CAS: 710-04-3; 6-Hexyltetrahydro-2H-Pyran-2-One

该化合物是源自非decanoic酸的循环酯,其特点是独特的内酯环结构.该化合物因其作为香味和香味中间体的作用而引人注目,有助于乳油,水果和椰子般芳香素.其稳定性和低挥发性使其适合香水和食品调味.三角酯-Lactone配置增强了其与水分恐惧基体的兼容性,确保了配方的一贯性.此外,高纯度和受控制的合成可精确用于精细化学应用.在工业和研究环境中,Undecanoic delta-Lactone因其多功能和可靠性而备受重视.

结构式图片

相似化合物

705-86-2 713-95-1 7370-92-5

欧盟法规

REACH注册ECHA物质C&L通报REACH预注册

上下游产品

CAS号36971-14-9 1-hexylbut-3-en-1-ol | CAS号79-10-7 丙烯酸 | CAS号13074-65-2 2-己基环戊酮 | CAS号401515-97-7 2-pyridylmethyl... | CAS号13686-98-1 undecane-1,5-diol | CAS号4291-99-0 1-hexylcyclopentene | CAS号36633-49-5 1-hexylcyclopen... | CAS号16424-28-5 5-oxoundecanoic acid | CAS号918343-84-7 ethyl 4-hydroxy...

合成工艺路线路线简述

  • 合成目标产物 Undecanolactone 主要起始原料 Gamma-Decalactone
  • (文献来源)合成步骤主要原料 Gamma-Decalactone
2-己基环戊酮置于d-葡萄糖体系中,化学反应 1.0H,反应生成 丁位十一内酯
参考文献:通过对映选择性还原,氧化和水解进行级联生物转化:由2-亚烷基亚环戊酮制备(R)-δ-内酯
标题:通过对映选择性还原,氧化和水解进行级联生物转化:由2-亚烷基亚环戊酮制备(R)-δ-内酯
摘要:作为涉及绿色和可持续的合成对映纯δ-内酯的工具,首次涉及级联生物转化涉及c═c双键的对映选择性还原,Baeyer-Villiger氧化和内酯水解.不动杆菌属一锅级联生物转化.rs1含有新颖的对映选择性还原酶和对映体选择性内酯水解酶和大肠杆菌共表达的环己酮单加氧酶和葡糖脱氢酶,转换容易获得的2-Alkylidenecyclopentanones 1-2成相应的有价值的香精香料([r)-δ-内酯5-6在高ee中.一锅法合成优于报道的两步法制备.该概念对于开发其他包含c═c双键的底物的氧化还原级联反应很有用.
DOI:10.1021/cs400101V

海关参考信息

专利信息


专利号:US-4451392-A
优先权日:1982-09-30
标题:Synthesis of triconjugated dienones and novel intermediates used in said process
发明人:EVERS WILLIAM J; STORK GILBERT; MOOKHERJEE BARJA D; HEINSOHN JR HOWARD H
权利人:INT FLAVORS & FRAGRANCES INC
摘要:Described is a process for preparing triconjugated dienones defined according to the structure: wherein R1 represents C1-C8 alkyl, phenyl or phenyl methyl and wherein R2 represents hydrogen or C1-C5 lower alkyl; and wherein the wavy lines are indicative of a 'cis' or a 'trans' juxtaposition of the R2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: wherein R3 represents C1-C5 alkyl in the presence of an aluminum chloride catalyst and a methylene dichloride solvent in order to form the novel intermediate genus defined according to the structure: then dehydrohalogenating the compound defined according to the structure: using an alkali metal carbonate and a dimethylformamide solvent in order to form the novel compound genus having the structure: wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and then dehydroacyloxylating the compound having the structure: in order to form the compound having the structure: the dehydroacyloxylation step taking place in the presence of an alkali metal carbonate and dimethylformamide solvent.

专利号:US-4560791-A
优先权日:1982-09-30
标题:Synthesis of triconjugated dienones and intermediates used in said process
发明人:EVERS WILLIAM J; STORK GILBERT; MOOKHERJEE BRAJA D; HEINSOHN JR HOWARD H
权利人:INT FLAVORS & FRAGRANCES INC
摘要:Described is a process for preparing triconjugated dienones defined according to the structure: wherein R1 represents C1-C8 alkyl, phenyl or phenyl methyl and wherein R2 represents hydrogen or C1-C5 lower alkyl; and wherein the wavy lines are indicative of a 'cis' or a 'trans' juxtaposition of the R2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: wherein R3 represents C1-C5 alkyl in the presence of an aluminum chloride catalyst and a methylene dichloride solvent in order to form the novel intermediate genus defined according to the structure: then dehydrohalogenating the compound defined according to the structure: using an alkali metal carbonate and a dimethylformamide solvent in order to form the novel compound genus having the structure: wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and then dehydroacyloxylating the compound having the structure: in order to form the compound having the structure: the dehydroacyloxylation step taking place in the presence of an akali metal carbonate and dimethylformamide solvent.

专利号:US-4467820-A
优先权日:1982-09-30
标题 :Synthesis of triconjugated dienones and novel intermediates used in said process
发明人:EVERS WILLIAM J; STORK GILBERT; MOOKHERJEE BRAJA D; HEINSOHN JR HOWARD H
权利人:INT FLAVORS & FRAGRANCES INC
摘要:Described is a process for preparing triconjugated dienones defined according to the structure: wherein R1 represents C1-C8 alkyl, phenyl or phenyl methyl and wherein R2 represents hydrogen or C1-C5 lower alkyl; and wherein the wavy lines are indicative of a 'Cis' or a 'trans' juxtaposition of the R2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: with a substituted or unsubstituted prenyl ester having the structure: wherein R3 represents C1-C5 alkyl in the presence of an aluminum chloride catalyst and a methylene dichloride solvent in order to form the novel intermediate genus defined according to the structure: then dehydrohalogenating the compound defined according to the structure: using an alkali metal carbonate and a dimethylformamide solvent in order to form the novel compound genus having the structure: wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and then dehydroacyloxylating the compound having the structure: in order to form the compound having the structure: the dehydroacyloxylation step taking place in the presence of an alkali metal carbonate and dimethylformamide solvent.

专利号:US-5103047-A
优先权日:1990-05-01
标题:Process for preparation of 4- and 5-ketocarboxylic acids
发明人:VISO MIGUEL; REID JACK R
权利人:LORILLARD TOBACCO CO
摘要:This invention is a novel synthesis of 4-and 5-ketocarboxylic acids which includes the reaction of the appropriate delta- or gamma-lactone with a chromosulfuric acid solution and separating the 4- or 5-ketocarboxylic acid product from the reduced solution.

专利号:US-4560802-A
优先权日:1982-09-30
标 题:Synthesis of triconjugated dienones and novel intermediates used in said process
发明人:EVERS WILLIAM J; STORK GILBERT; MOOKHERJEE BRAJA D; HEINSOHN JR HOWARD H
权利人:INT FLAVORS & FRAGRANCES INC
摘要:Described is a process for preparing triconjugated dienones defined according to the structure: wherein R1 represents C1-C8 alkyl, phenyl or phenyl methyl and wherein R2 represents hydrogen or C1-C5 lower alkyl; and wherein the wavy lines are indicative of a 'cis' or a 'trans' juxtaposition of the R2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: wherein R3 represents C1-C5 alkyl in the presence of an aluminum chloride catalyst and a methylene dichloride solvent in order to form the novel intermediate genus defined according to the structure: then dehydrohalogenating the compound defined according to the structure: using an alkali metal carbonate and a dimethylformamide solvent in order to form the novel compound genus having the structure: wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and then dehydrocyloxylating the compound having the structure: in order to form the compound having the structure: the dehydroacyloxylation step taking place in the presence of an alkali metal carbonate and dimethylformamide solvent.

专利号:US-4623749-A
优先权日:1982-09-30
标题:Synthesis of triconjugated dienones and novel intermediates used in said process
发明人:EVERS WILLIAM J; STORK GILBERT; MOOKHERJEE BRAJA D; HEINSOHN JR HOWARD H
权利人:INT FLAVORS & FRAGRANCES INC
摘要:Described is a process for preparing triconjugated dienones defined according to the structure: wherein R1 represents C1-C8 alkyl, phenyl or phenyl methyl and wherein R2 represents hydrogen or C1-C5 lower alkyl; and wherein the wavy lines are indicative of a 'cis' or a 'trans' juxtaposition of the R2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide with a substituted or unsubstituted prenyl ester having the structure: wherein R3 represents C1-C5 alkyl in the presence of an aluminum chloride catalyst and a methylene dichloride solvent in order to form a halogen-ester intermediate defined according to the structure: then dehydrohalogenating said halogen-ester intermediate using an alkali metal carbonate and a dimethylformamide solvent in order to form a ketoester having the structure: wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and then dehydroacyloxylating the ketoester in the presence of an alkali metal carbonate and dimethylformamide solvent in order to form the triconjugated dienone.
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主要参考文献

[参考文献]: S Billecke, Et Al. Human Serum Paraoxonase (Pon1) Isozymes Q And R Hydrolyze Lactones And Cyclic Carbonate Esters. Drug Metab Dispos. 2000 Nov;28(11):1335-42.

合成参考文献


参考文献:10.1007/978-1-61779-136-9_2
摘要:Chu X, Zhang F, Nie X, Wang W, Feng F. China's food safety regulation and mass spectrometry. Methods Mol Biol. 2011;747():21–51. doi: 10.1007/978-1-61779-136-9_2.
参考文献:10.1186/1756-0500-7-333
摘要:Bzdrenga J, Hiblot J, Gotthard G, Champion C, Elias M, Chabriere E. Sac Pox from the thermoacidophilic crenarchaeon Sulfolobus acidocaldarius is a proficient lactonase. BMC Research Notes. 2014 Jun 03;7(1):333. doi: 10.1186/1756-0500-7-333.
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