34683-71-1Relevant articles and documents
Evaluation of the key aroma compounds in beef and pork vegetable gravies a la chef by stable isotope dilution assays and aroma recombination experiments
Christlbauer, Monika,Schieberle, Peter
, p. 13122 - 13130 (2011)
Although the aroma compounds of meat processed as such have been studied previously, data on complete homemade dishes containing beef and pork meat were scarcely studied. Recently, 38 odor-active compounds were characterized in beef and pork vegetable gravies using GC-olfactometry. In the present investigation, the most odor-active compounds were quantitated in a freshly prepared stewed beef vegetable gravy (BVG) as well as a stewed pork vegetable gravy (PVG) by means of stable isotope dilution assays. Calculation of odor activity values (OAVs; ratio of concentration to odor threshold) revealed 3-mercapto-2- methylpentan-1-ol, (E,E)-2,4-decadienal, (E,Z)-2,6-nonadienal, (E)-2-decenal, (E)-2-undecanal, and 3-hydroxy-4,5-dimethyl-2(5H)-furanone as the most potent odorants in both gravies. However, significantly different OAVs were found for 12-methyltridecanal, which was much higher in the BVG, whereas (E,Z)-2,4-decadienal showed a clearly higher OAV in the PVG. Aroma recombination experiments performed on the basis of the actual concentrations of the odorants in both gravies revealed a good similarity of the aromas of both model mixtures containing all odorants with OAVs > 1 with those of the original gravies.
Enantioselective Synthesis and Antifungal Activity of C18 Polyacetylenes
Ding, Shengli,Feng, Jiayang,Li, Changkai,Li, Honglian,Li, Qing X.,Liu, Jia,Lu, Shichao,Na, Risong,Pei, Yiming,Wang, Wenliang,Zhang, Meng
, p. 2116 - 2123 (2020)
Fungal pathogens cause serious crop diseases and decrease crop yields and quality. Polyacetylene alcohols are plant secondary metabolites and bioactive against various pathogenic fungi. They are, however, difficult to synthesize. In the present study, an efficient and highly enantioselective method (>98% ee) was established and employed to achieve the synthesis of the natural C18 polyacetylenes (S,E)-octadeca-1,9-dien-4,6-diyn-3-ol 1, (3R,10R,E)-octadeca-1,8-dien-4,6-diyne-3,10-diol 2, and their analogs. The title compounds were structurally characterized and biologically evaluated for fungicidal activities. The compounds exhibited high potencies against eight pathogenic fungal species tested, such as Colletotrichum gloeosporioiles, Bipolaris sorokiniana, Fusarium graminearum, and Fusarium pseudograminearum, with half-maximum effective concentrations ranging from 8 to 425 μg/mL, being similar to those of the fungicide thiophanate-methyl (3-408 μg/mL). These compounds are potential natural fungicides and fungicide lead candidates for further structural and property improvements.
Catalytic asymmetric synthesis of Japonilure and its enantiomer
Xu, Hao,Li, Shuo-Ning,Yang, Yan-Qing,Zhou, Yun,Yang, Qian-Zhen,Bian, Qing-Hua,Zhong, Jiang-Chun,Wang, Min
, p. 1372 - 1375 (2015)
A mild, concise, and highly enantioselective (93% ee) synthesis of Japonilure and its enantiomer, Anomala osakana pheromone, is described. The key steps involve the asymmetric addition of methyl propionate to undec-2-ynal with a Zn-ProPhenol catalyst and the selective and partial reduction of the diynol ester to the cis-enol ester with Brown's P2-Ni catalyst, providing the first synthesis of the enol ester via semi-hydrogenating diynol ester.
Enantioselective synthesis method of chiral (6Z, 9Z)-3, 4-epoxy octadecadiene
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Paragraph 0048-0050; 0063-0065; 0078-0080, (2021/04/03)
The invention relates to the technical field of tea geometrid prevention and treatment, in particular to an enantioselective synthesis method of chiral (6Z, 9Z)-3, 4-epoxy octadecadiene. When the intermediate (2Z, 5Z)-octadiene-1-alcohol is used as a raw
Regioselective Iron-Catalysed Cross-Coupling Reaction of Aryl Propargylic Bromides and Aryl Grignard Reagents
Manjón-Mata, Inés,Quirós, M. Teresa,Bu?uel, Elena,Cárdenas, Diego J.
supporting information, p. 146 - 151 (2019/12/11)
An iron-catalysed Kumada-type cross-coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. The process is stereoespecific, occurs with configuration inversion and no carbon-based radicals seem to be involved in the mechanism. (Figure presented.).
Synthesis method of (3Z,6Z)-9,10-epoxy-octadecadiene
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Paragraph 0036; 0037-0039, (2019/02/26)
The invention discloses a synthesis method of (3Z,6Z)-9,10-epoxy-octadecadiene which is one of tea geometrid sex pheromone components. The synthesis method comprises the following steps: coupling propynyl alcohol with bromooctane to produce undec-2-yn-1-ol, and catalytically hydrogenating the undec-2-yn-1-ol to obtain cis-undec-2-en-1-ol; performing a reaction on the cis-undec-2-en-1-ol and m-chloroperoxybenzoic acid to obtain undec-2,3-epoxy-1-ol; sulfonylating hydroxyl groups of the undec-2,3-epoxy-1-ol by p-methylsufonyl chloride to obtain p-methylsulfonyl ester; performing ring opening onan epoxidized compound under the conditions of tri-tert-butylphosphine and chlorosuccinimide to obtain 3-chloro-2-hydroxyundecyl methanesulfonate, and then performing ring closure under an alkali condition to obtain 3-chloro-1,2-epoxyundecane; then, performing ring opening under the conditions of n-butyl lithium and boron trifluorideetherate, and performing ring closure under the condition of potassium carbonate to obtain 2-octyl-3-(prop-2-yn-1-yl)oxirane; then, obtaining 2-(octane-2,5-diyn-1-yl)-3-octyloxirane under the condition of an iodo coupling reagent; and finally, performing hydrogenation catalysis to obtain a final product. The synthesis method is relatively low in cost, and is suitable for scale preparation.
Stereoselective synthesis of C3–C17 and C18–C34 subunits of bullatanocin utilizing α-chloro sulfide intermediates
Chowhan, L. Raju,Raghavan, Sadagopan
supporting information, (2019/09/17)
A convergent synthesis of bullatanocin is envisaged by the union of C18–C34, C3–C17 and the butenolide subunits. The synthesis of the C3–C17 and C18–C34 subunits is disclosed that takes advantage of the chirality of tartaric acid for 1,2-asymmetric induct
Direct Access to Allenylphosphine Oxides via a Metal Free Coupling of Propargylic Substrates with P(O)H Compounds
Yang, Chun-Hua,Fan, Huihui,Li, Huimin,Hou, Shenyin,Sun, Xiangkun,Luo, Donghao,Zhang, Yinchao,Yang, Zhantao,Chang, Junbiao
supporting information, p. 9438 - 9441 (2019/11/20)
A direct and convenient approach for the coupling of propargylic substrates with diphenylphosphine oxide in the presence of Tf2O and 2,6-lutidine has been developed. The method provides a general approach for the construction of attractive allenylphosphoryl skeletons with high atom and step economy under metal free conditions.
Synthetic method of highly-activity chiral acetylenic alcohol (S,E)-1,9-diene-4,6-diacetyl-3-octadecyl alcohol
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Paragraph 0015; 0025-0027, (2018/09/13)
The invention discloses a synthetic method of highly-activity chiral acetylenic alcohol (S,E)-1,9-diene-4,6-diacetyl-3-octadecyl alcohol. The synthetic method disclosed by the invention comprises thefollowing steps: bromooctane is taken as a starting raw material and is reacted in a reasonable proportion to synthesize required alkynol; and the efficient synthesis of active molecule (S,E)-1,9-diene-4,6-diyne-3-octadecanol is realized through reduction, bromination, coupling reactions, desilication and docking with a chiral molecule. According to the method, the yield in the reaction process ishigh, a synthetic route is simple, the raw material is simple and easy to obtain, the synthetic cost is low, reaction conditions are mild, the separation and purification operations are simple, and ahigh-purity target compound can be directly obtained; a chiral center is introduced in the last step, so that the possibility of racemization of the substance in the reaction is avoided; and in addition, the synthesized active molecule (S,E)-1,9-diene-4,6-diyne-3-octadecanol has a wide application prospect.
Iron-Catalyzed Coupling of Propargyl Bromides and Alkyl Grignard Reagents
Domingo-Legarda, Pablo,Soler-Yanes, Rita,Quirós-López, M. Teresa,Bu?uel, Elena,Cárdenas, Diego J.
supporting information, p. 4900 - 4904 (2018/09/10)
An iron-catalyzed Kumada-type cross-coupling reaction of propargyl halides with alkylmagnesium reagents is described. The reaction is fast, takes place in smooth conditions, tolerates several functional groups that would be able to react with the Grignard reagent, and may afford either allene or propargyl coupling derivatives. Factors involved in the observed regioselectivity have been studied.
