58506-33-5

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 61, p. 2604, 1996 DOI: 10.1021/jo951923t

Upstream product

• 38447-05-1 (2E,4E)-methyl 5-phenylpenta-2,4-dienoate 
• 39806-16-1 ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate 
• 890022-08-9 ethyl (4E)-5-phenylpenta-2,4-dienoate 
• 100636-30-4 5-phenyl-2,4-pentadienoic acid chloride 
• 107-18-6 allyl alcohol 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 104-53-0 3-phenyl-propionaldehyde 
• 541-41-3 chloroformic acid ethyl ester 
• 14371-10-9 (E)-3-phenylpropenal 
• 100-52-7 benzaldehyde 
• 95728-97-5 (E)-ethyl 3-hydroxy-5-phenylpent-4-enoate 
• 5208-89-9 (E)-1-phenyl-1,4-pentadien-3-ol 
• 24808-73-9 (E)-(3-methoxyprop-1-en-1-yl)benzene 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Downstream Products

• 143816-04-0 (2E,4E)-5-phenylpenta-2,4-dien-1-yl acetate 
• 13466-40-5 (2E, 4E)-5-phenylpenta-2,4-dienal 
• 277332-47-5 Acetic acid 4-((2E,4E)-5-phenyl-penta-2,4-dienyloxy)-phenyl ester 
• 277332-74-8 2-Hydroxy-5-((2E,4E)-5-phenyl-penta-2,4-dienyloxy)-benzoic acid methyl ester 
• 277332-58-8 2-(2,2-Dimethyl-propionyloxy)-5-((2E,4E)-5-phenyl-penta-2,4-dienyloxy)-benzoic acid methyl ester 
• 873424-47-6 (2E,4E)-5-phenylpenta-2,4-dien-1-ylprop-2-yn-1-yl ether 
• 862121-70-8 N-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-5-phenyl-(E,E)-2,4-pentadien-1-amine 

Relevant academic research and scientific papers

Cobalt-Catalyzed Diastereo- And Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates

Catalytic generation of ambiphilic π-allyl-metal complexes and their utility in enantioselective transformations constitutes a powerful approach for introduction of allyl groups to a molecule. Herein an unprecedented cobalt-catalyzed highly site-, diastereo-, and enantioselective protocol for stereoselective formation of nucleophilic allyl-Co(II) complexes followed by addition to aldehydes is presented. The reaction features diastereo- and enantioconvergent conversion of easily accessible allylic alcohol derivatives to diversified enantioenriched homoallylic alcohols with a remarkably broad scope of allyl groups that can be introduced. Mechanistic studies indicated that allyl radical intermediates were involved in this process. These new discoveries establish a new strategy for development of enantioselective transformations through capture of radicals by chiral Co complexes, pushing forward the frontier of Co complexes for enantioselective catalysis.

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

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.

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.

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.

Palladium-catalyzed allylic C-H oxidation under simple operation and mild conditions

We discovered an effective and simple system (Pd/BQ/air/r.t.) for making allylic alcohols through Pd-catalyzed allylic C-H bond functionalization. This approach exhibits advantages due to its simple operation, mild conditions, and environmentally benign features. By modifying reaction conditions, it can be suitable for preparing unsaturated aldehydes, allylic esters, ethers, and amines.

Enantio- A nd regioselective: Ene-reductions using F420H2-dependent enzymes

In the past decade it has become clear that many microbes harbor enzymes that employ an unusual flavin cofactor, the F420 deazaflavin cofactor. Herein we show that F420-dependent reductases (FDRs) can successfully perform enantio-, regio- A nd chemoselective ene-reductions. For the first time, we have demonstrated that F420H2-driven reductases can be used as biocatalysts for the reduction of α,β-unsaturated ketones and aldehydes with good conversions (>99%) and excellent regioselectivities and enantiomeric excesses (>99% ee). Noteworthily, FDRs typically display an opposite enantioselectivity when compared to the well established FMN-dependent Old Yellow Enzymes (OYEs).

SN2″-Selective and Enantioselective Substitution with Unsaturated Organoboron Compounds and Catalyzed by a Sulfonate-Containing NHC-Cu Complex

The first broadly applicable strategy for SN2″-selective and enantioselective catalytic substitution is disclosed. Transformations are promoted by 5.0 mol% of a sulfonate-containing NHC-Cu complex (NHC = N-heterocyclic carbene), and are carried

Palladium-Catalyzed Regioselective Aerobic Allylic C?H Oxygenation: Direct Synthesis of α,β-Unsaturated Aldehydes and Allylic Alcohols

A protocol for the synthesis of α,β-unsaturated aldehydes and allylic alcohols from simple allylic hydrocarbons with water via palladium-catalyzed functionalization of allylic C?H bonds was described. Molecular oxygen is utilized as the sole oxidant in this oxygenation of terminal alkenes. This protocol features good functional group compatibility, broad substrate scope, and high atom- and step-economy. Moreover, the synthetic utility of this method can be highlighted by its application to the synthesis of ibuprofen, which is a highly potent analgesic. (Figure presented.).