6728-31-0Relevant articles and documents
Synthesis method of aggregation pheromone (E)-cis-6, 7-epoxy-2-nonenal of Aromia bungii
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Paragraph 0046; 0047; 0048; 0049; 0050; 0051, (2019/05/08)
The invention relates to a synthesis method of aggregation pheromone (E)-cis-6, 7-epoxy-2-nonenal of Aromia bungii, which belongs to the field of pharmaceutical synthesis. The synthesis method comprises the following steps: taking 1, 4-butanediol as a raw material, singly protecting diol with DHP (dihexylphthalate) and then oxidizing TEMPO (tetramethylpiperidine oxide) into 4-((tetrahydro-2H-pyran-2-base) oxy) butyraldehyde; performing a Wittig reaction, so as to obtain (Z)-2-(hepta-4- alkene-1-base-oxy) tetrahydro-2H-pyran; removing the protection of the DHP and oxidizing TEMPO, so as to obtain (Z)-4-heptenal; performing a Wittig reaction, so as to obtain (2E, 6Z)-nona-2, 6-heptadienal; finally, performing epoxidation, so as to obtain the aggregation pheromone (E)-cis-6, 7-epoxy-2-nonenalof the Aromia bungii. The total yield is 6.5%. In the synthesis method, the 1, 4-butanediol with low cost is taken as the starting raw material; the synthesis method has the advantages of being simple in operation and mild in conditions, therefore, the synthesis method is suitable for large-scale preparation.
A study of 1,5-hydrogen shift and cyclization reactions of an alkali isomerized methyl linolenoate
Matikainen, Jorma,Kaltia, Seppo,Ala-Peijari, Maija,Petit-Gras, Ninna,Harju, Kirsi,Heikkil?, Jaakko,Yksj?rvi, Raija,Hase, Tapio
, p. 567 - 573 (2007/10/03)
Heating a mixture formed by alkali isomerization of methyl linolenoate (1) produces a complex mixture with the bicyclic hexahydroindenoic esters 4β-(7-methoxycarbonylheptyl)-5α-methyl-2,3,3aα,4,5, 7aαhexahydroindene (CL5) and 4β-ethyl-5α-(6-methoxycarbonylhexyl)-2,3,3aα,4,5, 7aα-hexahydroindene (CL6) as main components. Similar isomerization reactions of three synthetic model compounds, methyl 9Z,13E,15Z-octadecatrienoate (2), 9Z,14E,16E-octadecatrienoate (4) and 9Z,11E,15Z-octadecatrienoate (5) corroborated the results obtained with alkali isomerized methyl linolenoate.
A New Synthesis of Nona-2E,6Z-dienal
Vig, O. P.,Sharma, M. L.,Gauba, Rita
, p. 313 - 314 (2007/10/02)
Monosodio ethyl malonate on alkylation with 1-bromo-pent-2-yne (III) furnishes the diester (IV) which on decarbethoxylation with NaCl/DMSO, followed by LAH/EtOH reduction of the resultant ester (V), yields the carbinol (VI).Hydrogenation of VI in the presence of Lindlar's catalyst produces hept-4Z-en-1-ol (VII), which on pyridinium chlorochromate oxidation gives the aldehyde (VIII).Wittig-Horner reaction on VIII using ethyl diethylphosphonoacetate produces the dienoate (IX), which on LAH/EtOH reduction followed by oxidation with Corey's reagent, affords the title compound(I).