109529-98-8

Usage

Uses

Used in Organic Synthesis:
((1E,3E)-5-BROMO-PENTA-1,3-DIENYL)-BENZENE is used as a starting material in organic synthesis for the preparation of various derivatives and analogs. Its unique structure and the presence of the bromine atom make it a versatile compound for creating a wide range of organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, ((1E,3E)-5-BROMO-PENTA-1,3-DIENYL)-BENZENE is used as a reagent in the production of various pharmaceuticals. Its ability to be modified and incorporated into complex molecules makes it a useful component in the development of new drugs.
Used in Agrochemical Production:
((1E,3E)-5-BROMO-PENTA-1,3-DIENYL)-BENZENE is also utilized in the agrochemical industry for the production of various agrochemicals. Its role in creating complex organic compounds contributes to the development of effective and targeted agrochemical products.
Used in Research:
In addition to its practical applications, ((1E,3E)-5-BROMO-PENTA-1,3-DIENYL)-BENZENE is used in research settings to explore its properties and potential applications. Its unique structure and reactivity make it an interesting subject for scientific investigation.

Upstream product

• 39806-16-1 ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate 
• 14371-10-9 (E)-3-phenylpropenal 
• 1552-95-0 ethyl 5-phenyl-2,4-pentadienoate 
• 104-55-2 3-phenyl-propenal 
• 5208-89-9 (E)-1-phenyl-1,4-pentadien-3-ol 
• 13466-40-5 (2E, 4E)-5-phenylpenta-2,4-dienal 
• 38447-05-1 (2E,4E)-methyl 5-phenylpenta-2,4-dienoate 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 58506-33-5 5-phenyl-trans,trans-2,4-pentadien-1-ol 
• 58506-33-5 5-phenylpenta-2,4-dien-1-ol 
• 60329-12-6 2-phenylmethylenecyclopropylmethanol 

Downstream Products

• 1429425-41-1 (R,E)-(3-methylpenta-1,4-dien-1-yl)benzene 
• 39491-62-8 (1E,3E)-hexa-1,3-dien-1-ylbenzene 
• 1021340-56-6 (S,E)-(3-methylpenta-1,4-dien-1-yl)benzene 
• 109898-19-3 (E)-(3-methylpenta-1,4-dien-1-yl)benzene 
• 1581720-36-6 (2S,3S,E)-N-benzyl-2-(dimethylamino)-5-phenyl-3-vinylpent-4-enamide 
• 93039-03-3 (2E,4E)-N,N-dimethyl-5-phenylpenta-2,4-dien-1-amine 

Relevant academic research and scientific papers

Asymmetric Synthesis of Cα-Substituted Prolines through Curtin–Hammett-Controlled Diastereoselective N-Alkylation

Asymmetric synthesis of α-substituted proline derivatives has been accomplished by an efficient chirality-transfer method. High diastereoselectivity of the N-alkylation of the proline ester (C→N chirality transfer) was achieved when a 2,3-disubstituted be

One Stone for Three Birds-Rhodium-Catalyzed Highly Diastereoselective Intramolecular [4+2] Cycloaddition of Optically Active Allene-1,3-dienes

RhCl(PPh3)3-catalyzed [4+2] intramolecular cycloaddition of optically active axially chiral allene-dienes afforded cis-fused [3.4.0]-bicyclic products with three chiral centers in good yields with an excellent chemo- and diastereoselectivity. A pair of enantiomers of such products was generated highly selectively from both enantiomers of starting allene-dienes, indicating that the axial chirality dictated the absolute configurations of the three in situ generated chiral centers with a very high efficiency of chirality transfer.

Stereodivergent Intramolecular C(sp3)-H Functionalization of Azavinyl Carbenes: Synthesis of Saturated Heterocycles and Fused N -Heterotricycles

A general approach for the formation of five-membered saturated heterocycles by intramolecular C(sp3)-H functionalization is reported. Using N-sulfonyltriazoles as Rh(II) azavinyl carbene equivalents, a wide variety of stereodefined cis-2,3-dis

Construction of Silicon-Containing Seven-Membered Rings by Catalytic [4 + 2 + 1] Cycloaddition through Rhodium Silylenoid

A rhodium-catalyzed [4 + 2 + 1] cycloaddition involving 1,3-diene, alkyne, and silylene to afford silicon-containing seven-membered rings was established. In the presence of a rhodium catalyst bearing bis(diphenylphosphino)methane (DPPM), nona-1,3-dien-8-yne derivatives reacted efficiently at 80-110 °C with boryl(isopropoxy)silane or boryl(diethyamino)silane, which reacts as the synthetic equivalent of silylene, to afford 1-silacyclohepta-2,5-dienes (2,5-dihydro-1H-silepines). Regiodivergent and chemo- and stereoselective functionalization of the seven-membered nonconjugated diene was achieved by hydroboration mediated by Cs2CO3 or an iridium catalyst.

Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade

A convenient and efficient domino aryne process was developed under transition-metal-free conditions to generate a range of tetra- and pentacyclic ring systems. This transformation was realized via a 1,2-benzdiyne through a nucleophilic and Diels–Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C?N and two C?C bonds, and two benzofused rings could be constructed concomitantly, which was made possible by distinct chemoselective control at both the 1,2-aryne and 2,3-aryne stages. Moreover, in-depth studies were carried out on the domino aryne precursors and controlling the diastereoselectivity.

Developing glutathione-activated catechol-type diphenylpolyenes as small molecule-based and mitochondria-targeted prooxidative anticancer theranostic prodrugs

Developing concise theranostic prodrugs is highly desirable for personalized and precision cancer therapy. Herein we used the glutathione (GSH)-mediated conversion of 2,4-dinitrobenzenesulfonates to phenols to protect a catechol moiety and developed stable pro-catechol-type diphenylpolyenes as small molecule-based prooxidative anticancer theranostic prodrugs. These molecules were synthesized via a modular route allowing creation of various pro-catechol-type diphenylpolyenes. As a typical representative, PDHH demonstrated three unique advantages: (1) capable of exploiting increased levels of GSH in cancer cells to in situ release a catechol moiety followed by its in situ oxidation to o-quinone, leading to preferential redox imbalance (including generation of H2O2 and depletion of GSH) and final selective killing of cancer cells over normal cells, and is also superior to 5-fluorouracil and doxorubicin, the widely used chemotherapy drugs, in terms of its ability to kill preferentially human colon cancer SW620 cells (IC50 = 4.3 μM) over human normal liver L02 cells (IC50 = 42.3 μM) with a favourable in vitro selectivity index of 9.8; (2) permitting a turn-on fluorescent monitoring for its release, targeting mitochondria and therapeutic efficacy without the need of introducing additional fluorophores after its activation by GSH in cancer cells; (3) efficiently targeting mitochondria without the need of introducing additional mitochondria-directed groups.

Cobalt-catalyzed versus uncatalyzed intramolecular Diels-Alder cycloadditions

The intramolecular [4+2] cycloadditions of dienynes was investigated using cobalt-based catalysts. Substrates without substitution on alkyne moiety were found to react under thermal activation. The use of a cobalt salt as catalyst made reactions cleaner by limiting the formation of byproducts. Cycloadditions with dienynes possessing a substituent on the alkyne pattern occurred only in presence of a cobalt catalyst which displayed a moderate to good activity depending on the substrate patterns.

Access to functionalized imidazolidin-2-one derivatives by Iron-catalyzed oxyamination of alkenes

Functionalized imidazolidin-2-one were prepared by using an iron-catalyzed alkene oxyamination reaction. Hy-droxylamine derivatives were used in this atom-economical process, and the addition of an external oxidant was not required. The conditions developed were shown to be efficient for mono-, di-, and trisubstituted double bonds, and a large scope of diamino alcohol precursors were delivered in good yields with good diastereoselectivities. The mechanistic pathway was studied and appears to involve both a fused aziridine and a carbocationic species.

Discovery of Potent Benzofuran-Derived Diapophytoene Desaturase (CrtN) Inhibitors with Enhanced Oral Bioavailability for the Treatment of Methicillin-Resistant Staphylococcus aureus (MRSA) Infections

Blocking the staphyloxanthin biosynthesis process has emerged as a new promising antivirulence strategy. Previously, we first revealed that CrtN is a druggable target against infections caused by pigmented Staphylococcus aureus (S. aureus) and that naftifine was an effective CrtN inhibitor. Here, we identify a new type of benzofuran-derived CrtN inhibitor with submicromolar IC50 values that is based on the naftifine scaffold. The most potent analog, 5m, inhibits the pigment production of S. aureus Newman and three MRSA strains, with IC50 values of 0.38-5.45 nM, without any impact on the survival of four strains (up to 200 μM). Notably, compound 5m (1 μM) could significantly sensitize four strains to immune clearance and could effectively attenuate the virulence of three strains in vivo. Moreover, 5m was determined to be a weak antifungal reagent (MIC > 16 μg/mL). Combined with good oral bioavailability (F = 42.2%) and excellent safety profiles, these data demonstrate that 5m may be a good candidate for the treatment of MRSA infections.

Copper(I)-Catalyzed Allylic Substitutions with a Hydride Nucleophile

An easily accessible copper(I)/N-heterocyclic carbene (NHC) complex enables a regioselective hydride transfer to allylic bromides, an allylic reduction. The resulting aryl- and alkyl-substituted branched α-olefins, which are valuable building blocks for synthesis, are obtained in good yields and regioselectivity. A commercially available silane, (TMSO)2Si(Me)H, is employed as hydride source. This protocol offers a unified alternative to the established metal-catalyzed allylic substitutions with carbon nucleophiles, as no adaption of the catalyst to the nature of the nucleophile is required.