61447-89-0

Upstream product

• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 106-26-3 cis-3,7-dimethyl-2,6-octadienal 
• 13303-62-3 E-(3,7-dimethylocta-2,6-dienyl)diphenylphosphine oxide 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 292638-85-8 acrylic acid methyl ester 
• 4757-80-6 2,3-Didesoxy-4,5-O-isopropyliden-aldehydo-D-glycero-pent-2-enose 
• 2243-42-7 2-phenoxybenzoic acid 
• 25563-02-4 2-(2-phenoxyphenyl)acetic acid 
• 25562-98-5 2-phenoxybenzyl cyanide 
• 5888-53-9 2-phenoxybenzyl chloride 
• 13807-84-6 (2-phenoxyphenyl)methanol 

Downstream Products

• 61447-97-0 [6-Methyl-4,6-bis-(4-methyl-pent-3-enyl)-cyclohexa-1,3-dienyl]-methanol 
• 61447-91-4 6-Methyl-4,6-bis-(4-methyl-pent-3-enyl)-cyclohex-1-enecarbaldehyde 

Relevant academic research and scientific papers

Diastereoselective synthesis of chiral 1,3-cyclohexadienals

A novel approach to the production of chiral 1,3-cyclohexadienals has been developed. The organocatalysed asymmetric reaction of different β-disubstituted-α,β-unsaturated aldehydes with a chiral α,β-unsaturated aldehyde in the presence of a J?rgensen-Hayashi organocatalyst provides easy and stereocontrolled access to the cyclohexadienal backbone. This method allows for the synthesis of potential photoprotective chiral 1,3-cyclohexadienals and extra extended conjugation compounds in a simple manner.

Intramolecular Aza-Diels-Alder Cyclization of a Dimerized Citral with Anilines Catalyzed by InCl3

A series of aza-polycyles containing octahydroacridine core were prepared via an intramolecular aza-Diels-Alder reaction of a dimerized citral with various aromatic amines. This reaction is efficiently catalyzed by InCl3 at ambient temperature

Synthesis of the Polycyclic Ring Systems of Artocarpol A and D

(Equation Presented) The first synthesis of the polycyclic ring systems of artocarpol A and D has been accomplished. These natural products were isolated recently from the root bark of Artocarpus rigida, and artocarpol A has been shown to have potent anti

A Racemic Diterpene from the Marine Bryozoan Flustra foliacea, Natural Product or Artefact?

A monocyclic diterpene aldehyde, 4.6-bis(4-methylpent-3-en-1-yl)-6-methylcyclohexa-1,3-diene-1-carbaldehyde (1), was isolated from the marine bryozoan Flustra foliacea (L.) by gas phase extraction.The structure was established from extended spectroscopic studies allowing a complete assignment of 1H and 13C NMR spectra.Three isomeric trace diterpenes were detected in the extract.Since 1 was racemic it might arise from condensation of citral occurring during work-up of the extract.In support of this hypothesis, 1 was formed as the main product on base-catalyzed dimerisation of citral in vitro and the three isomeric compounds were formed as by-products or arose from decomposition of 1.

The proline and β-lactoglobulin mediated asymmetric self-condensation of β-ionylideneacetaldehyde, retinal and related compounds

Proline was found to effectively mediate the asymmetric reaction of β-ionylideneacetaldehyde 1A, retinal and related α,β-unsaturated aldehydes to form their corresponding self-condensation products in reasonable enantiomeric excess (up to 65% ee). This sa

Cycloaddition Reaction of Citral with Methyl Acrylate

Reaction of citral with methyl acrylate in the presence of sodium hydride and subsequent work-up in neutral and acidic media afford the cycloaddition products.The structure and stereochemistry of these products have been discussed.

Dimerisation of Citral

3,7-Dimethylocta-2,6-dienal (citral) gives a dimeric product on reaction with sodium hydride in dry ether.The structure and stereochemistry of the product has been discussed.

STEREOCONTROLLED SYNTHESIS OF CONJUGATED POLYENE ISOPRENOIDS USING PHOSPHINE OXIDE ANION INTERMEDIATES

The potential for the Horner-Wittig reaction in the stereocontrolled synthesis of conjugated polyene isoprenoids is investigated.It is shown that metallations of the Z- and E-phosphine oxides (4 and 5), followed by reaction with Z- and E-citrals lead, in single steps, to the corresponding isomeric pentaenes (6) showing complete preservation of the Z- and E-geometries in the starting materials.Although the single step reactions leading to 6 proceed in low overall yields (10-20percent), the olefinations occur with >98percent E-stereoselectivity.Isolation of the intermediate β-hydroxyphosphine oxides (e.g. 14), followed by subsequent treatment with s odium hydride in dimethylformamide, demonstrate that these features of the reaction are associated largely with the remarkably slow rates of elimination from the erythro-intermediates in comparison with the threo-intermediates.Condensation between 4 and the ester-aldehyde (20) leads to the Z-6 ester 21 (34percent).After conversion of 21 into the tetraenal (25), reaction with the phosphine oxide (26), followed by separation of the erythro-β-hydroxy-phosphine oxide intermediate 27 and treatment with NaH in DMF, leads to the di-Z-octaene (28).The octaene 28 shows closely similar spectral data to those found in natural di-Z-phytofluene (2) isolated from fruit of the Tangerine tomato, Lycopersicon escalentum var.In a similar manner, reaction between the Z-phosphine oxide (4) and the dialdehyde (29) produces the di-Z-nonaene (33) which has the same chromophore as that found in di-Z-ζ-carotene (3) from Tangerine tomato fruits.