2,6-dinitrobenzaldehyde -Drug Synthesis Database

【结构式】

【分子编号】39891

【品名】2,6-dinitrobenzaldehyde

【CA登记号】606-31-5

【分子式】C₇H₄N₂O₅

【分子量】196.11924

【元素组成】C 42.87% H 2.06% N 14.28% O 40.79%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

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).

参考文献中间体

合成目标

【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

合成路线2

该中间体在本合成路线中的序号：(I)

The Wittig reaction of 2,6-dinitrobenzaldehyde (I) with (ethoxycarbonylmethylene)triphenylphosphorane (A) produced methyl 2,6-dinitrocinnamate (II). Hydrogenation of the nitro groups and the olefinic double bond of (II) with concomitant cyclization furnished the tetrahydroquinolinone (III). Reductive alkylation of (III) with 6,6-dimethylheptadiynal (IV) and sodium cyanoborohydride produced the secondary amine (V). Finally, the N-methyl group was introduced by a second reductive alkylation with formaldehyde.

参考文献中间体

合成目标

【1】 Masabuchi, K.; Umeda, I.; Taniguchi, M.; et al.; Synthesis and structure-activity relationships of novel fungal chitin synthase inhibitors. Bioorg Med Chem Lett 2000, 10, 13, 1459.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	14689	Methyl (triphenylphosphoranylidene)acetate; (methoxycarbonylmethylene)triphenylphosphorane；Methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate	2605-67-6	C₂₁H₁₉O₂P	详情	详情
(I)	39891	2,6-dinitrobenzaldehyde	606-31-5	C₇H₄N₂O₅	详情	详情
(II)	44995	methyl (E)-3-(2,6-dinitrophenyl)-2-propenoate		C₁₀H₈N₂O₆	详情	详情
(III)	44996	5-amino-3,4-dihydro-2(1H)-quinolinone		C₉H₁₀N₂O	详情	详情
(IV)	44997	6,6-dimethyl-2,4-heptadiynal		C₉H₁₀O	详情	详情
(V)	44998	5-[(6,6-dimethyl-2,4-heptadiynyl)amino]-3,4-dihydro-2(1H)-quinolinone		C₁₈H₂₀N₂O	详情	详情

Extended Information