Beilstein J. Org. Chem. 2012, 8, 11–17.
white solid (1.63 g, 2.30 mmol, 61%); mp 136 °C; 1H NMR this 13C spectrum. MS (MALDI-TOF, Cl-CCA): m/z 676 [M +
(500 MHz, CDCl3) δ 8.18 (s, 1H, Ar1-2-H), 8.08 (s, 2H, Ar1- Na]+, 654 [M + H]+.
4,6-H), 7.28 (br. s, 2H, NH), 7.16 (t, 3J = 8.4 Hz, 2H, Ar2-4-H),
6.59 (d, 3J = 8.4 Hz, 4H, Ar2-3,5-H), 5.78 (ddt, 3J = 16.9 Hz, 3J
Supporting Information
= 10.2 Hz, 3J = 6.6 Hz, 4H, CH=CH2), 4.97 (mc, 4H, HZ), 4.91
(mc, 4H, HE), 4.01 (t, 3J = 6.5 Hz, 8H, OCH2), 2.16 (mc, 8H,
NMR spectra and product analyses for 1 and 2 are available
CH2CH=CH2), 1.85 (mc, 8H, OCH2CH2), 1.38 (s, 9 H,
in the Supporting Information as well as details of the
CH3).13C NMR (125 MHz, CDCl3) δ 166.1 (s, C=O), 154.8 (s,
NMR CIS titrations, the evaluation of the normalized CIS
Ar2-2,6-C), 152.3 (s, Ar1-5-C), 137.6 (d, CH=CH2), 135.4 (s,
method, 1H,1H NOESY experiments, and the transport
Ar1-1,3-C), 127.6 (d, Ar1-4,6-C), 127.6 (d, Ar2-4-C) 123.3 (d,
experiments.
Ar1-2-C), 115.1 (t, CH=CH2), 106.2 (s, Ar2-1-C), 105.4 (d, Ar2-
Supporting Information File 1
3,5-C), 68.1 (t, OCH2), 35.1 (s, C(CH3)3), 31.2 (q, CH3), 30.1
(t, CH2CH=CH2), 28.4 (t, OCH2CH2); IR (ATR) : 3207 (br.
w, NH), 3076 (w, arom. CH), 2946 (m, aliph. CH), 1669 (m,
C=O), 1647 (m, aliph. C=C), 1589 (m, arom. C=C), 1520 (s,
arom. C=C) cm−1; EIMS (70 eV): m/z (% relative intensity) 709
(49) [M]+•, 708 (100) [M − H]+; CIMS (isobutane): m/z (%
Product analyses and experimental data.
relative intensity) 710 (25) [M + H]+, 709 (59) [M]+•, 708 (100) Acknowledgements
[M − H]+; ESIMS (CHCl3): m/z (% relative intensity) 732 (25) We thank Dr. Roberto Quesada, University of Burgos, Spain,
[M + Na]+; HRMS: calcd for C44H56N2O6: 708.41382; found: for the chloride transport experiments, and the EU for its
708.41390 (Δ = −0.1 ppm); calcd for C4313CH56N2O6: support through the Marie Curie Research Training Network
709.41718; found: 709.41706 (Δ = 0.2 ppm). Anal. calcd for MRTN-CT-2006-035614 Dynamic Combinatorial Chemistry
C44H56N2O6·0.3C6H12·0.3C4H8O2: C, 74.18; H, 8.24; N, 3.66; (DCC).
found: C, 73.95; H, 7.93; N, 4.04.
References
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Synthesis of 255-tert-Butyl-2,11,13,22-tetraoxa-
23,27-diaza-1,12(1,3,2)-25(1,3)-
tribenzenabicyclo[10.10.5]heptacosaphan-6,17-
dien-24,26-dione
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Anhydrous dichloromethane (800 mL) was added to a mixture
of N,N'-bis-(2,6-bis[pent-4-enyloxy]-phenyl)-5-tert-butyl-iso-
phthalamide (5, 1.00 g, 1.41 mmol) and Grubbs Catalyst 1st
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product was filtered off and washed with ethyl acetate (10 mL)
to obtain a white solid (186 mg, 284 µmol, 20%). 1H NMR
(500 MHz, CDCl3) δ 8.25 (s, 2H, 254,6-H), 7.98 (s, 1H, 252-H),
7.20 (br. s, 2H, NH), 7.15 (t, 3J = 8.3 Hz, 2H, 15,125-H), 6.61
(d, 3J = 8.3 Hz, 4H, 14,6,124,6-H), 5.36–5.27 (m, 4H, CH=CH),
4.22–3.82 (m, 8H, OCH2), 2.20–1.60 (m, 16H, CH2), 1.42 (s,
9H, CH3) ppm; 13C NMR (125 MHz, CDCl3) δ 154.2 (s,
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CH=CH), 129.6 (d, 254,6-C), 127.0 (d, 15,125-C), 121.7 (d, 252-
C), 116.1 (s, 12,122-C), 105.4 (d, 14,6,124,6-C), 69.5 (t, OCH2),
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O(CH2)2CH2); The C=O signal was too weak to be detected in
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