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【结 构 式】 
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【分子编号】44689 【品名】2-ethyl-1H-isoindole-1,3(2H)-dione 【CA登记号】 |
【 分 子 式 】C10H9NO2 【 分 子 量 】175.187 【元素组成】C 68.56% H 5.18% N 8% O 18.27% |
合成路线1
该中间体在本合成路线中的序号：(XII)2) Hexadeuteroethyl alcohol (IX) is treated with red phosphorus and I2 at reflux temperature to give pentadeuteroethyl iodide (X), which is condensed with potassium phthalimide (XI) in DMF, yielding N-(pentadeuteroethyl)phthalimide (XII). The hydrolysis of (XII) with hydrazine and HCl affords pentadeuteroethylamine (XIII), which is condensed with 1-methylpiperidin-4-one (III) and formaldehyde (XIV) in a Mannich reaction to give 3-methyl-7-(pentadeuteroethyl)-3,7-diazabicyclo[3.3.1]nonan-9-one (XV). The reduction of (XV) with NaBH4 as before yields the diastereomeric mixture (XVI + XVII). Finally, the alpha-isomer (XVI) is condensed with 4-chlorobenzoyl chloride (VIII) as before to give the pentadeuterium-labeled bisaramil.
| 【1】 Mlinko, S.; Simon Trompler, E.; Szammer, J.; Synthesis of bisaramil labelled with carbon-14 and deuterium. J Label Compd Radiopharm 1994, 34, 4, 313. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 10919 | 1-Methyl-4-piperidone; 1-Methyltetrahydro-4(1H)-pyridinone; N-Methyl-4-piperidone;1-methylpiperidin-4-one | 1445-73-4 | C6H11NO | 详情 | 详情 |
| (VIII) | 10295 | p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride | 122-01-0 | C7H4Cl2O | 详情 | 详情 |
| (IX) | 10924 | Ethyl alcohol; Ethanol | 1516-08-1 | C2H6O | 详情 | 详情 |
| (IX) | 44687 | Ethanol-d6 | C2H6O | 详情 | 详情 | |
| (X) | 10925 | Iodoethane;ethyl iod | 75-03-6 | C2H5I | 详情 | 详情 |
| (X) | 44688 | 1-iodoethane-d5 | C2H5I | 详情 | 详情 | |
| (XI) | 10926 | (1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)potassium | C8H4KNO2 | 详情 | 详情 | |
| (XII) | 10927 | 2-Ethyl-1H-isoindole-1,3(2H)-dione | 5022-29-7 | C10H9NO2 | 详情 | 详情 |
| (XII) | 44689 | 2-ethyl-1H-isoindole-1,3(2H)-dione | C10H9NO2 | 详情 | 详情 | |
| (XIII) | 10928 | Ethanamine | 75-04-7 | C2H7N | 详情 | 详情 |
| (XIII) | 44690 | ethylamine; 1-ethanamine | C2H7N | 详情 | 详情 | |
| (XV) | 10929 | 3-Ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one | C10H18N2O | 详情 | 详情 | |
| (XV) | 44691 | 3-ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one | C10H18N2O | 详情 | 详情 | |
| (XVI) | 10921 | 3-Ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-ol | C10H20N2O | 详情 | 详情 | |
| (XVI) | 44692 | 3-ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-ol | C10H20N2O | 详情 | 详情 | |
| (XVII) | 10922 | 3-Ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-ol | C10H20N2O | 详情 | 详情 | |
| (XVII) | 44693 | 3-ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-ol | C10H20N2O | 详情 | 详情 |