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【结 构 式】 
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【分子编号】39892 【品名】2-(2,6-dinitrophenyl)-1,3-dioxolane 【CA登记号】 |
【 分 子 式 】C9H8N2O6 【 分 子 量 】240.1724 【元素组成】C 45.01% H 3.36% N 11.66% O 39.97% |
合成路线1
该中间体在本合成路线中的序号：(IV)This compound can be obtained in two different ways: 1) By direct nitration of camptothecin (I) with nitric acid in sulfuric acid. 2) By direct nitration of camptothecin (I) with different inorganic nitrates (or mixtures of inorganic nitrates) in sulfuric acid. 3) The reaction of 2,6-dinitrobenzaldehyde (II) with ethylene glycol (III) and p-toluenesulfonic acid in refluxing toluene gives the corresponding ethylene ketal (IV), which is reduced with sodium sulfide in refluxing ehanol/water yielding 2-amino-6-nitrobenzaldehyde ethylene ketal (V). The hydrolysis of (V) with aqueous sulfuric acid affords 2-amino-6-nitrobenzaldehyde (VI), which is finally cyclized with the tricyclic ketone (VII) in refluxing acetic acid (the same cyclization can be performed with the ketal (V) and the ketone (VII).
| 【1】 Cao, Z.S.; et al.; Nitration of campothecin with various inorganic nitrate salts in concentrated sulfuric acid: A new preparation of anticancer drug 9-nitrocamptothecin. Synthesis 1998, 12, 1724. |
| 【2】 Sawada, S.; Matsuoka, S.-I.; Nokata, K.-I.; Nagata, H.; Furuta, T.; Yokokura, T.; Miyasaka, T.; Synthesis and antitumor activity of 20(S)-camptothecin derivatives: A-ring modified and 7,10-disubstituted camptothecins. Chem Pharm Bull 1991, 39, 12, 3183. |
| 【3】 Wani, M.C.; Nicholas, A.W.; Wall, M.E.; Plant antitumor agents. 23. Synthesis and antileukemic activity of camptothecin analogues. J Med Chem 1986, 29, 11, 2358. |
| 【4】 Leitner, P.; Tele, C.; Truesdale, A.; Nicholas, A.W.; Moore, L.; Besterman, J.M.; Manikumar, G.; Wani, M.C.; Wall, M.E.; Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs. J Med Chem 1993, 36, 18, 2689. |
| 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) | 10816 | Camptothecin; (4S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 4-et-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo(b,h)fluorene-3,13-dione | 7689-03-4 | C20H16N2O4 | 详情 | 详情 |
| (II) | 39891 | 2,6-dinitrobenzaldehyde | 606-31-5 | C7H4N2O5 | 详情 | 详情 |
| (III) | 11295 | Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol | 107-21-1 | C2H6O2 | 详情 | 详情 |
| (IV) | 39892 | 2-(2,6-dinitrophenyl)-1,3-dioxolane | C9H8N2O6 | 详情 | 详情 | |
| (V) | 39893 | 2-(1,3-dioxolan-2-yl)-3-nitrophenylamine; 2-(1,3-dioxolan-2-yl)-3-nitroaniline | C9H10N2O4 | 详情 | 详情 | |
| (VI) | 15649 | 2-amino-6-nitrobenzaldehyde | C7H6N2O3 | 详情 | 详情 | |
| (VII) | 10841 | (4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione | C13H13NO5 | 详情 | 详情 |