56151-64-5

Usage

Uses

Used in Organic Synthesis:
[1R(1alpha,4abeta,4balpha,10aalpha)]-1,2,3,4,4a,4b,5,6,10,10a-decahydro-7-isopropyl-1,4a-dimethylphenanthren-1-carbonyl chloride is used as a building block in organic synthesis for the formation of new carbon-carbon or carbon-heteroatom bonds. Its unique structure and functional groups allow for the creation of a variety of complex molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, [1R(1alpha,4abeta,4balpha,10aalpha)]-1,2,3,4,4a,4b,5,6,10,10a-decahydro-7-isopropyl-1,4a-dimethylphenanthren-1-carbonyl chloride can be used as a starting material for the development of new pharmaceutical compounds. Its structural features may contribute to the design of novel drugs with specific biological activities.
Used in Materials Science:
[1R(1alpha,4abeta,4balpha,10aalpha)]-1,2,3,4,4a,4b,5,6,10,10a-decahydro-7-isopropyl-1,4a-dimethylphenanthren-1-carbonyl chloride may also find applications in materials science, where its unique properties could be exploited to create new materials with tailored characteristics. The potential for selective reactivity and the presence of various functional groups make it a promising candidate for the development of advanced materials.
Used in Chemical Research:
[1R(1alpha,4abeta,4balpha,10aalpha)]-1,2,3,4,4a,4b,5,6,10,10a-decahydro-7-isopropyl-1,4a-dimethylphenanthren-1-carbonyl chloride can be utilized in chemical research to study reaction mechanisms, explore new synthetic routes, and investigate the properties of related compounds. Its complex structure and potential reactivity make it an interesting subject for scientific inquiry.

Upstream product

• 514-10-3 abietic acid 

Downstream Products

• 631-71-0 ethyl abietate 
• 1182233-33-5 C₂₆H₂₉F₅O₂ 

Relevant academic research and scientific papers

Triterpene and diterpene inhibitors of pyruvate dehydrogenase kinase (PDK)

Several oximes of triterpenes with a 17-β hydroxyl and abietane derivatives are inhibitors of pyruvate dehydrogenase kinase (PDK) activity. The oxime 12 and dehydroabietyl amine 2 exhibit a blood glucose lowering effect in the diabetic ob/ob mouse after a single oral dose of 100 μmol/kg. However, the mechanism of the blood glucose lowering effect is likely unrelated to PDK inhibition.

Design, synthesis, and molecular docking study of new tyrosyl-dna phosphodiesterase 1 (Tdp1) inhibitors combining resin acids and adamantane moieties

In this paper, a series of novel abietyl and dehydroabietyl ureas, thioureas, amides, and thioamides bearing adamantane moieties were designed, synthesized, and evaluated for their in-hibitory activities against tyrosil-DNA-phosphodiesterase 1 (TDP1). The synthesized compounds were able to inhibit TDP1 at micromolar concentrations (0.19–2.3 μM) and demonstrated low cytotox-icity in the T98G glioma cell line. The effect of the terpene fragment, the linker structure, and the adamantane residue on the biological properties of the new compounds was investigated. Based on molecular docking results, we suppose that adamantane derivatives of resin acids bind to the TDP1 covalent intermediate, forming a hydrogen bond with Ser463 and hydrophobic contacts with the Phe259 and Trp590 residues and the oligonucleotide fragment of the substrate.

A new organocatalyst derived from abietic acid and 4-hydroxy-l-proline for direct asymmetric aldol reactions in aqueous media

Enantioselective direct aldol reactions were carried out in aqueous media with a new organocatalyst that was derived from 4-hydroxy-l-proline and abietic acid via a simple and convenient synthetic protocol with a high overall yield (75%). The new organocatalyst was used for aldol reactions between substituted aromatic aldehydes and various ketones in the presence of several acid additives in aqueous media. The corresponding aldol products were obtained in high isolated yields (up to 99%) and with high anti-diastereoselectivities (up to 94%) and enantioselectivities (>99.9%). The catalyst loading can be efficiently reduced to only 1 mol %. The aldol reactions were found to be extremely fast which is very unusual in organocatalyzed reactions in water.

Preparation of fluorinated esters of abietic acid

The reaction of abietic acid chloride with sodium salts of 1H,1H-dihydrotrifluoroethanol, 1H,1H,3H-trihydrotetrafluoropropanol, 1H,1H,5H-trihydrooctafluoropentanol, and pentafluorophenol was studied. The main reaction products are the corresponding fluorinated alkyl (aryl) abietates.

Diterpenoid carboxylic acid anhydrides of the abietane, pimarane, and isopimarane series

Methods were developed for preparation of diterpenoid carboxylic acid anhydrides of the abietane, pimarane, and isopimarane series, the corresponding mixed anhydrides, and mixed anhydrides derived from resin acids and organic or inorganic acids. The resulting anhydrides sharply differ from the parent acids in physical properties; their thermal reactions and isomerizations and the rates of formation and hydrolysis were studied. The data obtained were used to develop new procedures for separation of anhydride mixtures into pure components. Reactions of abietic anhydride with some nucleophilic reagents gave the corresponding esters, ketones, amides, etc. Commercial samples of pine wood resins (gum rosin and tallic rosin) were shown to contain a small amount (0.2%) of diterpenoid anhydride mixtures.

Phytoalexin-like Activity of Abietic Acid and Its Derivatives

Abietic acid and some of its derivatives, not known to be naturally occurring phytoalexins, were examined for their ability to promote H+ conductance across membranes and to inhibit growth of two fungal species-Aphanomyces euteiches and Fusarium moniliforme.These results were compared with those of phaseollin, at phytoalexin isolated from kidney beans.Ion leakage and fungal growth inhibition were shown to be a function of structure, results that suggest that pterocarpan phytoalexin activity requires the presence of a polar, protic functional group situated at the end of a large, rigid hydrophobic moiety.Log P values for phaseollin, abietic acid, and some derivatives of abietic acid were also determined. Keywords: Abietic acid; H+ leakage; antifungal activity; log P; phaseollin

THE INVENTION OF NEW RADICAL CHAIN REACTIONS. PART VIII. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS; A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC ACIDS.

The aliphatic and alicyclic esters of N-hydroxy-pyridine-2-thione are readily reduced by tributylstannane in a radical chain reaction to furnish nor-alkanes.In the absence of the stannane a smooth decarboxylative rearrangement occurs to give 2-substituted thiopyridines.The radicals present in this reaction provoke with t-butylthiol an efficient radical reaction with formation of nor-alkane and 2-pyridyl-t-butyl disulphide.Similarly these carbon radicals can be captured by halogen atom transfer to give noralkyl chlorides, bromides and iodides.With oxygen in the presence of t-butylthiol the corresponding noralkyl hydroperoxides are formed in another radical chain reaction.