NMR Analysis of C60-Deisopropyldehydroabietylamine Derivative

doi:10.11938/cjmr20160216

Abstract

Abstract:

Cycloaddition reaction of C₆₀ with rosin compounds produces many functional fullerene derivatives. ¹H and ¹³C NMR spectra of the target compound N,N-tetrachlorophthaloyl-13-nitro-7,7-C₆₀-deisopropyldehydroabietylamine were collected and analyzed. The ¹H and ¹³C chemical shifts were assigned using two-dimensional NMR techniques, including ¹H-¹H COSY, ¹H-¹H ROESY, ¹H-¹³C HSQC and ¹H-¹³C HMBC. The spectral data obtained provided a reference for structure characterization of analogous compounds.

Key words: NMR, assignment, C₆₀-deisopropyldehydroabietylamine

CLC Number:

O482.53

ZHOU Zhi, LIN Zhong-xiang. NMR Analysis of C₆₀-Deisopropyldehydroabietylamine Derivative[J]. Chinese Journal of Magnetic Resonance, 2016, 33(2): 345-352.

References

[1] Sun Jian(孙健), Chen De-wen(陈德文), Liu Yang(刘杨), et al. ESR study of photoinduced electrontransfer reaction between C₆₀ and naphthylamine derivatives(C₆₀与某些萘胺衍生物光诱导电子转移反应的ESR研究)[J]. Chinese J Magn Reson(波谱学杂志), 1999, 16(4):331-334.

[2] Tang Guang-shi(唐光诗), Zhu He-sun(朱鹤孙), Dong Shu-an(董树安). The addition reaction of C₆₀(C₆₀的加成反应)[J]. Prog Chem(化学进展), 1997, 9(3):300-310.

[3] Shang Zhen-feng(尚贞锋), Pan Yin-ming(潘荫明), Wang Hai-xiang(王海翔), et al. Theoretical study on the addition reaction mechanisms of C₆₀(C₆₀加成反应的理论研究)[J]. Chem J Chinese U(高等学校化学学报), 1999, 20(3):432-435.

[4] Wang Fei(王飞), Zhou Qing-mei(周清梅), Zheng Li-ping(郑立平), et al. Synthesis of C₆₀ fullerene derivatives by azide alkyl cyclo-addition and their optoelectronic performance(叠氮烷烃环加成反应合成C₆₀衍生物及其聚合物太阳电池的特性)[J]. Chem J Chinese U(高等学校化学学报), 2005, 26(4):719-722.

[5] Ding Xia(丁霞), Lin Zhong-xiang(林中祥), Deng Hui-min(邓慧敏). Reaction of C₆₀ with abietic acid catalyzed by ZnCl₂(氯化锌催化下C₆₀与枞酸的反应)[J]. Chinese J Org Chem(有机化学), 2007, 27(2):252-254.

[6] Gao Jian(高健), Lin Zhong-xiang(林中祥), Deng Hui-min(邓慧敏), et al. Additive reaction of[60] fullerene and dehydroabietylamine under microwave irradiation(微波辐射下[60] 富勒烯与脱氢枞胺的加成反应)[J]. Mod Chem Ind(现代化工), 2007, 27(S1):266-268.

[7] Xiong Yao(熊垚), Lin Zhong-xiang(林中祥), Fan Xu(范旭), et al. Study on 1,3-dipolar cycloaddition of C₆₀ with N-carboxymethyl dehydroabietylamine(C₆₀与N-羧甲基脱氢枞胺的1,3-偶极环加成反应研究)[J]. Chemistry(化学通报), 2009, 72(5):474-477.

[8] Fan Xu(范旭), Lin Zhong-xiang(林中祥), Deng Hui-min(邓慧敏), et al. Synthesis and bioactivity study of water-soluble C₆₀-dehydroabietylamine derivatives(水溶性C₆₀-脱氢枞胺衍生物的合成及生物活性)[J]. J Nanjing Forestry Univ:Nat Sci Ed(南京林业大学学报:自然科学版), 2012, 36(2):29-34.

[9] Hu Jun-qiang(胡军强), Lin Zhong-xiang(林中祥). Synthesis and anti-HIV activity of a novel water-soluble C₆₀-dehydroabietylamine pyrrolidine derivative(新型水溶性C₆₀脱氢枞胺吡咯烷衍生物的合成及抗HIV活性)[J]. J Nanjing Forestry Univ:Nat Sci Ed (南京林业大学学报:自然科学版), 2013, 37(2):147-150.

[10] Zhou Zhi(周志), Lin Zhong-xiang(林中祥). Synthesis of 61-methyl-61-[12-(18-N-tetrachlorophthalimido) dehydroabietylamine]-1,2-methanofullerene[60] (61-甲基-61-[12-(18-N-四氯邻苯二甲酰亚氨基)脱氢枞胺]-1,2-亚甲基富勒烯[60] 的合成)[J]. Chemistry(化学通报), 2015, 78(1):80-84.

[11] Zhou Z, Lin Z X, Liang D, et al. First synthesis of ring-B C₆₀-substituted derivatives of N,N-(tetrachlorophthaloyl) dehydroabietylamine[J]. Tetrahedron, 2013, 69(1):43-49.

[12] Zhou Zhi(周志), Lin Zhong-xiang(林中祥). Synthesis of N,N-tetrachlorophthaloyl-13-nitro-7,7-C₆₀-deisopropyldehydroabietylamine(N,N-四氯邻苯二甲酰基-13-硝基-7,7-C₆₀-脱异丙基脱氢枞胺的合成)[J]. Chinese J Synth Chem(合成化学), 2014, 22(1):63-67.

[13] An Yan-peng(安艳捧), Yang Xiao-yan(杨晓艳), Li Hong-de(李洪德), et al. NMR analysis of nicotinamide N-Oxide and pseudouridine in rat urine(大鼠尿液中N-氧化烟酰胺和伪尿嘧啶核苷的NMR分析)[J]. Chinese J Magn Reson (波谱学杂志), 2014, 31(2):232-242.

[14] Ali I A I, Fathalla W. Synthesis of N-substituted-3,4,5,6-tetrachlorophthalimide using trichloroacetimidate C-C bond formation method[J]. Arkivoc, 2009, 13:193-199.

[15] Liu Shu-zhi(刘书芝), Tang Guang-shi(唐光诗). Symmetry, cage structure of[60] fullerene derivatives and ¹³C NMR spectroscopy([60] 富勒烯衍生物的对称性、碳笼结构与¹³C NMR谱)[J]. Prog Chem(化学进展), 2004, 16(4):561-573.

NMR Analysis of C₆₀-Deisopropyldehydroabietylamine Derivative

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