4351-03-5

Basic information

• Product Name: (E)-5-cyclohexylidene-2,4-pentadienal
• Synonyms: (E)-5-cyclohexylidene-2,4-pentadienal
• CAS NO: 4351-03-5
• Molecular Weight: 150.221
• Mol File: 4351-03-5.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (E)-5-cyclohexylidene-2,4-pentadienal(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-5-cyclohexylidene-2,4-pentadienal(4351-03-5)
• EPA Substance Registry System: (E)-5-cyclohexylidene-2,4-pentadienal(4351-03-5)

Safety Data

• Hazardous Substances Data: 4351-03-5(Hazardous Substances Data)

Upstream product

• 108-94-1 cyclohexanone 
• 129422-73-7 (5-aza-5-cyclohexylpenta-2,4-dienyl)diethoxyphosphin-1-one 
• 97856-56-9 ethyl (2E)-4-cyclohexylidenebut-2-enoate 
• 190667-85-7 C₁₀H₁₆O 
• 130649-72-8 1-(methylthio)-1-(p-tolylsulfonyl)-1,3-pentadiene 
• 162777-19-7 <(4-methylphenyl)sulfonyl>(trimethylsilyl)methyl methyl sulfide 
• 132760-60-2 5-(methylthio)-5-(p-tolylsulfonyl)-1,3-pentadiene 
• 132760-61-3 1-(methylthio)-5-(p-tolylsulfonyl)-1,3-pentadiene 
• 130649-72-8 (1E,3E)-1-(methylthio)-1-(p-tolylsulfonyl)-1,3-pentadiene 
• 59662-65-6 methylthiomethyl p-tolyl sulfone 
• 110905-37-8 (E)-(4-Oxo-2-butenyl)phosphonsaeure-diethylester 
• 108-91-8 cyclohexylamine 
• 139452-82-7 1-Methyl-4-[1-((1E,3E)-4-methylsulfanyl-buta-1,3-dienyl)-cyclohexanesulfonyl]-benzene 
• 132640-85-8 1-bromo-4-trimethylsiloxy butadiene 

Downstream Products

• 220944-36-5 ethyl (2E,4E)-7-cyclohexyl-2,4,6-heptatrienoate 
• 1334496-35-3 2-((2S,3R,4S,4aS)-3-nitro-4-phenyl-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-yl)acetaldehyde 

Relevant articles and documents

Synthesis of γ,γ-Disubstituted Butenolides through a Doubly Vinylogous Organocatalytic Cycloaddition

A novel organocatalytic approach to γ,γ-disubstituted butenolides is described. It is based on a fully site-selective functionalization of 5-alkylidenefuran-2(5H)-ones via trienamine-mediated [4+2]-cycloaddition with α,β,γ,δ-diunsaturated aldehydes. The developed methodology proceeds with excellent stereocontrol and constitutes a unique example of trienamine chemistry with vinylogous dienophiles. Importantly, the reaction has very broad scope and allows for the introduction of substituents also in the α- or the β-position of the butenolide ring. Usefulness of the products obtained has been confirmed in the intramolecular Stetter reaction leading to polycyclic product.

Exclusive γ-regio functionalization of crotonaldehyde using γ-trimethylsilyl crotonaldimine. Application to the one pot synthesis of conjugated dienals

Cesium fluoride mediated reaction of γ-trimethylsilyl N-tert-butyl crotonaldimine 9 with a wide range of aldehydes takes place in DMSO at room temperature and affords exclusive γ-regio functionalized products. Heating (rt to 100°C) the δ-silyloxy imines 11 thus obtained leads, after very mild hydrolysis of the tert-butylimine function, to the conjugated dienals 14 in good yields and with excellent (E,E)-selectivities.

A New and Convenient Preparation of Conjugated Dienals

For preparation of 5-monosubstituted or 5,5-disubstituted 2,4-dienals, 1-(methylthio)-5-(p-tolylsulfonyl)-1,3-pentadiene (4) is revealed to be an important precursor.When 5-(methylthio)-5-(p-tolylsulfonyl)-1,3-pentadiene, that is easily obtainable from (methylthio)methyl p-tolyl sulfone, was treated with silica gel, 1,5-rearrangement of p-tolylsulfonyl group occurred to give 4.The conditions for mono- or dialkylation of 4 followed by hydrolysis leading to the dienals are desribed.