柏木烷-8,9-二醇的合成及结构鉴定

doi:10.3969/j.issn.0253-2417.2014.01.014

Abstract

Abstract: Cedrane-8,9-diol(1H-3a, 11-Methanoazulen-8,9-diol, octahydro-2,6,6,8-tetramethyl)was synthesized from cedrene by peroxidation and hydration reactions in one pot, and the total yield was 52.5 %. Then the white needle crystal was produced by the process of settlement, vacuum distillation, crystallization and recrystallization. The GC content of cedrane-8,9-diol in the crystal was 99.3 %. The relative molecular weight and the molecular formula were determined by method of element analysis and mass spectrum (MS). The main peaks of Infrared spectrum (IR) showed that, there was no carbonyl group in the molecular structure of cedrane-8,9-diol, but there was two adjacent hydroxyls in it. The main high m/z ion peaks and low m/z ion peaks produced from the title compound by MS could be reasonably interpreted according to the raw materials and synthesis reaction mechanism. The MS detection results showed that the title compound has the same carbon skeleton with cedrene. The protons in the compound were exactly attached by ¹H NMR spectrum, and the molecule's structure was determined.

Key words: cedrene, cedrane-8,9-diol, synthesis, molecular structure

CLC Number:

TQ35
O621.15

ZHENG De-yong. Synthesis and Identification of Cedrane-8,9-diol[J]. Chemistry and Industry of Forest Products, 2014, 34(1): 86-90.

References

[1] 刘树文.合成香料技术手册[M].2版.北京:中国轻工业出版社, 2009.
[2] BHATIA S P, MCGINTY D, LETIZIA C S, et al.Fragrance material review on cedrol[J].Food and Chemical Toxicology, 2008, 46(11):S100-S102.
[3] 陈煜强, 刘幼军.香料产品开发与应用[M].上海:上海科学技术出版社, 1994.
[4] 陆熙娴, 王德隆.杉木精油化学成分的研究[J].林业科学, 1986, 22(3):323-328.
[5] HUANG Luo-hua, QIN Te-fu, OHIRA T.Studies on preparations and analysis of essential oil from Chinese fir[J].Journal of Forestry Research, 2004, 15(1):80-82.
[6] 叶舟, 林文雄, 陈伟, 等.杉木心材精油抑菌活性及其化学成分研究[J].应用生态学报, 2005, 16(12):2394-2398.
[7] 陆熙娴, 王德隆, 周明.杉木浸提物对木材天然耐腐、抗蚁性的影响[J].林业科学, 1987, 23(4):456-462.
[8] 陆熙娴, 周勤, 程政红.杉木阴沉木精油化学组成的研究[J].林产化学与工业, 1999, 19(2):67-72.
[9] 黄明泉, 田红玉, 刘玉平, 等.吉安杉木碎屑精油的化学成分分析研究[J].北京工商大学学报:自然科学版, 2008, 26(4):1-4.
[10] 程健, 曾韬, 杨彦春.杉木根干馏油提取杉木精油及化学成分分析[J].林产化学与工业, 2007, 27(S1):65-68.
[11] 傅星星, 郑德勇.浅谈杉木精油的开发前景[J].福建林业科技, 2008, 35(4):267-269.
[12] 陆洪都, 培根.过磷酸(SPA)可用作柏木烯乙酰化作用的催化剂[J].香料香精化妆品, 2003 (3):1-2, 13.
[13] 黄克瀛, 王美其, 张可君.用柏木油合成柏木酮的研究[J].林产化工通讯, 1996, 30(2):10-11.
[14] 刘名治, 万邵琥.合成香料乙酰基柏木烯的研究[J].南昌大学学报:工科版, 1986, 8(3):88-94.
[15] 续艳, 刘六军, 何亮, 等.罗汉柏木烯异构化反应工艺[J].东北林业大学学报, 2013, 41(6):124-126.
[16] 孙震, 赵振东, 李冬梅, 等.高纯度α-柏木烯的制备研究[J].林产化工通讯, 2002, 36(2):10-12.
[17] SARBANI D, ASHUTOSH P, DEBABRATA M.A stereocontrolled total synthesis of (±)-Δ2-cedrene[J].Tetrahedron Letters, 1996, 37(25):4421-4422.
[18] 宁永成.有机波谱学谱图解析[M].北京:科学出版社, 2010.
[19] PRETSCH E, BUHLMANN P, AFFOLTER C.波谱数据表——有机化合物的结构解析[M].上海:华东理工大学出版社, 2002.

Synthesis and Identification of Cedrane-8,9-diol

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