13697-84-2

Usage

Uses

Used in Fragrance Industry:
2,5-dihydro-3-methylanisole is used as a fragrance ingredient for its sweet, floral, and fruity aroma, enhancing the scent profiles of perfumes and other personal care products.
Used in Flavor and Fragrance Manufacturing:
In the manufacturing of flavors and fragrances, 2,5-dihydro-3-methylanisole serves as a key component to create complex and appealing scents for a variety of consumer goods.
Used in Pharmaceutical Industry:
2,5-dihydro-3-methylanisole has potential applications in the pharmaceutical industry, where its unique properties may contribute to the development of new products or the enhancement of existing ones.
Used in Chemical Industry:
2,5-dihydro-3-methylanisole also finds use in the chemical industry, where it may be employed in the synthesis of other chemicals or as a component in various chemical processes.

InChI:InChI=1/C8H12O/c1-7-4-3-5-8(6-7)9-2/h4-5H,3,6H2,1-2H3

Upstream product

• 4493-67-8 4,5-dimethoxy-1-methylcyclohexa-1,4-diene 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 98677-97-5 3-methoxy-1-methyl-1,3-cyclohexadiene 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 141-52-6 sodium ethanolate 
• 67-56-1 methanol 
• 60-29-7 diethyl ether 

Downstream Products

• 1193-18-6 3-methylcyclohexen-2-one 
• 31883-98-4 3-methylcyclohex-3-en-1-one 
• 2773-58-2 1-methoxy-3-methylenecyclohexene 
• 2161-93-5 1-methoxy-3-methyl-1,3-cyclohexadiene 
• 31236-73-4 1-Methoxy-5-methyl-1-cyclohexen 
• 85944-85-0 1-methoxy-5-methyl-6-pentylcyclohexa-1,4-diene 
• 85944-87-2 6-hexyl-1-methoxy-5-methylcyclohexa-1,4-diene 
• 108185-92-8 4-Bromo-N-[1-methoxy-1-(3-methyl-cyclopent-3-enyl)-meth-(Z)-ylidene]-benzenesulfonamide 
• 591-49-1 1-methylcyclohex-1-ene 
• 591-48-0 3-methyl-1-cyclohexene 
• 88739-07-5 1-methoxy-5-methyl-bicyclo<3.1.0>hexane 
• 702-69-2 7-methyl-1,4-dioxa-spiro[4.5]decan-8-one 
• 102626-22-2 2-Chloro-4-methyl-benzene-1,3,5-tricarbaldehyde 
• 3234-76-2 3-methyl-cyclohex-2-enone-(2,4-dinitro-phenylhydrazone) 

Relevant academic research and scientific papers

Highly Enantioselective Construction of Hajos-Wiechert Ketone Skeletons via an Organocatalytic Vinylogous Michael/Stetter Relay Sequence

A highly enantioselective supramolecular iminium-catalyzed vinylogous Michael addition/Stetter relay sequence has been developed. This transformation provided a series of Hajos-Wiechert-type fused bicyclic diones with three continuous stereogenic centers in good yields with excellent enantioselectivities. The obtained products can be easily transformed into other structures with potential synthetic value.

BENZIMIDAZOLE DERIVATIVES

The invention relates to benzimidazoles of Formula (I) and pharmaceutically acceptable salts thereof, wherein R1 to R6 are as defined in the description; to their use in medicine; to compositions containing them; to processes for their preparation; and to intermediates used in such processes. The benzimidazoles of Formula (I) are ITK inhibitors and are therefore potentially useful in the treatment of a wide range of disorders including, atopic dermatitis.

Rhodium(I)-Catalyzed Enantioselective C(sp3)—H Functionalization via Carbene-Induced Asymmetric Intermolecular C—H Insertion?

Transition-metal-catalyzed C—H insertion of metal-carbene represents an excellent and powerful approach for C—H functionalization. However, despite remarkable advances in metal-carbene chemistry, transition metal catalysts that are capable of enantioselective intermolecular carbene C—H insertion are mainly constrained to dirhodium(II) and iridium(III)-based complexes. Herein, we disclose a new version of asymmetric carbene C—H insertion reaction with rhodium(I) catalyst. A highly enantioselective rhodium(I) complex-catalyzed C(sp3)—H functionalization of 1,4-cyclohexadienes with α-aryl-α-diazoacetates was successfully developed. By using chiral bicyclo[2.2.2]-octadiene as ligand, rhodium(I)-carbene-induced asymmetric intermolecular C—H insertion proceeds smoothly at room temperature, allowing access to a diverse variety of α-aryl-α-cyclohexadienyl acetates and gem-diaryl-containing acetates in good yields with good to excellent enantioselectivities (up to 99% ee). Furthermore, the synthetic utility of the reaction was highlighted by facile synthesis of a novel cannabinoid CB1 receptor ligand. This method may offer a new opportunity for the development of therapeutically exploitable cannabinoid receptor type ligands in medicinal chemistry.

Identification, Synthesis, and Characterization of a Major Circulating Human Metabolite of TRPV4 Antagonist GSK2798745

GSK2798745, an antagonist of the transient receptor potential vanilloid 4 (TRPV4) ion channel, was recently investigated in clinical trials for the treatment of cardiac and respiratory diseases. Human plasma and urine samples collected from healthy volunteers following oral administration were analyzed to identify circulating and excreted metabolites of the parent drug. One major circulating metabolite (1) was found in pooled human plasma samples, accounting for approximately half of the observed drug-related material. Isolation of metabolite 1 from urine samples followed by MS and NMR studies led to a putative structural assignment of 1 where hydroxylation of GSK2798745 occurred on the central ring, producing a penta-substituted cyclohexane structure containing three stereocenters. Two unique chemical syntheses of the proposed structure were developed to confirm the identity of metabolite 1 and provide access to gram quantities for biological characterization.

Design and Synthesis of Natural Product Inspired Libraries Based on the Three-Dimensional (3D) Cedrane Scaffold: Toward the Exploration of 3D Biological Space

A chemoinformatic method was developed to extract nonflat scaffolds embedded in natural products within the Dictionary of Natural Products (DNP). The cedrane scaffold was then chosen as an example of a nonflat scaffold that directs substituents in three-dimensional (3D) space. A cedrane scaffold that has three orthogonal handles to allow generation of 1D, 2D, and 3D libraries was synthesized on a large scale. These libraries would cover more than 50% of the natural diversity of natural products with an embedded cedrane scaffold. Synthesis of three focused natural product-like libraries based on the 3D cedrane scaffold was achieved. A phenotypic assay was used to test the biological profile of synthesized compounds against normal and Parkinson's patient-derived cells. The cytological profiles of the synthesized analogues based on the cedrane scaffold revealed that this 3D scaffold, prevalidated by nature, can interact with biological systems as it displayed various effects against normal and Parkinson's patient-derived cell lines.

Practical synthesis of the C-ring precursor of paclitaxel from 3-methoxytoluene

The practical synthesis of the C-ring precursor of paclitaxel starting from 3-methoxytoluene is described. Lipase-catalyzed kinetic resolution of a substituted cyclohexane-1,2-diol, derived from 3-methoxytoluene in three steps, successfully afforded a desired enantiomer with >99% ee, which was transformed to a cyclohexenone. 1,4-Addition of a vinyl metal species, followed by Mukaiyama aldol reaction with formalin in the presence of a Lewis acid provided the known C-ring precursor of paclitaxel in a 10 g scale.

Tetrahydroindazoles as interleukin-2 inducible T-cell kinase inhibitors. Part II. Second-generation analogues with enhanced potency, selectivity, and pharmacodynamic modulation in vivo

The medicinal chemistry community has directed considerable efforts toward the discovery of selective inhibitors of interleukin-2 inducible T-cell kinase (ITK), given its role in T-cell signaling downstream of the T-cell receptor (TCR) and the implications of this target for inflammatory disorders such as asthma. We have previously disclosed a structure- and property-guided lead optimization effort which resulted in the discovery of a new series of tetrahydroindazole-containing selective ITK inhibitors. Herein we disclose further optimization of this series that resulted in further potency improvements, reduced off-target receptor binding liabilities, and reduced cytotoxicity. Specifically, we have identified a correlation between the basicity of solubilizing elements in the ITK inhibitors and off-target antiproliferative effects, which was exploited to reduce cytotoxicity while maintaining kinase selectivity. Optimized analogues were shown to reduce IL-2 and IL-13 production in vivo following oral or intraperitoneal dosing in mice.

PYRAZOLE CARBOXAMIDE COMPOUNDS, COMPOSITIONS AND METHODS OF USE

Provided herein are compounds of formula (AA): N N H HN O N N R R 6 A (R a ) p, (AA) stereoisomers or a pharmaceutically acceptable salt thereof, wherein A, R a, p, R and R 6 are defined herein, compositions including the compounds and methods of manufacturing and using the compounds for the treatment of diseases.

Property- and structure-guided discovery of a tetrahydroindazole series of interleukin-2 inducible t-cell kinase inhibitors

Interleukin-2 inducible T-cell kinase (ITK), a member of the Tec family of tyrosine kinases, plays a major role in T-cell signaling downstream of the T-cell receptor (TCR), and considerable efforts have been directed toward discovery of ITK-selective inhibitors as potential treatments of inflammatory disorders such as asthma. Using a previously disclosed indazole series of inhibitors as a starting point, and using X-ray crystallography and solubility forecast index (SFI) as guides, we evolved a series of tetrahydroindazole inhibitors with improved potency, selectivity, and pharmaceutical properties. Highlights include identification of a selectivity pocket above the ligand plane, and identification of appropriate lipophilic substituents to occupy this space. This effort culminated in identification of a potent and selective ITK inhibitor (GNE-9822) with good ADME properties in preclinical species.

Increasing the efficiency of the transannular diels-alder strategy via palladium(II)-catalyzed macrocyclizations

Palladium(II)-catalyzed macrocyclizations of bis(vinylboronate ester) compounds are demonstrated to provide a strategically efficient approach to transannular Diels-Alder reaction substrates. In several systems reported, the macrocycle is preorganized such that cycloaddition at room temperature occurs concomitantly with cyclization. Numerous advantages over palladium(0)-catalyzed cross-coupling approaches are demonstrated.