58550-28-0

Basic information

• Product Name: (2E,4E)-ethyl 4-methyl-5-phenylpenta-2,4-dienoate
• Synonyms: (2E,4E)-ethyl 4-methyl-5-phenylpenta-2,4-dienoate
• CAS NO: 58550-28-0
• Molecular Weight: 216.28
• Mol File: 58550-28-0.mol

Chemical Properties

• CAS DataBase Reference: (2E,4E)-ethyl 4-methyl-5-phenylpenta-2,4-dienoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E)-ethyl 4-methyl-5-phenylpenta-2,4-dienoate(58550-28-0)
• EPA Substance Registry System: (2E,4E)-ethyl 4-methyl-5-phenylpenta-2,4-dienoate(58550-28-0)

Safety Data

• Hazardous Substances Data: 58550-28-0(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 107057-89-6 4-methyl-5ξ-phenyl-penta-2ξ,4-dienoic acid 
• 105-36-2 ethyl bromoacetate 
• 101-39-3 2-methyl-3-phenyl-2-propenal 
• 141-78-6 ethyl acetate 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Relevant articles and documents

THE STEREOCHEMISTRY OF THE INTRAMOLECULAR ELECTROPHILIC ATTACK OF AN ALDEHYDE ON A CARBON-TIN BOND

The cyclopentane-forming reaction (20-43) of (4RS,5SR)-2,2,4-trimethyl-5-trimetstannylhexanal takes place with retention of configuration at the carbon atom undergoing electrophilic substitution, in contrast to similar cyclopropane-forming reactions (e.g. 47-48), which take place with inversion of configuration.The hydride transfer (24-45) of the 4RS,5RS diastereoisomeric hexanal takes place from a conformation with hydride anti to the stannyl group.In the case of reacions which might have formed four-membered rings, fragmentation takes place (16-28 and 17-30).The presence of a phenyl ring on the carbon carrying the stannyl group interferes with the reactions designed to test the stereochemistry of the SE2 reaction, diverting the reaction to the formation of tetralins (10-26 and 34-38) or benzcycloheptenes (34-37).

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.

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

LSD1 INHIBITORS AND USES THEREOF

Provided are novel compounds of Formula (I) and pharmaceutically acceptable salts thereof, which are useful for treating a variety of diseases, disorders or conditions, associated with LSDl. Also provided are pharmaceutical compositions comprising the novel compounds of Formula (I), pharmaceutically acceptable salts thereof, and methods for their use in treating one or more diseases, disorders or conditions, associated with LSDl.

cis-Cinnamic acid selective suppressors distinct from auxin inhibitors

The activity of cis-cinnamic acid (cis-CA), one of the allelochemicals, in plants is very similar to that of indole-3-acetic acid (IAA), a natural auxin, and thus cis-CA has long been believed to be an analog of auxin. We have reported some structure-acti

Mechanistic insights in gold-stabilized nonclassical carbocations: Gold-catalyzed rearrangement of 3-cyclopropyl propargylic acetates

The reaction of 3-cyclopropyl propargylic carboxylates with Au(I) and Au(III) catalysts affords selectively 5-(E)-alkylidenecyclopentenyl acetates via [3,3]-sigmatropic rearrangement of the carboxylic moiety followed by cyclopropyl ring opening and cyclization. DFT calculations have been performed, supporting a two-step no-intermediate mechanism along the cyclization coordinate. The stereoselective formation of the exocyclic alkenes is kinetically controlled in the first of these events. Although stereospecific in nature through a gold-stabilized nonclassical carbocation, the chirality transfer in these cyclopentannulations is not complete. Computational and experimental evidence is provided for a Au-promoted cyclopropyl ring opening/epimerization/ring closure in both cis- and trans-cyclopropyl settings, which competes with the cyclization event, thus eroding the stereochemical information transfer. When tertiary acetates were used, products of both 1,2- and 1,3-acyloxy migration processes could be isolated, supporting the competitive coexistence of these two pathways along the reaction profile, as suggested also by DFT calculations.

De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy

(Chemical Equation Presented) The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regi

Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg-Baecklund reaction

A convenient and rapid approach for the synthesis of naturally occurring unsaturated amide alkaloids 1a-1n by the recently developed one-flask Ramberg-Baecklund reaction is described. The starting material was alcohol 3, which was transformed into thiolacetate 4 using the Mitsunobu reaction. In situ cleavage of acetyl moiety of 4, followed by alkylation of the resulting thiol with appropriate chloroacetamide 5, provided the sulfide 6. Oxidation of sulfide 6 gave the corresponding sulfone 2. Treatment of the sulfone 2 with the dibromodifluoromethane in the presence of alumina-supported potassium hydroxide in dichloromethane solution afforded unsaturated amide alkaloids 1a-1n. To the best of our knowledge, the synthesis of 1e and 1i was reported for the first time.

Stereoselective synthesis of substituted all-trans 1,3,5,7-octatetraenes by a modified Ramberg-B?cklund reaction

The reaction of allylic dienylic sulfone with dibromodifiuoromethane in the presence of alumina-supported KOH in dichloromethane solution results in facile rearrangement affording the corresponding all-trans 1,3,5,7-octatetraenes in excellent yields. This result shows that the double bonds of stereochemically defined allylic dienylic sulfone retain their stereochemistry and the newly formed double bond has an (E)-configurafion in the modified Rambeig-B?cklund procedure.

Novel Synthesis of Phenol Derivatives by Palladium-Catalyzed Cyclocarbonylation of 2,4-Pentadienyl Acetates

Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140 deg C under 50 atm of CO.No five-membered ring products were observed.A platinum complex PtCl2(PPh3)2 was also effective as a catalyst.The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3,5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51percent yield on heating to 160 deg C under 50 atm of CO in the presence of NEt3 and Ac2O.Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates.On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO, respectively.