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7-C60-adduct of N,N-(tetrachlorophthaloyl)dehydroabietylamine

Molecules 17 04209 g001 1024.





Scheme 1. Preparation of compound 5.
Molecules 17 04209 g004 1024





Table 1. 1H- and 13C-NMR data, 1H-1H correlations in COSY, ROESY spectra and 1H-13C correlations in HSQC, HMBC spectra for compound 5.
CδC (ppm)HδH (ppm)HSQCHMBCCOSYROESY
139.481β2.39 (br d, J = 11.9 Hz)H-1β, 1αH-20, 2, 3αH-1α, 2H-20, 11, 2, 1α
1α1.79–1.74 (m) H-1β, 2H-5, 11, 1β
218.1821.85–1.79 (m, 2H)H-2 H-3β, 3α, 1β, 1αH-19, 3β, 3α, 1β
337.523β1.58 (br d, J = 13.0 Hz)H-3β, 3αH-19, 18α, 18βH-3α, 2H-19, 3α, 2
3α1.53–1.47 (m) H-3β, 2H-5, 18α, 3β, 2
440.89H-19, 5, 18α, 18β, 6β
548.6751.97 (dd, J = 10.3, 9.2 Hz)H-5H-19, 20, 18α, 18β, 6α, 6βH-6β, 6αH-3α, 1α, 6α, 18α, 2
628.356β3.65 (dd, J = 14.1, 10.5 Hz)H-6β, 6αC-6/H-5H-5, 6αH-19, 20, 6α
6α3.41 (dd, J = 14.1, 8.8 Hz) H-5, 6βH-5, 6β, 18α
744.61H-6α, 6β, 14, 11
8132.15H-6β, 11,
9150.35H-14, 12, 20, 5
1038.83H-20, 5, 6α, 2, 11
11123.40117.43 (d, J = 8.1 Hz)H-11H-12H-12H-1β, 1α, 12
12126.09127.28 (dd, J = 8.1, 1.8 Hz)H-12H-15, 11, 14H-11H-15, 11, 16
13145.43H-16, 17, 15, 11
14126.42148.40 (d, J = 1.8 Hz)H-14H-12, 15
1533.92152.99 (septet, J = 6.7 Hz)H-15H-16, 17, 12, 14H-16, 17H-16, 17, 12
1623.70161.30 (d, J = 6.8 Hz, 3H)H-16H-15, 17, H-15H-15, 12
1724.49171.32 (d, J = 7.0 Hz, 3H)H-17H-15, 16H-15H-15
1850.4518β3.88 (d, J = 13.6 Hz)H-18β, 18αH-19, 5 H-18αH-18α, 19
18α3.59 (d, J = 13.6 Hz) H-18βH-18β, 5, 3α, 6α
1918.89191.31 (s, 3H)H-19H-5, 18α, 18βH-20, 6β, 18β, 3β, 2
2022.50201.86 (s, 3H)H-20H-1α, 5H-19, 6β, 1β
21,2284.80H-6α, 6β
77.66H-6α
1',6'127.52
2',5'129.76
3',4'140.35
7',8'164.51H-18α, 18β
C60150.74–137.82


Figure 2. 1H-NMR spectrum of compound 5.
Molecules 17 04209 g002 1024


Figure 3. 13C-NMR spectrum of compound 5.
Molecules 17 04209 g003 1024


 5 as a dark brown solid (145 mg, 41%). IR νmax/cm−1: 3430, 2923, 2858, 1776, 1721, 1628, 1559, 1514, 1459, 1427, 1372, 1334, 1163, 1059, 893, 825, 740, 555, 526, 472; UV-vis (CHCl3) λmax (nm): 697.00, 493.00, 436.50; 1H-NMR: δ 8.40 (d, J = 1.8 Hz, 1H), 7.43 (d, J = 8.1 Hz, 1H), 7.28 (dd, J = 8.1, 1.8 Hz, 1H), 3.88 (d, J = 13.6 Hz, 1H), 3.65 (dd, J = 14.1, 10.5 Hz, 1H), 3.59 (d, J = 13.6 Hz, 1H), 2.99 (septet, J = 6.7 Hz, 1H), 2.39 (br d, J = 11.9 Hz, 1H), 1.97 (dd, J = 10.3, 9.2 Hz, 1H), 1.86 (s, 3H), 1.85–1.79 (m, 2H), 1.79–1.74 (m, 1H), 1.58 (br d, J = 13.0 Hz, 1H), 1.53–1.47 (m, 1H), 1.32 (d, J = 7.0 Hz, 3H), 1.31 (s, 3H), 1.30 (d, J = 6.8 Hz, 3H); 13C-NMR: δ 164.51 (2C=O, imide), 150.74, 150.35, 149.89, 147.97, 147.53, 145.99, 145.92, 145.43, 145.27, 145.24, 145.21, 145.17, 145.02, 144.96, 144.89, 144.78, 144.68, 144.21, 144.19, 143.97, 143.87, 143.68, 143.25, 143.19, 143.16, 143.06, 143.01, 142.84, 142.76, 142.24, 142.18, 142.13, 142.06, 141.87, 141.40, 141.15, 141.04, 140.84, 140.35 (2C, -N(CO)2C6Cl4), 140.22, 138.59, 138.51, 137.94, 137.82, 132.15, 129.76 (2C, -N(CO)2C6Cl4), 127.52 (2C, -N(CO)2C6Cl4), 126.42, 126.09, 123.40, 84.80, 77.66, 50.45, 48.67, 44.61, 40.89, 39.48, 38.83, 37.52, 33.92, 28.35, 24.49, 23.70, 22.50, 18.89, 18.18; MALDI-TOF MS (matrix: CHCA, reflectron negative) m/z 1269.4 M(35Cl4), 1271.4 M(35Cl337Cl), 1273.4 M(35Cl237Cl2), 1275.4 M(35Cl37Cl3); Anal. Calcd for C88H27Cl4NO2 (1271.97): C, 83.09; H, 2.14; N, 1.10. Found: C, 82.48; H, 2.20; N, 1.04.


Molecules 2012, 17(4), 4209-4218; doi:10.3390/molecules17044209
Synthesis and NMR Spectral Studies of the 7-C60-Adduct of N,N-(Tetrachlorophthaloyl) Dehydroabietylamine
Zhi Zhou 1,2,* and Zhongxiang Lin 1
1
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
2
College of Life and Environmental Sciences, Kaili University, Kaili, Guizhou 556011, China
*
Author to whom correspondence should be addressed; Email: Tel./Fax: +86-25-8542-7065.
Received: 4 March 2012; in revised form: 25 March 2012 / Accepted: 27 March 2012 / Published: 5 April 2012

Abstract

: The 7-C60-adduct of N,N-(tetrachlorophthaloyl)dehydroabietylamine was synthesized for the first time and characterized by IR, UV-vis, mass and NMR spectral studies. The 1H-NMR and 13C-NMR resonance signals of the new compound are unambiguously assigned by using homo- and heteronuclear 2D NMR spectroscopic techniques such as COSY, ROESY, HSQC and HMBC. The C1 symmetric structure with 6,6-junction of compound was determined.
Keywords:
7-C60-adduct of N,N-(tetrachlorophthaloyl)dehydroabietylamine; 1H-NMR; 13C-NMR; 2D NMR; C1 symmetric structure
 http://www.mdpi.com/1420-3049/17/4/4209/htm

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