【结 构 式】 |
【分子编号】31312 【品名】2,3-diethyl-1,2,3,4-tetrahydro-7-quinolinylamine; 2,3-diethyl-1,2,3,4-tetrahydro-7-quinolinamine 【CA登记号】 |
【 分 子 式 】C13H20N2 【 分 子 量 】204.31528 【元素组成】C 76.42% H 9.87% N 13.71% |
合成路线1
该中间体在本合成路线中的序号:(X)Conjugate addition of pentenoic acid (I) to aniline (II) gave amino acid (III), which was cyclized to the quinolinone (IV) with polyphosphoric acid at 110 C. Protection of the amino group of (IV) with Boc2O gave carbamate (V), which was subsequenty alkylated with iodoethane in the presence of NaH to yield (VI) as a diastereomeric mixture. Acid deprotection of the Boc group of (VI) gave amine (VII). The ketone group of (VII) was then reduced with triethylsilane and boron trifluoride to the tetrahydroquinoline (VIII). Nitration of (VIII), followed by hydrogenation of the resulting nitro derivative (IX) furnished the aminoquinoline (X). Further Knorr cyclization of (X) with ethyl 4,4,4-trifluoroacetoacetate (XI) by means of ZnCl2 in refluxing EtOH yielded the corresponding pyridoquinoline. The required trans isomer was finally isolated by preparative HPLC.
【1】 Zhi, L.; Marschke, K.B.; Jones, T.K.; Tegley, C.M.; Switching androgen receptor antagonists to agonists by modifying C-ring substituents on piperidino[3,2-g]quinolinone. Bioorg Med Chem Lett 1999, 9, 7, 1009. |
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) | 31305 | (E)-2-pentenoic acid | 13991-37-2 | C5H8O2 | 详情 | 详情 |
(II) | 12294 | Aniline; Phenylamine | 62-53-3 | C6H7N | 详情 | 详情 |
(III) | 31306 | 3-anilinopentanoic acid | C11H15NO2 | 详情 | 详情 | |
(IV) | 31307 | 2-ethyl-2,3-dihydro-4(1H)-quinolinone | C11H13NO | 详情 | 详情 | |
(V) | 31308 | tert-butyl 2-ethyl-4-oxo-3,4-dihydro-1(2H)-quinolinecarboxylate | C16H21NO3 | 详情 | 详情 | |
(VI) | 31309 | tert-butyl 2,3-diethyl-4-oxo-3,4-dihydro-1(2H)-quinolinecarboxylate | C18H25NO3 | 详情 | 详情 | |
(VII) | 31310 | 2,3-diethyl-2,3-dihydro-4(1H)-quinolinone | C13H17NO | 详情 | 详情 | |
(VIII) | 31311 | 2,3-diethyl-1,2,3,4-tetrahydroquinoline | C13H19N | 详情 | 详情 | |
(IX) | 31313 | 2,3-diethyl-7-nitro-1,2,3,4-tetrahydroquinoline | C13H18N2O2 | 详情 | 详情 | |
(X) | 31312 | 2,3-diethyl-1,2,3,4-tetrahydro-7-quinolinylamine; 2,3-diethyl-1,2,3,4-tetrahydro-7-quinolinamine | C13H20N2 | 详情 | 详情 | |
(XI) | 25432 | ethyl 4,4,4-trifluoro-3-oxobutanoate | 372-31-6 | C6H7F3O3 | 详情 | 详情 |