α-环香叶酸的合成工艺研究
PDF下载 (401)胡艳华,江峰,赵洋洋,张剑锋*.α-环香叶酸的合成工艺研究[J].宁波大学学报(理工版),2016,29(1):73-76.DOI:
HU Yan-hua,JIANG Feng,ZHAO Yang-yang,ZHANG Jian-feng*.Synthesis and Process of the -cyclogeranic Acid: Research[J].Journal of Ningbo University(Natural Science & Engineering Edition),2016,29(1):73-76.DOI:
| Title: | Synthesis and Process of the -cyclogeranic Acid: Research |
| 作者: | 胡艳华, 江峰, 赵洋洋, 张剑锋* |
| Author(s): | HU Yan-hua, JIANG Feng, ZHAO Yang-yang, ZHANG Jian-feng* |
| 关键词: | α-环香叶酸; 柠檬醛; 氧化; 关环 |
| Keywords: | -cyclogeranic acid; citral; oxidation; cyclization |
| 分类号: | O622.5 |
| 文献标识码: | A |
| 摘要: | α-环香叶酸是合成大马酮类香料的关键中间体, 比较了现有的几种α-环香叶酸的合成方法, 选择和确认了一条以柠檬醛为原料, 经氧化关环得到α-环香叶酸的合成工艺, 其合成的α-环香叶酸纯度可达到96.6%, 总产率为65.3%. 该合成方法具有反应条件温和、总产率较高的优点, 适合工业化生产. |
| Abstract: | α-cyclogeranic acid is a key intermediate of the damascones. Based on comparison of several synthetic methods in the literatures, α-cyclogeranic acid is synthesized from citral through oxidation and cyclization. This synthetic method has advantages such as mild conditions and high yield, the yield of the α-cyclogeranic acid can be as high as 65.3%, and the purity of the product can reach as high as 96.6%. This method is found to be suitable for industrial production |
| 参考文献 /References: | [1].CHARLES F, HARVEY R. Synthetic applications of enantioselective protonation and case study for (s)-α- damascone[J]. Chemistry & Biodiversity, 2008, 5:942- 957. [2].李琼, 黄亚文, 卢星, . 由环香叶酸乙酯合成β-突厥酮[J]. 化学通报, 2011, 74:275-279. [3].KIM S, KIM E, SHIN D S, et al. Evaluation of morphogenic regulatory activity of farnesoic acid and its derivatives against candida albicans dimorphism[J]. Bioorganic & Medicinal Chemistry Letters, 2002, 12(6): 895-898. [4].DONG H B, JIANG J Z, WANG M A, et al. Total synthesis of 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide and 3,7- dimethyl-2, 6-octadien-1,6-olide[J]. Journal of Asian Natural Products Research, 2013, 15(8):880-884. [5].DALCANALE E, MONTANARI F. Selective oxidation of aldehydes to carboxylic acids with sodium chlorite- hydrogen peroxide[J]. Journal of Organic Chemistry, 1986, 51(4):567-569. [6].GANDOLFI R, FERRARA N, MOLINARI F. An easy and efficient method for the production of carboxylic acids and aldehydes by microbial oxidation of primary alcohols[J]. Tetrahedron Letters, 2001, 42(3):513-514. [7].ABARBRI M, PARRAIN J L, DUCH?NE A. Stereospecific synthesis of (Z) or (E)-3-methylalk-2- enoic acids[J]. Tetrahedron Letters, 1995, 36(14):2469- 2472. [8].DOMINGO L R, SALVADOR G, MARGARITA P, et al. Experimental and theoretical investigations for the tandem alkylation-isomerization reactions between unsaturated carboxylic acids and allyl halides[J]. Tetrahedron, 2003, 59(33):6233-6239. [9].ANDERSEN J F, WALDING J K, EVANS P H, et al. Substrate specificity for the epoxidation of terpenoids and active site topology of house fly cytochrome P450 6A1[J]. Chemical Research in Toxicology, 1997, 10(2):156-164. [10].WHEELER J W, AYORINDE F O, GREENE A, et al. citronellyl citronellate and citronellyl geranate in the european hornet, vespa crabro (hymenoptera: vespidae)[J]. Tetrahedron Letters, 1982, 23(20):2071-2072. [11].UROOS M, HAYES C J. Synthesis of the spirochroman core of dihypoestoxide and stereochemical proposal for the natural product[J]. Organic Letters, 2010, 12(22): 5294-5297. [12].K?DAS I, ?RVAI G, HORV?TH G. Improved synthesis of 7,7-dimethyl-1,4-dioxo-2,3,4,5,6,7-hexahydroinden-2- yl-acetic and propionic acid from citral[J]. Organic Preparations and Procedures International, 1998, 30(1): 79-86. [13].TIEMANN F. Ueber die verbindungen der cyclo-citral- reihe[J]. Chemische Berichte, 1900, 33(3):3703-3710. [14].GAN Y, LI A, PAN X, et al. Stereoselective synthesis of (-)-6,7-dehydroferruginyl methyl ether[J]. Tetrahedron: Asymmetry, 2000, 11:781-787. |
| 备注/Memo: | 收稿日期: 2014?11?17. 宁波大学学报(理工版)网址: http://journallg.nbu.edu.cn/ 基金项目: 宁波市自然科学基金(2012A610086), 宁波大学创新开放实验项目(cxxkf201415); 宁波大学研究生教育改革项目(JGZDI201302). 第一作者: 胡艳华(1991-), 女, 江西鄱阳人, 在读硕士研究生, 主要研究方向: 有机合成及催化. E-mail: huyanhua1124@126.com *通信作者: 张剑锋(1968-), 男, 湖南邵阳人, 博士/副教授, 主要研究方向: 合成化学. E-mail: zjf@nbu.edu.cn 宁波大学学报(理工版)网址:http://journallg.nbu.edu.cn/ |