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【结 构 式】 
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【分子编号】24299 【品名】1-(4-iodophenyl)acetone 【CA登记号】 |
【 分 子 式 】C9H9IO 【 分 子 量 】260.07433 【元素组成】C 41.56% H 3.49% I 48.8% O 6.15% |
合成路线1
该中间体在本合成路线中的序号：(VIII)2) A route that does not involve controlled drugs (phenylacetone or amphetamine) proceeds from p-iodophenylacetic acid (VII). The starting material can be made in low yield by iodination of phenylacetic acid or by a two-step process from p-aminophenylacetic acid by diazotization and treatment with potassium iodide. Condensation of p-iodophenylacetic acid (VII) with acetic anhydride gives p-iodophenylacetone (VIII) in variable yields, depending on the purity of the starting carboxylic acid and en the choice of base. Reductive amination with isopropylamine then gives iofetamine (V) in good yield.
| 【1】 Stoermer, R.; Strioh, H.; Die Phenylbenzylbernsteinsaueren. Chem Ver 1935, 68, 2112. |
| 【2】 King, J.A.; Mc Millan, F.H.; The decarboxylate acylation of arylacetic acids. J Am Chem Soc 1951, 73, 6911, 4911. |
| 【3】 Lucas, H.J.; Kennedy, E.R.; Iodobenzene. Org Synth Coll 1943, II, 5, 351. |
| 【4】 Cavallini, G.; Massarani, E.; Nardi, D.; Applicazione dell reazione di Leukart ad alcuni fenil propan-2-oni sostituti in posizione para. Farm Sci Ed 1956, 11, 805. |
| 【5】 Andresen, K.; Carlsen, L.; 131I-labelled N-isopropyl-p-Iodoamphetamine. Eur J Nucl Med 1982, 7, 6, 280. |
| 【6】 Baldwin, R.M.; Iofetamine (123I) hydrochloride. Drugs Fut 1986, 11, 8, 652. |
合成路线2
该中间体在本合成路线中的序号：(VIII)3) A third sequence proceeds by condensation of p-iodobenzaldehyde (IX) with nitromethane, followed by reductive hydrolysis of the intermediate unsaturated nitrocompound, to yield p-iodophenylacetone (VIII). The final sequence is the same as in scheme 09034702a.
| 【1】 le Poncin-Lafitte, M.; Duterte, D.; Morier, E.; et al.; Synthesis of p-I-125 amphetamine. J Label Compd Radiopharm 1983, 20, 149. |
| 【2】 Coornaert, S.; Rapin, J.R.; Bardy, A.; et al.; New ways of obtaining N-isopropyl-p-iodoamphetamine and pharmacokinetic studies in rat. 3rd Wordl Cong Nucl Med Biol (Aug, Paris) 1982, 4, 23, 3598. |
| 【3】 Rapin, J.R.; et al.; Chemical and pharmacological aspects of cerebral cellular tracers. Ann Radiol 1983, 26, 1, 48. |
| 【4】 Baldwin, R.M.; Iofetamine (123I) hydrochloride. Drugs Fut 1986, 11, 8, 652. |