7-芳亚甲基异长叶烷酮类化合物的合成及其
紫外吸收特征

doi:10.3969/j.issn.1000-2006.2016.02.015

国家林草科技领军期刊
中国精品科技期刊
中国高校百佳科技期刊
江苏省新闻出版政府奖期刊奖
RCCSE林学权威期刊（A+）
CSCD核心期刊
Scopus数据库收录期刊
中文核心期刊
SCD核心期刊

作者加群：102861116

微信公众号：南京林业大学学报

高级检索

南京林业大学学报（自然科学版） ›› 2016, Vol. 40 ›› Issue (02): 88-94.doi: 10.3969/j.issn.1000-2006.2016.02.015

7-芳亚甲基异长叶烷酮类化合物的合成及其紫外吸收特征

芮坚¹,徐徐^1,2,4,杨益琴³,黄建峰¹,王石发^1,3,4*

1.南京林业大学化学工程学院,江苏南京 210037;
2.江苏省生物质绿色燃料与化学品重点实验室, 江苏南京 210037;
3.南京林业大学轻工科学与工程学院,江苏南京 210037;
4.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

出版日期:2016-04-18 发布日期:2016-04-18
基金资助:
收稿日期:2015-04-24 修回日期:2015-11-15
基金项目:江苏省高校自然科学研究重大项目(14KJA220001); 国家自然科学基金项目(31170538,31470592); 江苏省生物质能源与材料重点实验室开放基金(JSBEM2014010)
第一作者:芮坚(nanlinruijian@sina.com)。*通信作者:王石发(wsfyyq@njfu.com.cn),教授。
引文格式:芮坚,徐徐,杨益琴,等. 7-芳亚甲基异长叶烷酮类化合物的合成及其紫外吸收特征[J]. 南京林业大学学报:自然科学版,2015,39(6):88-94.

Synthesis and ultraviolet absorption characteristics of 7-arylidene-isolongifolanene

RUI Jian¹,XU Xu^{1, 2, 4},YANG Yiqing³,HUANG Jianfeng¹,WANG Shifa^1,3,4*

1. College of Chemical Engineering, Nanjing Forestry University,Nanjing 210037,China;
2. Jiangsu Key Laboratory Biomass Green Fuels and Chemicals, Nanjing 210037,China;
3. College of Light Industry Science and Engineering, Nanjing Forestry Un

Online:2016-04-18 Published:2016-04-18

摘要/Abstract

摘要： 以异长叶烷酮为原料,采用叔丁醇钾为催化剂,分别与对溴苯甲醛、对氟苯甲醛、间硝基苯甲醛、2,4-二氯苯甲醛等进行缩合反应,合成了系列7-芳亚甲基异长叶烷酮类化合物a—j。采用¹H NMR、¹³C NMR、GC-MS和FT-IR等分析手段对合成所得7-芳亚甲基异长叶烷酮类化合物的结构进行了鉴定,并探索了化合物a—j的紫外吸收特性与光稳定性。结果表明:化合物a、b、c、d、j对中波紫外线(UVB)具有良好的吸收性能; 而化合物e、f、g、h和i对长波紫外线(UVA)和UVB均具有较好的吸收性能。化合物a—j的光稳定顺序为h>g>e>c>a>d>b>f>i>j,其紫外线吸收强度顺序为d>i>e>h>g>f>b>c>j>a。

Abstract: A series of 7-arylidene-isolongifolanone a—j were synthesized by condensation of isolongifolanone with aromatic aldehydes including 4-bromobenzaldehyde, 4-fluorobenzaldehyde, 3-nitrobenzaldehyde, 2,4-dichlorobenzaldehyde under catalyzation of potassium tert-butoxide. The structures of compounds a—j were identified by means of ¹H NMR, ¹³C NMR, GC-MS and FT-IR, and their ultraviolet absorption characteristics as well as light stabilities were also investigated. The results showed that compounds a, b, c, d and j exhibited good absorbency as the medium-wave ultraviolet(UVB)type absorbents,and compounds e, f, g, h and i had both functions as long-wave ultraviolet(UVA)and UVB absorbents. The light stability sequence of those compounds was h>g>e>c>a>d>b>f>i>j. The UV absorption intensity was d>i>e>h>g>f>b>c>j>a.

中图分类号:

TQ450

芮坚,徐徐,杨益琴,等. 7-芳亚甲基异长叶烷酮类化合物的合成及其紫外吸收特征[J]. 南京林业大学学报（自然科学版）, 2016, 40(02): 88-94.

RUI Jian,XU Xu^{1, 2, 4},YANG Yiqing,HUANG Jianfeng,WANG Shifa^1,3,4*. Synthesis and ultraviolet absorption characteristics of 7-arylidene-isolongifolanene[J].Journal of Nanjing Forestry University (Natural Science Edition), 2016, 40(02): 88-94.DOI: 10.3969/j.issn.1000-2006.2016.02.015.

参考文献

[1] 梁均, 苏宁, 郑洪艳, 等. 几种防晒剂及其复配物紫外吸收特征的研究[J]. 香料香精化妆品, 2014(3): 47-51. Liang J, Su N, Zheng H Y, et al. Study on the UV-Absorbing characteristic of UV filters and their mixtures[J]. Flavour Fragrance Cosmetics, 2014(3): 47-51.
[2] Dobashi Y, Yuyama T, Ohkatsu Y. Interaction of ultraviolet absorbers[J]. Polymer Degradation and Stability, 2007, 92(7): 1227-1233.
[3] Uehara F, Miwa S, Tome Y, et al. Imaging of UVB and UVC-induced DNA damage repair in cancer cells in Gelfoam histoculture and minimal cancer in mice[J]. Cancer Research, 2014, 74(19 S): 2403.
[4] Agar N S, Halliday G M, Barnetson R S C, et al. The basal layer in human squamous tumors harbors more UVA than UVB fingerprint mutations: a role for UVA in human skin carcinogenesis[J]. Proceedings of the National Academy of Sciences of the United States of America, 2004, 101(14): 4954-4959.
[5] Chatelaine E, Gabard B. Photochemistry, Photophysics and phototechnology-photostabilization of butyl methoxydibenzoylmethane(avobenzone)and ethylhexyl methoxycinnamate by bis-ethylhexyloxyphenol methoxyphenyl triazine[J]. Photochemistry and Photobiology, 2001, 74(3): 401-406.
[6] Vanquerp V, Rodriguez C, Coiffard C, et al.High-performance liquid chromatographic method for the comparison of the photostability of five sunscreen agents[J]. Journal of Chromatography A, 1999, 832(1): 273-277.
[7] Wlaschek M, Tantcheva-Poór I, Naderi L, et al. Solar UV irradiation and dermal photoaging[J]. Journal of Photochemistry and Photobiology B: Biology, 2001, 63(1): 41-51.
[8] Das B R. UV radiation protective clothing[J]. Open Textile Journal, 2010, 3: 14-21.
[9] Kuchel J M, Barnetson R S C, Zhuang L, et al. Tamarind inhibits solar-simulated ultraviolet radiation-induced suppression of recall responses in humans[J]. Letters in Drug Design & Discovery, 2005, 2(2): 165-171.
[10] Li D, Turi T G, Schuck A, et al. Rays and arrays: the transcriptional program in the response of human epidermal keratinocytes to UVB illumination[J]. The FASEB Journal, 2001, 15(13): 2533-2535.
[11] 曹智, 张治军. 防晒化妆品长波紫外线防护效果的仪器评价法[J]. 日用化学工业, 2009, 39(3): 196-199. Cao Z, Zhang Z J. Instrument assessment method for UVA protection effect of sunscreen cosmetics[J]. Daily Chemical Industry, 2009, 39(3): 196-199.
[12] Iwasaki Y, Tashiro K, Kikuchi S, et al. Cervical flexion myelopathy: a “tight dural canal mechanism” case report[J]. Journal of Neurosurgery, 1987, 66(6): 935-937.
[13] 姚孝元. 我国防晒化妆品中紫外线吸收剂分类和紫外吸收光谱[J]. 中国卫生检验杂志, 2005, 15(2): 236-241. Yao X Y. Category and UV absorption spectrum of UV filters in sunscreen cosmetics in China[J]. Chinese Journal of Health Laboratory Technology, 2005, 15(2): 236-241.
[14] Lang G, Maignan J, Malle G, et al. Bicyclic aromatic derivatives, method for preparing them, and their use in human and veterinary medicine and in cosmetics: U.S. Patent 4,833,240[P]. 1989-5-23.
[15] 白杨, 刘六军, 周调调, 等. 长叶烯制备异长叶烷酮的研究[J]. 精细与专用化学品, 2011, 19(2): 47-51. Bai Y, Liu L J, Zhou D D, et al. The research of isolongifolanone synthesized from longifolene[J]. Fine and Specialty Chemicals, 2011, 19(2): 47-51.
[16] 李明, 蒋凤池, 李希成. LiAlH_4 还原异长叶烷酮的反应[J]. 林产化学与工业, 1990(3): 13. Li M, Jiang F C, Li X C. The reduction reaction of isolongifolanone with LiAlH_4[J]. Chemistry and Industry Forest Products, 1990(3): 13.
[17] Dumitriu E, Hulea V, Fechete I, et al. The aldol condensation of lower aldehydes over MFI zeolites with different acidic properties[J]. Microporous and Mesoporous Materials, 2001, 43(3): 341-359.
[18] Guantai E M, Ncokazi K, Egan T J, et al. Enone-and chalcone-chloroquinoline hybrid analogues: In silicon guided design, synthesis, antiplasmodial activity, in vitro metabolism, and mechanistic studies[J]. Journal of Medicinal Chemistry, 2011, 54(10): 3637-3649.
[19] Ai M. Formation of acrylaldehyde by vapor-phase aldol condensation 1. Basin oxide catalysts[J]. Bulletin of the Chemical Society of Japan, 1991, 64(1): 1342-1345.
[20] Sebti S, Saber A, Rhihil A, et al. Claisen-Schmidt condensation catalysis by natural phosphate[J]. Applied Catalysis A: General, 2001, 206(2): 217-220.
[21] Scalia S, Casolari A, Iaconinoto A, et al. Comparative studies of the influence of cyclodextrins on the stability of the sunscreen agent, 2-ethylhexyl-p-methoxycinnamate[J]. Journal of Pharmaceutical and Biomedical Analysis, 2002, 30(4): 1181-1189.

7-芳亚甲基异长叶烷酮类化合物的合成及其紫外吸收特征

Synthesis and ultraviolet absorption characteristics of 7-arylidene-isolongifolanene

PDF

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 4

编辑推荐

Metrics

本文评价

作者

读者

审稿

[1]	魏丹萍, 叶建仁, 梁茂金, 陈飞飞. 瓦莱氏芽孢杆菌YH-18发酵液的喷雾干燥工艺[J]. 南京林业大学学报（自然科学版）, 2020, 44(5): 209-214.
[2]	曾健勇,于颖颖,张方明,李大波,张国财. 阿维菌素/乙基纤维素载药纤维的制备及稳定性分析[J]. 南京林业大学学报（自然科学版）, 2018, 42(06): 186-190.
[3]	徐鹏,王利莹,曹小勇,邵伟,唐进根. 乳化喷雾干燥法制备戊唑醇/壳聚糖微胶囊[J]. 南京林业大学学报（自然科学版）, 2017, 41(03): 157-161.
[4]	徐鹏,陈懿玺,唐进根,曹小勇,张蕤. 载Fe₃O₄纳米粒子磁性PLA微囊的制备[J]. 南京林业大学学报（自然科学版）, 2015, 39(04): 101-104.

7-芳亚甲基异长叶烷酮类化合物的合成及其 紫外吸收特征

Synthesis and ultraviolet absorption characteristics of 7-arylidene-isolongifolanene

PDF

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 4

编辑推荐

Metrics

本文评价

作者

读者

审稿

7-芳亚甲基异长叶烷酮类化合物的合成及其紫外吸收特征