异长叶烷酮与水合肼的合成反应

doi:10.3969/j.issn.0253-2417.2016.02.019

Abstract

Abstract: Isolongifolane ketone Schiff base was synthesized with isolongifolane ketone and hydrazine as raw materials. The effects of different conditions on the reaction were studied by single factor and orthogonal experiments with the yield of the isolongifolane ketone Schiff base as the investigation index. The results showed that the optimized technological parameters were the catalyst dosage 0.6% (use the volume of all the material as the reference), ethanol as the solvent, reaction time 24 h, reaction temperature 78 ℃ and n(isolongifolane ketone):n(hydrazine) 1:5. Under these conditions, the yield of the product was 87.84%, and its chemical structure was analyzed by GC-MS,FT-IR and ¹H NMR spectra. They proved that the isolongifolane ketone Schiff base was synthesized.

Key words: isolongifolane ketone, hydrazine, Schiff base, turpentine

CLC Number:

TQ35

WANG Peng-na, XU Xu, CAI Tao, HUANG Jian-feng, WANG Shi-fa. Synthesis of Isolongifolane Ketone and Hydrazine[J]. Chemistry and Industry of Forest Products, 2016, 36(2): 129-133.

References

[1] 赵振东,刘先章.松节油的精细化学利用(Ⅱ)——松节油合成日化香料(上)[J].林产化工通讯,2001,35(2):41-46. ZHAO Zhen-dong,LIU Xian-zhang.Fine chemical utilization of turpentine oil (Ⅱ)——Perfumes derived from turpentine oil(a)[J].Journal of Chemical Industry of Forest Products,2001,35(2):41-46.
[2] 蒋凤池,王甡,李希成.异长叶烷酮的制备和立体化学[J].林产化学与工业,1988,8(2):28-33. JIANG Feng-chi,WANG Shen,LI Xi-cheng.Control oxidation for isolongfolene[J].Chemistry and Industry of Forest Products,1988,8(2):28-33.
[3] 高德华,向凤仙.长叶烯异构成异长叶烯的工艺研究[J].林化科技通讯,1983,17(2):41-44. GAO De-hua,XIANG Feng-xian.The study on isomerization of the isolongifolene with longifolene[J].Forest Science and Technology,1983,17(2):41-44.
[4] 蒋凤池,李希成.制备异长叶烷酮的改进方法[J].江西师范大学学报:自然科学版,1988(2):47-49. JIANG Feng-chi,LI Xi-cheng.The improved process for the synthesis of isolongifolane katone[J].Journal of Jiangxi Normal University:Natural Sciences Edition,1988(2):47-49.
[5] 汪春山,甘万开,刘汉兰.长叶烯水合反应的研究[J].武汉化工学院学报,1990,12(1):2-5. WANG Chun-shan,GAN Wan-kai,LIU Han-lan.The research of hydrous reaction of longifolene[J].Journal of Wuhan Institute of Technology,1990,12(1):2-5.
[6] WANG Shi-fa,ZHANG Ai-jun.Facile and efficient synthesis of isolongifolenone[J].Organic Preparations & Procedures International the New Journal for Organic Synthesis,2008,40(4):405-410.
[7] 陈慧宗,徐景士,周国斌,等.木香型香料异长叶烯基醇的合成[J].江西师范大学学报:自然科学版,1999,23(4):77-80. CHEN Hui-zong,XU Jing-shi,ZHOU Guo-bin,et al.The synthesis of isolongifolenyl alcohols perfumery with wood odour[J].Journal of Jiangxi Normal University:Natural Sciences Edition,1999,23(4):77-80.
[8] 陈慧宗,蒋凤池,刘艳清.2-羟甲基异长叶环烷和2-羟甲基异长叶烯的合成及结构表征[J].化学世界,1997(12):641-644. CHEN Hui-zong,JIANG Feng-chi,LIU Yan-qing.Synthensis and characterization of 2-hydroxymethyl isolongifolic cycloalkanes and 2-hydroxymethyl isolongifolene[J].Chemical World,1997(12):641-644.
[9] JAIN A K,VAIDYA A,RAVICHANDRAN V,et al.Recent developments and biological activities of thiazolidinone derivatives:A review[J].Bioorganic & Medicinal Chemistry,2012,20(11):3378-3395.
[10] KHAN S A,YUSUF M.Synthesis and biological evaluation of some thiazolidinone derivatives of steroid as antibacterial agents[J].European Journal of Medicinal Chemistry,2009,44(6):2597-2600.
[11] VERMA A,SARAF S K.4-Thiazolidinone:A biologically active scaffold[J].European Journal of Medicinal Chemistry,2008,43(5):897-905.
[12] VICINI P,GERONIKAKI A,INCERTI M,et al.2-Heteroarylimino-5-benzylidene-4-thiazolidinones analogues of 2-thiazolylimino-5-benzylidene-4-thiazolidinones with antimicrobial activity:Synthesis and structure-activity relationship[J].Bioorganic & Medicinal Chemistry,2008,16(7):3714-3724.
[13] FAN Xiang-qian,ZHANG Ling-xia,WANG Min,et al.Constructing carbon-nitride-based copolymers via Schiff base chemistry for visible-light photocatalytic hydrogen evolution[J].Applied Catalysis B:Environmental,2016,182:68-73.
[14] BENAROUS N,CHEROUANA A,AUBERT E,et al.Synthesis,characterization,crystal structure and DFT study of two new polymorphs of a Schiff base (E)-2-((2,6-dichlorobenzylidene) amino) benzonitrile[J].Journal of Molecular Structure,2016,1105:186-193.
[15] YUAN Cai-xia,LIU Xin-yu,WU Yan-bo,et al.A triazole Schiff base-based selective and sensitive fluorescent probe for Zn²⁺:A combined experimental and theoretical study[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2016,154:215-219.

Synthesis of Isolongifolane Ketone and Hydrazine

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	MA Yuan, DUAN Wengui, LIN Guishan, LIU Luzhi, HUANG Zhengsong, LEI Fuhou. Synthesis and Biological Activities of Perillaldehyde-based Schiff Base-(thio) urea Compounds [J]. Chemistry and Industry of Forest Products, 2017, 37(1): 54-62.
[2]	WANG Hong-qin, WANG Ya-ming, JIANG Li-hong, JIN Yan-qiong. Preparation and Catalytic Activity of[Rh(COD)Cl]₂ Catalyst for Turpentine Hydrogenation [J]. Chemistry and Industry of Forest Products, 2016, 36(6): 56-62.
[3]	YIN Bin, XU Wu-shuang, XIE Jing-cong, ZHANG Yu, LIU Qing-bo, LONG Jian-ying, FEI Bao-li. Comparation Study of DNA Binding Property with Dehydrobietic Benzimidazole Schiff Base and Hydrazone Derivatives [J]. Chemistry and Industry of Forest Products, 2016, 36(3): 81-87.
[4]	WANG Ping-ping, HUANG Zhi-xiang, GAO Wei-lin, ZHANG Jie, XU Wu-shuang, ZHANG Yu, LIU Qing-bo, LONG Jian-ying, FEI Bao-li. Binding Ability of N-(2-Methylene Pyridine) Dehydroabietylamine Schiff Base and Its Copper Complex with Bovine Serum Albumin [J]. Chemistry and Industry of Forest Products, 2016, 36(2): 15-22.
[5]	HAN Huan, JIANG Li-hong, WANG Ya-ming, HUANG Tai-yang, WANG Hong-qin. Preparation of Ni/TiO₂-Al₂O₃ Catalyst and Its Application inCatalyzing Hydrogenation of Turpentine [J]. Chemistry and Industry of Forest Products, 2016, 36(1): 92-98.
[6]	LIAO Sheng-liang, SHANG Shi-bin, SI Hong-yan, SHEN Ming-gui, RAO Xiao-ping, SONG Zhan-qian. Synthesis and Antibacterial Activities of Carboxylic Myrtanyl Esters [J]. Chemistry and Industry of Forest Products, 2015, 35(6): 33-38.
[7]	PENG Han, YANG Li-juan, XU Xu, WANG Shi-fa. Green Synthesis of Isolongifolenone [J]. Chemistry and Industry of Forest Products, 2015, 35(3): 97-103.
[8]	WANG Jing;ZHAO Zhen-dong;BI Liang-wu;LI Dong-mei;. Review on Isomerization of the Major Monoterpenes in Turpentine [J]. , 2013, 33(2): 144-150.
[9]	FEI Bao-li;LI Wen;ZHANG Dian;XIA Bing;LONG Jian-ying;LIU Qing-bo. DNA-Binding Studies of Dehydroabietylamine and Its Schiff Base Derivatives [J]. , 2012, 32(5): 1-6.
[10]	LU Rui-li;HU Feng-lin;XU Bin. Primary Studies on Free Radical Scavenging Activities of Extracts from 50 Kinds of Woods [J]. , 2011, 31(1): 91-94.
[11]	WEN Xue-ying;ZHOU Jia-hua;ZHAO Zi-niu. Location of Temperature-sensitive Plates in Turpentine Distillation Tower [J]. , 2010, 30(3): 57-60.
[12]	LIU Shi-wei;YU Shi-tao;LIU Fu-sheng;XIE Cong-xia;JI Kai-hui. Synthesis of Terpinyl Acetate Catalyzed by Acidic Functional Ionic Liquid Sulfonic Alkylimidazole Phosphate [J]. , 2007, 27(S1): 33-36.
[13]	BAI Li-juan;LEI Fu-hou;MO Li-jun;LUO Ying;HUANG Yong-zhong. Study on Oxidation of Styrene Catalyzed by Copper Complex of Disproportionated Rosin Amine Schiff Base [J]. , 2007, 27(S1): 99-104.
[14]	LI Lu;YU Shi-tao;LIU Fu-sheng;XIE Cong-xia. Hydration of α-Pinene Catalyzed by SO₄^2-/Zr-MCM-41 in Supercritical Carbon Dioxide [J]. , 2007, 27(S1): 94-98.
[15]	RAO Xiao-ping;SONG Zhan-qian;GAO Hong . Synthesis and Antibacterial Activity of Fluorine-containing Schiff Bases Derived from Dehydroabietylamine [J]. , 2007, 27(2): 97-99.