Reference of 16355-92-3,Some common heterocyclic compound, 16355-92-3, name is 1,10-Diiododecane, molecular formula is C10H20I2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Example 9 (n=10); (a) 1, 1′-[(Decane-1,10-diyl)dioxy]bis[(11S,11aS)-10-(tert- butylOxyCarbonyl)-8-methoxy-11-(tetrahydro-pyran-2-ylOxy)- 1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5- one] (8h); 1,10-Diiododecane (87.8 mg, 0.22 mmol, 0.5 equiv) was added to the mixture of monomer 7 (0.2 g, 0.44 mmol, 1.0 equiv) and potassium carbonate (0.98 mmol, 2.2 equiv) in dry DMF (30 mL), and the resulting mixture was heated to 90C under a nitrogen atmosphere for 5 h. Removal of excess solvent under reduced pressure afforded a crude solid, which was subjected to flash column chromatography (Si02, 50% EtOAc-hexane) to afford the dimerized compound 8h (191 mg, 0.1 8mmol, 82% yield, mixture of diastereomers from THP protecting group) as a solid: [a] 20D = +75 (c = 0.10, CHCl3); 1H NMR (CDCl3, 400 MHz): 5 1.25-1. 59 (m, 76H, 14-H, 15-H, 16-H, Boc, THP), 1. 68-1. 92 (16H, 13-H, THP), 1. 93-2. 20 (m, 16H, 1-H, 2-H), 3.45- 3.75 (m, 16H, 3-H, lla-H, THP), 3.83-4. 14 (m, 24H, 12-H, 7-OMe, THP), 5.02-5. 10 (m, 2H, THP), 5.12-5. 19 (m, 2H, THP), 5.69-5. 77 (d, 2H, 11-H), 5.79-5. 89 (d, 2H, 11-H), 6.49 (s, 2H, 9-H), 6. 86 (s, 2H, 9-H), 7.17 (s, 2H, 6-H), 7.21 (s, 2H, 6-H) ; 13C NMR (CDCl3, 400 MHz): 5 19. 9, 20.4, 23.1, 23.2, 25.2, 25.3, 25.9, 28.1, 28.2, 28. 9,29. 0,29. 1,29. 2,29. 3,29. 5,30. 9,31. 3,46. 3, 55. 9, 56. 2, 60. 0,60. 1, 63.3, 69. 1, 80.9, 81.2, 88.2, 91.2, 95. 8, 100. 2, 111.1, 111.5, 113.4, 114.0, 121.6, 126. 4,141. 0,143. 1,148. 1, 148.4, 155.4, 167.4, 167.6 ; IR (neat): 2937,1703, 1643, 1604, 1513,1450, 1392,1327, 1218,1164, 1022cm~1 ; MS (FAB) m/z (relative intensity) 1057 ( [M + Na] +’, 34), 1035 (M+., 100), 833 (26), 933 (25).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,10-Diiododecane, its application will become more common.
Reference:
Patent; SPIROGEN LIMITED; WO2005/85259; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com