.
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.
http://www.mdpi.com/1420-3049/17/4/4209/htm
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C | δC (ppm) | H | δH (ppm) | HSQC | HMBC | COSY | ROESY |
---|---|---|---|---|---|---|---|
1 | 39.48 | 1β | 2.39 (br d, J = 11.9 Hz) | H-1β, 1α | H-20, 2, 3α | H-1α, 2 | H-20, 11, 2, 1α |
1α | 1.79–1.74 (m) | H-1β, 2 | H-5, 11, 1β | ||||
2 | 18.18 | 2 | 1.85–1.79 (m, 2H) | H-2 | H-3β, 3α, 1β, 1α | H-19, 3β, 3α, 1β | |
3 | 37.52 | 3β | 1.58 (br d, J = 13.0 Hz) | H-3β, 3α | H-19, 18α, 18β | H-3α, 2 | H-19, 3α, 2 |
3α | 1.53–1.47 (m) | H-3β, 2 | H-5, 18α, 3β, 2 | ||||
4 | 40.89 | ― | ― | ― | H-19, 5, 18α, 18β, 6β | ― | ― |
5 | 48.67 | 5 | 1.97 (dd, J = 10.3, 9.2 Hz) | H-5 | H-19, 20, 18α, 18β, 6α, 6β | H-6β, 6α | H-3α, 1α, 6α, 18α, 2 |
6 | 28.35 | 6β | 3.65 (dd, J = 14.1, 10.5 Hz) | H-6β, 6α | C-6/H-5 | H-5, 6α | H-19, 20, 6α |
6α | 3.41 (dd, J = 14.1, 8.8 Hz) | H-5, 6β | H-5, 6β, 18α | ||||
7 | 44.61 | ― | ― | ― | H-6α, 6β, 14, 11 | ― | ― |
8 | 132.15 | ― | ― | ― | H-6β, 11, | ― | ― |
9 | 150.35 | ― | ― | ― | H-14, 12, 20, 5 | ― | ― |
10 | 38.83 | ― | ― | ― | H-20, 5, 6α, 2, 11 | ― | ― |
11 | 123.40 | 11 | 7.43 (d, J = 8.1 Hz) | H-11 | H-12 | H-12 | H-1β, 1α, 12 |
12 | 126.09 | 12 | 7.28 (dd, J = 8.1, 1.8 Hz) | H-12 | H-15, 11, 14 | H-11 | H-15, 11, 16 |
13 | 145.43 | ― | ― | ― | H-16, 17, 15, 11 | ― | ― |
14 | 126.42 | 14 | 8.40 (d, J = 1.8 Hz) | H-14 | H-12, 15 | ― | ― |
15 | 33.92 | 15 | 2.99 (septet, J = 6.7 Hz) | H-15 | H-16, 17, 12, 14 | H-16, 17 | H-16, 17, 12 |
16 | 23.70 | 16 | 1.30 (d, J = 6.8 Hz, 3H) | H-16 | H-15, 17, | H-15 | H-15, 12 |
17 | 24.49 | 17 | 1.32 (d, J = 7.0 Hz, 3H) | H-17 | H-15, 16 | H-15 | H-15 |
18 | 50.45 | 18β | 3.88 (d, J = 13.6 Hz) | H-18β, 18α | H-19, 5 | H-18α | H-18α, 19 |
18α | 3.59 (d, J = 13.6 Hz) | H-18β | H-18β, 5, 3α, 6α | ||||
19 | 18.89 | 19 | 1.31 (s, 3H) | H-19 | H-5, 18α, 18β | ― | H-20, 6β, 18β, 3β, 2 |
20 | 22.50 | 20 | 1.86 (s, 3H) | H-20 | H-1α, 5 | ― | H-19, 6β, 1β |
21,22 | 84.80 | ― | ― | ― | H-6α, 6β | ― | ― |
77.66 | ― | ― | ― | H-6α | ― | ― | |
1',6' | 127.52 | ― | ― | ― | ― | ― | ― |
2',5' | 129.76 | ― | ― | ― | ― | ― | ― |
3',4' | 140.35 | ― | ― | ― | ― | ― | ― |
7',8' | 164.51 | ― | ― | ― | H-18α, 18β | ― | ― |
C60 | 150.74–137.82 | ― | ― | ― | ― | ― | ― |
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
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///////