6789-80-6Relevant articles and documents
The synthesis of 3,4-2H2-3Z-Hexenal and 6,6,62H3-3Z-Hexenal
Fielder,Rowan
, p. 465 - 470 (1995)
6,6,6-2H3-3Z-Hexenal (3b) has been prepared in 89% yield and in greater than 94% purity by the oxidation of 6,6,63H3-3Z-Hexen-1-of (2b) with the Dess/Martin periodinane (1) in fluorotrichloromethane (freon 11). Use of the freon solvent greatly improved the recovery of this volatile aldehyde. Similarly the oxidation of 3,4-2H2-3Z-hexen-1-of (5) yielded 3,4-2H2-3Z-hexenal (6) in a 92% isolated yield with a purity of greater than 99%. 3,4-2H2-3Z-Hexen-1-of (5) Was prepared in 87% by the catalytic deuterogenation of 3-hexyn-1-of (4) in an improved synthetic procedure,
Method for synthesizing geraniol from piperylene (by machine translation)
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Paragraph 0038-0041; 0044-0045, (2020/07/12)
The method comprises the following steps: reacting piperylene with carbon monoxide and hydrogen to prepare an intermediate cis -3 -hexene -1 - aldehyde; and preparing the geraniol through hydrogenation. The yield of the leaf alcohol is 81.56-92 .73percent, the yield of the cis -3 - hexenyl -1 - aldehyde is 80.69-88 .13percent, the yield of the leaf alcohol is -3 - 54.94-80 .35percent (calculated by pentadiene), the yield of the leaf alcohol is 99.2-99 .50percent.1 - percent, and the yield fluctuation range of the leaf alcohol is 10 within 55.53-80 .97percent percent of the yield of the leaf 0.4 alcohol in 98.36-99 .60percent percent. (by machine translation)
Structure-Odor Relationships of (Z)-3-Alken-1-ols, (Z)-3-Alkenals, and (Z)-3-Alkenoic Acids
Lorber, Katja,Zeh, Gina,Regler, Johanna,Buettner, Andrea
, p. 2334 - 2343 (2018/03/21)
(Z)-3-Unsaturated volatile acids, alcohols, and aldehydes are commonly found in foods and other natural sources, playing a vital role in the attractiveness of foods but also as compounds with chemocommunicative function in entomology. However, a systematic investigation of their smell properties, especially regarding humans, has not been carried out until today. To close this gap, the odor thresholds in air and odor qualities of homologous series of (Z)-3-alken-1-ols, (Z)-3-alkenals, and (Z)-3-alkenoic acids were determined by gas chromatography-olfactometry. It was found that the odor qualities in the series of the (Z)-3-alken-1-ols and (Z)-3-alkenals changed, with increasing chain length, from grassy, green to an overall fatty and citrus-like, soapy character. On the other hand, the odor qualities of the (Z)-3-alkenoic acids changed successively from cheesy, sweaty via plastic-like, to waxy in their homologous series. With regard to their odor potencies, the lowest thresholds in air were found for (Z)-3-hexenal, (Z)-3-octenoic acid, and (Z)-3-octenal.
Method for asymmetric synthesis of (R)-jasmine lactone
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Paragraph 0020-0022, (2017/08/31)
The invention discloses a method for asymmetric synthesis of (R)-jasmine lactone. The method comprises the steps: oxidating (Z)-3-hexen-1-ol 1, which serves as a starting raw material, with a DMP reagent, so as to obtain (Z)-3-hexenoic aldehyde 2; then, carrying out an asymmetric addition reaction with methyl alkyne-butyrate in the presence of a (R,R)-ProPhenol ligand and zinc methyl, so as to obtain (S,Z)-5-hydroxyl-7-decen-3-methyl acetylenate 3; reducing a triple bond into a single bond with NaBH4 in the presence of CuI, so as to produce (R,Z)-5-hydroxyl-7-methyl decenoate 4; and finally, carrying out treatment with para-toluenesulfonic acid, and carrying out ring closing, thereby obtaining the target product, i.e., (R)-jasmine lactone. According to the method, the synthesis route is simple and direct, the reaction conditions are mild, the total yield is 42%, and the optical purity of the product is 95%.
