104293-07-4

Usage

Uses

Used in Organic Synthesis:
1-Bromo-4-(3-chloro-propenyl)-benzene is used as a building block in the synthesis of various organic compounds, including dyes and fragrances, due to its unique chemical structure and reactivity.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1-Bromo-4-(3-chloro-propenyl)-benzene is used as an intermediate in the synthesis of a range of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Production:
1-Bromo-4-(3-chloro-propenyl)-benzene is also utilized in the agrochemical sector, serving as a key intermediate in the production of various agrochemicals that aid in crop protection and enhancement of agricultural yields.
Safety Considerations:
Due to its potentially hazardous nature, 1-Bromo-4-(3-chloro-propenyl)-benzene should be handled with caution. It is known to cause skin and eye irritation and can be harmful if ingested or inhaled, necessitating proper safety measures during its use and storage.

Upstream product

• 1200-07-3 trans-4-bromocinnamic acid 
• 3650-78-0 methyl (E)-4-bromocinnamate 
• 37614-58-7 3-(4-bromophenyl)prop-2-yn-1-ol 
• 589-87-7 1,4-bromoiodobenzene 
• 24393-53-1 ethyl (E)-3-(4-bromophenyl)-2-propenoate 
• 1122-91-4 4-bromo-benzaldehyde 
• 105515-33-1 (2E)-3-(4-bromophenyl)prop-2-en-1-ol 

Downstream Products

• 38276-70-9 3'-(p-Bromphenyl)-allyl-4-methylphenylether 
• 105515-33-1 3-(4-bromophenyl)prop-2-en-1-ol 
• 58824-56-9 1-(p-bromophenyl)prop-2-en-1-ol 
• 1214913-12-8 [1-(4-bromophenyl)allyl]dimethylphenylsilane 
• 1464149-52-7 (E)-(3-(4-bromophenyl)allyl)(trifluoromethyl)sulfane 

Relevant academic research and scientific papers

Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes

Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. We report a photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes. Quantum mechanical calculations (uM06-2X and DLPNO), including TD-DFT calculations, and experimental studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cla￠ radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. We anticipate that the use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity.

Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal

Herein, we report a Cu-catalyzed enantioselective allylic alkylation using a γ-butyrolactone-derived silyl ketene acetal. Critical to the development of this work was the identification of a novel mono-picolinamide ligand with the appropriate steric and electronic properties to afford the desired products in high yield (up to 96 %) and high ee (up to 95 %). Aryl, aliphatic, and unsubstituted allylic chlorides bearing a broad range of functionality are well-tolerated. Spectroscopic studies reveal that a CuI species is likely the active catalyst, and DFT calculations suggest ligand sterics play an important role in determining Cu coordination and thus catalyst geometry.

Comprehensive structure-activity-relationship of azaindoles as highly potent FLT3 inhibitors

Acute myeloid leukemia (AML) is characterized by fast progression and low survival rates, in which Fms-like tyrosine kinase 3 (FLT3) receptor mutations have been identified as a driver mutation in cancer progression in a subgroup of AML patients. Clinical trials have shown emergence of drug resistant mutants, emphasizing the ongoing need for new chemical matter to enable the treatment of this disease. Here, we present the discovery and topological structure-activity relationship (SAR) study of analogs of isoquinolinesulfonamide H-89, a well-known PKA inhibitor, as FLT3 inhibitors. Surprisingly, we found that the SAR was not consistent with the observed binding mode of H-89 in PKA. Matched molecular pair analysis resulted in the identification of highly active sub-nanomolar azaindoles as novel FLT3-inhibitors. Structure based modelling using the FLT3 crystal structure suggested an alternative, flipped binding orientation of the new inhibitors.

Palladium-catalyzed oxidative arylacetoxylation of alkenes: Synthesis of indole and indoline derivatives

A method for the oxidative arylacetoxylation of alkenes has been developed to synthesize indole and indoline derivatives from readily accessible substrates. The cinnamyl tethered anilines with picolinamide as a directing group provided 3-substituted indoles via intramolecular oxidative arylacetoxylation, and the 2-methyl substituted cinnamyl anilines furnished indoline derivatives with 3-position quaternary stereocenters in good to excellent yields via sequential intramolecular oxidative arylacetoxylation, hydrolysis and oxidation steps.

Divergent Gold(I)-Catalyzed Skeletal Rearrangements of 1,7-Enynes

The gold(I) complex catalyzed cycloisomerization and skeletal rearrangement of 1,n-enynes (n=5-7) is a powerful methodology for the efficient synthesis of complex molecular architectures. In contrast to 1,6-enynes, readily accessible homologous 1,7-enynes are largely unexplored in such transformations. Here, the divergent skeletal rearrangement of all-carbon 1,7-enynes by catalysis with a cationic gold(I) complex is reported. Depending on electronic and steric factors, differently substituted 1,7-enynes react via different carbocations formed from a common gold carbene intermediate to yield on the one hand novel exocyclic allenes and on the other hand tricyclic hexahydro-anthracenes through a novel dehydrogenative Diels-Alder reaction. Two birds with a gold-stone! Divergent gold(I) catalysis unraveled a novel cycloisomerization and a dehydrogenative Diels-Alder reaction of 1,7-enynes.

Rhodium(ii)-catalyzed intramolecular formal [4 + 3] cycloadditions of dienyltriazoles: Rapid access to fused 2,5-dihydroazepines

Rhodium(ii)-catalyzed intramolecular [4 + 3] cycloadditions of dienyltriazoles have been developed, which enable the efficient synthesis of various fused 2,5-dihydroazepines. Mechanistically, the titled reaction proceeds via an interesting tandem cyclopropanation/aza-cope rearrangement.

A chiral sulfoxide-ligated ruthenium complex for asymmetric catalysis: Enantio- and regioselective allylic substitution

The design and synthesis of a novel chiral sulfoxide-ligated cyclopentadienyl ruthenium complex is described. Its utility as an asymmetric variant of [CpRu(MeCN)3]PF6 is demonstrated through its ability to function in the branched-selective asymmetric allylic alkylation of phenols and carboxylic acids. Water has also been shown to act as a competent nucleophile in this reaction to generate branched allyl alcohols with good regio- and enantioselectivities.

Expedient access to branched allylic silanes by copper-catalysed allylic substitution of linear allylic halides

An unprecedented copper-catalysed allylic transposition enables the regioselective synthesis of branched allylic silanes from linear allylic halides through direct C-Si bond formation.

Ruthenium-catalyzed synthesis of allylic alcohols: Boronic acid as a hydroxide source

Secondary allylic alcohols were synthesized from linear allylic halides or carbonates using a catalytic amount of a ruthenium complex in the presence of boronic acid. The effects of solvent, base, ruthenium precursor, and boronic acid were fully explored, and the scope of the reaction was extended to various sub-strates. We also describe a preliminary investigation towards an enantioselective process.

NOVEL ALKYNE COMPOUNDS HAVING AN MCH-ANTAGONISTIC EFFECT, AND MEDICAMENTS CONTAINING SAID COMPOUNDS

The invention relates to alkyne compounds of general formula (I), wherein the groups and radicals A, B, W, X, Y, Z, R1, and R2 have the meanings indicated in claim 1. The invention further relates to medicaments containing at least one inventive alkyne. The disclosed medicaments are suitable for the treatment of metabolic disorders and/or eating disorders, particularly adiposity and diabetes, as a result of the MCH receptor antagonistic activity thereof.