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【结 构 式】 
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【分子编号】14850 【品名】7-hydroxy-2,2,4,6-tetramethyl-1-indanone oxime 【CA登记号】 |
【 分 子 式 】C13H17NO2 【 分 子 量 】219.28352 【元素组成】C 71.21% H 7.81% N 6.39% O 14.59% |
合成路线1
该中间体在本合成路线中的序号：(IV)Alkylation of 4,6-dimethyl-7-hydroxy-1-indanone (I) with methyliodide and sodium hydride in DMF affords 7-methoxy-2,2,4,6-tetramethyl-1-indanone (II), which is demethylated with aluminum chloride in CH3CN to give 7-hydroxy-2,2,4,6-tetramethyl-1-indanone (III). Oxime formation with hydroxylamine hydrochloride in pyridine yields 7-hydroxy-2,2,4,6-tetramethyl-1-indanone oxime (IV), which on treatment with hydrogen in the presence of platinum oxide in acetic acid gives 1-amino-7-hydroxy-2,2,4,6-tetramethylindan (V) (1, 3). Acetylation of (V) with chloroacetyl chloride and triethylamine gives 2-chloro-N-(7-hydroxy-2,2,4,6-tetramethylindan-1-yl)acetamide (VI), which is finally condensed with 1-(3-methoxyphenyl)piperazine (VII) in acetonitrile.
| 【1】 Oshiro, Y.; Ueda, H.; Nakagawa, K. (Otsuka Pharmaceutical Co., Ltd.); 2,3-Dihydro-1H-indene derivs., a process for preparing them and pharmaceutical compsns. containing same. EP 0173331; ES 8800121; ES 8800884; ES 8801180; JP 1986069747; JP 1987129258; JP 1993004950; US 4788130; US 4895847; US 5242919 . |
| 【2】 Oshiro, Y.; Tottori, K.; Tanaka, T.; Kikuchi, T.; Sakurai, Y.; Ueda, H.; Novel cerebroprotective agents with central nervous system stimulating activity. 1. Synthesis and pharmacology of 1-amino-7-hydroxyindan derivatives. J Med Chem 1991, 34, 7, 2004-13. |
| 【3】 Mealy, N.; Prous, J.; Castaner, J.; OPC-14117. Drugs Fut 1993, 18, 8, 707. |
| 【4】 Tottori, K.; Tanaka, T.; Hirose, T.; Sakurai, Y.; Kikuchi, T.; Oshiro, Y.; Novel cerebroprotective agents with central nervous system stimulating activity. 2. Synthesis and pharmacology of the 1-(acylamino)-7-hydroxyindan derivatives. J Med Chem 1991, 34, 7, 2014-23. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 14847 | 7-hydroxy-4,6-dimethyl-1-indanone | C11H12O2 | 详情 | 详情 | |
| (II) | 14848 | 7-methoxy-2,2,4,6-tetramethyl-1-indanone | C14H18O2 | 详情 | 详情 | |
| (III) | 14849 | 7-hydroxy-2,2,4,6-tetramethyl-1-indanone | C13H16O2 | 详情 | 详情 | |
| (IV) | 14850 | 7-hydroxy-2,2,4,6-tetramethyl-1-indanone oxime | C13H17NO2 | 详情 | 详情 | |
| (V) | 14851 | 3-amino-2,2,5,7-tetramethyl-4-indanol | C13H19NO | 详情 | 详情 | |
| (VI) | 14852 | 2-chloro-N-(7-hydroxy-2,2,4,6-tetramethyl-2,3-dihydro-1H-inden-1-yl)acetamide | C15H20ClNO2 | 详情 | 详情 | |
| (VII) | 14853 | methyl 3-piperazinophenyl ether; 1-(3-methoxyphenyl)piperazine | 16015-71-7 | C11H16N2O | 详情 | 详情 |