathways, so it is especially suitable for application in the biomimetic synthesis of natural products. Herein, we show that use of the singlet oxygen ene reaction, combined with [2 + 2] cycloadditions, leads to concise, divergent, and redox-economic total syntheses of several polycyclic members of the rhodonoid family of meroterpenoids.

Biomimetic Synthetic Studies on the Bruceol Family of Meroterpenoid Natural Products

A biomimetic approach to total synthesis can offer several benefits, including the development of cascade reactions for the rapid generation of molecular complexity, and guidance in the structure revision of old natural products and the anticipation of ne

One-Pot Total Synthesis of Cannabinol via Iodine-Mediated Deconstructive Annulation

The thermal degradation of cannabichromene (CBC, 3) is dominated by cationic reactions and not by the pericyclic rearrangements observed in model compounds. The rationalization of these differences inspired the development of a process that coupled, in an aromatization-driven single operational step, the condensation of citral and alkylresorciniols to homoprenylchromenes and their in situ deconstructive annulation to benzo[c]chromenes. This process was applied to a total synthesis of cannabinol (CBN, 5) and to its molecular editing.

Biomimetic Cannabinoid Synthesis Revisited: Batch and Flow All-Catalytic Synthesis of (±)-ortho-Tetrahydrocannabinols and Analogues from Natural Feedstocks

Using a combination of Au nanoparticle-catalyzed oxidation under an O2 atmosphere and a Ti-doped montmorillonite (Ti-MMT)-catalyzed tandem arylation/double cyclization, we developed an original and highly selective method for the synthesis of ortho-tetrahydrocannabinol derivatives from simple substrates. The reaction sequence could be performed in two steps in batch mode or in a single operation in continuous-flow reactors. The abnormal regioselectivity was proposed to be the result of the non-innocent role of the MMT support, TiIV cation coordination, and a Lewis acid-assisted Br?nsted acid (LBA) mechanism.

Biomimetic Total Synthesis of Rhodonoids C and D, and Murrayakonine D

A divergent, three-step total synthesis of rhodonoids C and D has been achieved using a biosynthetically inspired, acid-catalyzed cascade cyclization of an epoxy-chromene that involves the presumed intermediacy of o-quinone methides. Application of a similar strategy also allowed synthesis of the alkaloid murrayakonine D.

A Total Synthesis of (±)-Rhododaurichromanic Acid A via an Oxa-[3+3] Annulation of Resorcinols

Development of an oxa-[3+3] annulation of vinyliminium salts with resorcinols as a 1,3-diketo equivalent is described. This annulation constitutes a cascade of Knoevenagel condensation-oxa-electrocyclization leading to a direct access to chromenes. A series of attempts was made to demonstrate its synthetic utility in natural product synthesis, culminating in a total synthesis of (±)-rhododaurichromanic acid A that also featured an intramolecular Gassman-type cationic [2+2] cycloaddition.

Synthetic study for two 2H-chromenic acids, 8-chlorocannabiorcichromenic acid and mycochromenic acid

Two 2H-chromenes having a fully substituted benzene ring, 8-chlorocannabioreichromene (1) and mycochromenic acid (2), were synthesized by a condensation of salicylaldehydes with isopropylidenemalonate or the thermal cyclization of corresponding propargyl ethers.