欢迎访问《林产化学与工业》，
林产化学与工业

林产化学与工业 ›› 2016, Vol. 36 ›› Issue (5): 1-7.doi: 10.3969/j.issn.0253-2417.2016.05.001

• 研究报告 •    下一篇

3-(2'-羟基亚苄基)诺蒎酮的合成、表征及其酸碱指示性能研究

杨金来1,2, 张燕1, 芮坚1, 孙楠1, 徐徐1,3,5, 杨益琴4, 王石发1,3,5   

  1. 1. 南京林业大学 化学工程学院, 江苏 南京 210037;
    2. 国家林业局 竹子研究开发中心, 浙江 杭州 310012;
    3. 南京林业大学 江苏省林业资源高效加工利用协同创新中心, 江苏 南京 210037;
    4. 南京林业大学 轻工科学与工程学院, 江苏 南京 210037;
    5. 江苏省生物质绿色燃料与化学品重点实验室, 江苏 南京 210037
  • 收稿日期:2015-12-08 出版日期:2016-10-25 发布日期:2016-11-05
  • 通讯作者: 王石发,教授,博士生导师,主要从事手性合成研究;E-mail:wsfyyq@njfu.com.cn。 E-mail:wsfyyq@njfu.com.cn
  • 作者简介:杨金来(1981-),男,河北保定人,博士生,主要从事天然产物的有机合成
  • 基金资助:
    江苏省普通高校学术学位研究生科研创新项目（2014，KYZZ-0252）；国家自然科学基金资助项目（31470592）；江苏省生物质能源与材料重点实验室开放基金（JSBEM2014010）

Synthesis and Characterization of 3-(2'-Hydroxybenzylidene) Nopinone and Its Acid-base Indicator Performance

YANG Jin-lai1,2, ZHANG Yan1, RUI Jian1, SUN Nan1, XU Xu1,3,5, YANG Yi-qin4, WANG Shi-fa1,3,5   

  1. 1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;
    2. China National Bamboo Research Center, Hangzhou 310012, China;
    3. Jiangsu Co-innovation Center of Efficient Process and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China;
    4. College of Light Industry Science and Engineering, Nanjing Forestry University, Nanjing 210037, China;
    5. Jiangsu Key Lab. of Biomass-based Green Fuels and Chemicals, Nanjing 210037, China
  • Received:2015-12-08 Online:2016-10-25 Published:2016-11-05

PDF (PC)

577

摘要： 以β-蒎烯为原料，先经氧化反应合成诺蒎酮，诺蒎酮与水杨醛进一步经羟醛缩合反应合成了3-（2’-羟基亚苄基）诺蒎酮，通过单因素和正交试验优化了缩合反应的工艺条件。结果表明：缩合反应的优化工艺条件为：诺蒎酮1.43 g，以30 mL叔丁醇为溶剂，2.5 g叔丁醇钾为催化剂，n（诺蒎酮）：n（水杨醛）为1.0：1.2，回流反应2 h，产物得率为79.46%。采用MS、IR、NMR、X射线单晶衍射等对3-（2’-羟基亚苄基）诺蒎酮的结构进行了表征，确认了化合物的结构，该化合物的晶体属单斜晶系，P212121空间群。对3-（2’-羟基亚苄基）诺蒎酮的酸碱指示性能进行了研究，结果表明：该化合物滴定0.257 4 mol/L盐酸标准溶液时，指示颜色为橘黄色，测定的盐酸浓度为0.259 6 mol/L，RSD为0.089%，滴定的灵敏度高、偏差小，效果优于酚酞指示剂。

关键词: 诺蒎酮, 羟醛缩合, 3-(2'-羟基亚苄基)诺蒎酮, 酸碱指示剂

Abstract: Nopinone was first synthesized by oxidation reaction of β-pinene. 3-(2'-Hydroxybenzylidene)nopinone was further synthesized by aldol condensation reaction of nopinone and salicylaldehyde and the process conditions were optimized by single factor and orthogonal experiment. The optimal condensation reaction conditions were determined as follows:1.43 g nopinone, tert-butyl alcohol (30 mL) as the solvent, potassium tert-butoxide (2.5 g) as the catalyst, the molar ratio of nopinone and salicylaldehyde 1:1.2 and the reflux reaction time 2 h. Under these condition, the yield of 3-(2'-hydroxybenzylidene)nopinone was 79.46%. The structure of 3-(2'-hydroxybenzylidene)nopinone was characterized and confirmed by MS, IR, NMR, and X-ray diffraction, and the crystal was in monoclinic system with P212121 space group. The acid-base indicator performance of 3-(2'-hydroxybenzylidene)nopinone was investigated. The results showed that the final color was orange and the measured concentration of hydrochloric acid was 0.259 6 mol/L with the RSD of 0.089%. When this compound was used to titrate hydrochloric acid standard solution (0.257 4 mol/L). As an acid-base indicator, 3-(2'-hydroxybenzylidene)nopinone was better than phenolphthanlein because of its high sensitivity and small deviation.

Key words: nopinone, aldol condensation, 3-(2'-hydroxybenzylidene)nopinone, acid-base indicator

中图分类号: 

版权所有 © 中国林业科学研究院林产化学工业研究所　苏ICP备08107184号-3