35050-46-5

Usage

InChI:InChI=1/C35H46N4O2/c1-9-20-22(11-3)30(18-32-24(13-5)26(15-7)34(40)38-32)36-28(20)17-29-21(10-2)23(12-4)31(37-29)19-33-25(14-6)27(16-8)35(41)39-33/h17-19,36-37H,9-16H2,1-8H3,(H,38,40)/b29-17+,31-19-,32-18-

Upstream product

• 67-56-1 methanol 
• 77469-07-9 3,4-diethyl-5-(3,4-diethyl-5-methylpyrrol-2-ylmethylidene)-3-pyrrolin-2-one 
• 14287-39-9 2,3,7,8,12,13,17,18-octaethyloxophlorin 
• 77469-08-0 3,4-diethyl-5-(3,4-diethylpyrrol-2-ylmethylidene)-3-pyrrolin-2-one 
• 149-73-5 trimethyl orthoformate 
• 16200-52-5 3,4-diethyl-1H-pyrrole 
• 1006-26-4 3,4-diethylpyrrole-2-carbaldehyde 
• 60651-43-6 3,4-diethyl-3-pyrrolin-2-one 

Downstream Products

• 35050-46-5 (E)-octaethyl bilindione 

Relevant academic research and scientific papers

MODELS FOR THE PHOTOREVERSIBILITY OF PHYTOCHROME. Z,E ISOMERIZATION OF CHROMOPEPTIDES FROM PHYCOCYANIN AND PHYTOCHROME.

Chromopeptides which contain linear tetrapyrrole chromophores are prepared by proteolytic digestion of phycocyanin and phytochrome (Pr and Pfr forms).After the nucleophilic addition of mercaptoethanol to C-10 of the tetrapyrrole, irradiation with white light leads to photoisomerization of the tetrapyrrole (Z->E).The products prepared from (Z)-phycocyanin and Pr chromopeptides are similar to Pfr chromopeptides with respect to chromatographic properties, electronic spectra and photolability.It is concluded that the linear tetrapyrrole chromophore of Pr is all-Z whereas Pfr has the E configuration at one of the bridges.

NONHYDROLYTIC CHEMICAL CONVERSION OF OCTAETHYLVERDOHEMOCHROME TO OCTAETHYLBILIVERDIN

Octaethylverdohemochrome, a ferrous oxaporphyrin, was converted to octaethylbiliverdin with the incorporation of an oxygen atom from 18O2 into the latter; this result showed that hydrolysis is not essential for this conversion and that an oxygen-bridged compound cannot be excluded as a precursor of biliverdin.

meso-Reactivity of Porphyrins and Related Compounds. Part 9. Photo-oxygenation of Octaethyloxophlorin

The photo-oxygenation of octaethyloxophlorin has been investigated under basic and under neutral conditions.In both cases unstable intermediate stages are observed spectroscopically.In methanolic sodium methoxide the solution becomes bleached and tetraethyl(methanol)propentdyopent is a significant product.In neutral solutions (e.g. benzene-methanol) the major products are octaethyl-5,15-dioxo-5,15-dihydroporphyrin (4) and octaethyl-19-formyl-21H,24H-bilin-1,15-dione (7), the formation of octaethyl-21H,24H-bilin-1,19-dione (6) being a minor pathway.A mechanistic rationalisation is proposed.

Autoxidation and Solvolysis Products of Octaethylverdohaemochrome

Aerobic degradations of (i) octaethylverdohaemochrome (1) bis(pyridine)iron(II) 2,3,7,8,12,13,17,18-octaethyl-5-oxaporphyrinate in 5percent pyridine-methanol, (ii) octaethylbilindione (2) in the presence of thallium(III) acetate in methanol, (iii) (2) upon t.l.c. have been investigated.These degradations were caused by solvolysis and autoxidation.Eight degradation products obtained from reaction (i) were isolated, and their structures were elucidated by electronic absorption spectrophotometry and mass and n.m.r. spectroscopy as follows: octaethylbilindione (2), 2,3,7,8,12,13,17,18-octaethyl-19-methoxy-21H-bilin-1-one (3), 2,3,7,8,12,13- hexaethyl-14-methoxy-15H,16H-tripyrrin-1-one (4), methyl 2,3,7,8,12,13-hexaethyl-1-oxo-15H,16H-tripyrrin-14-carboxylate (5), 2,3,7,8,12,13-hexaethyl-1-oxo-15H,16H-tripyrrin-14-carbaldehyde (6), (4RS,5RS)- (7) and (4RS,5SR)- 2,3,7,8,12,13,17,18-octaethyl-4,5-dimethoxy-4,5-dihydro-21H,24H-bilin-1,19-dione (8), and 2,3,7,8,12,13-hexaethyl-14-pyridinio-15H,16H-tripyrrin-4-yl tetrafluoroborate (9).The products (6), (7), and (8) obtained from reaction (ii), and (6) obtained from reaction (iii) were identical with those obtained from reaction (i).Both (4RS,5RS)- (7) and (4RS,5SR)-dimethoxy adduct (8) were obtained from reactions (i) and (ii).Only the (4RS,5RS)-ethylenedioxy adduct (10) was obtained when ethylene glycol instead of methanol was used as solvent.

Cyclization of Biliverdins to Verdohaemochromes

Iron(II) octaethylverdohaemochrome was obtained both by cyclization of octaethylbiliverdin in the presence of FeSO4 and pyridine, and by coupled oxidation of octaethylhaemin and ascorbic acid with O2 in the presence of pyridine.The compound obtained by cyclization of biliverdin IXα dimethyl ester was, however, different from that obtained by the methylation of iron(II) protoverdohaemochrome IXα , the product of coupled oxidation of the protohaem in myoglobin.The electronic absorption spectra of the pyridine and tosylmethyl isocyanide (TsCH2NC) complexes, (14) and (15), of the product of cyclization were different from the spectra of the same complexes, (11) and (12), of the product of coupled oxidation.The product of cyclization was reduced to the product of coupled oxidation by sodium dithionite.It is postulated that compounds (14) and (15) are bis(pyridine) and bis(isocyanide) coordination complexes of iron(III) protoverdohaemochrome dimethyl ester.The positions of the maxima in the absorption spectra of compounds (16) and (17), the pyridine and TsCH2NC complexes of both the product of coupled oxidation of mesohaemin dimethyl ester and the product of cyclization of mesobiliverdin dimethyl ester, indicated that these compounds are analogues, not of (11) and (12), but of (14) and (15).Iron(II) azaporphyrins (7) and (13) were prepared by treatment of the corresponding iron(II) oxaporphyrins (5) and (11) with ammonia.

Octaethyl-21H,24H-bilin-1,19-dione (Octaethylbilatriene-abc)

A synthesis of the octaethylbilindione (1) from 3,4-diethylpyrrole is described which is suitable for the preparation of this valuable model compound in quantity.