67674-37-7Relevant academic research and scientific papers
PROCESS FOR PREPARING A 5-ALKEN-1-YNE COMPOUND, (6Z)-1,1-DIALKOXY-6-NONEN-2-YNE COMPOUND, (2E,6Z)-2,6-NONADIENAL AND (2E)-CIS-6,7-EPOXY-2-NONENAL, AND 1,1-DIALKOXY-6-NONEN-2-YNE COMPOUND
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, (2020/02/27)
The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound. There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): Y-Z-CR1═CR2—(CH2)2—C≡CH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): Y-Z-CR1═CR2—(CH2)2-X1 (1) and (ii) an alkyne compound of the following formula (2): X2=C≡C—Si(R3)(R4)(R5) (2) to a coupling reaction to form a silane compound of the following formula (3): Y-Z-CR1═CR2—(CH2)2—C≡C—Si(R3)(R4)(R5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).
Process for preparing (2e,6z)-2,6-nonadienal and a process for preparing (2e)-cis-6,7-epoxy-2-nonenal
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Paragraph 0119-0122; 0128-0131, (2019/12/25)
The object of the invention is to provide convenient and efficient processes for preparing (2E,6Z)-2,6-nonadienal and (2E)-6,7-epoxy-2-nonenal with a reduced number of steps. The present invention provides a process for preparing (2E,6Z)-2,6-nonadienal, comprising at least steps of subjecting a (6,6-dialkoxy-4-hexenylidene)triarylphosphorane compound of the general formula: Ar3P=CH(CH2)2CH=CHCH(OR)(OR) to a Witting reaction with propanal to form a 1,1-dialkoxy-(6Z)-2,6-nonadiene compound of the general formula (6); and subjecting the 1,1-dialkoxy-(6Z)-2,6-nonadiene compound to hydrolysisto form (2E,6Z)-2,6-nonadienal. Also provided is a process for preparing (2E)-cis-6,7-epoxy-2-nonenal of the formula (8), comprising a step of subjecting (2E,6Z)-2,6-nonadienal thus obtained to epoxidation to form (2E)-cis-6,7-epoxy-2-nonenal.
An Isotopic Study (2H and 18O) of the Enzymatic Conversion of Linoleic Acid into Colneleic Acid with Carbon Chain Fracture: the Origin of Shorter Chain Aldehydes
Crombie, Leslie,Morgan, David O.,Smith, Elisabeth H.
, p. 567 - 575 (2007/10/02)
Contrary to earlier reports, the divinyl 9-ether oxygen of colneleic acid is shown by experiment with 18O2 to originate from oxygen, not water.Using -9(S)-hydroperoxyoctadeca-10(E),12(Z)-dienoic acid, made enzymatically from synthetic linoleic acid, it is found that the distribution of deuterium as determined by NMR and mass spectrometry in the fractured carbon chain of colneic acid formed by potato enzyme, is consistent with the intervention of an epoxy carbonium ion intermediate.Though divinyl acids such as colneleic and colnelenic acid give the expected shorter chain aldehydes on treatment with aqueous acid, it is likely that the latter are formed in most plants by trapping of a monovinyl oxonium ion rather than by rehydration of colneleic and colnelenic acid.
