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【结 构 式】 
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【分子编号】41616 【品名】4,8,8-trimethyl-1,8-dihydro-2H-pyrano[2,3-h]quinolin-2-one 【CA登记号】 |
【 分 子 式 】C15H15NO2 【 分 子 量 】241.28964 【元素组成】C 74.67% H 6.27% N 5.8% O 13.26% |
合成路线1
该中间体在本合成路线中的序号：(VII)7-Aminoquinolin-2-one (III) was prepared by Knorr cyclization of m-phenylenediamine (I) with ethyl acetoacetate (II). Subsequent diazotization of (II), followed by acid hydrolysis gave rise to the 7-hydroxyquinolinone (IV). Alkylation of (IV) with 3-chloro-3-methylbut-1-yne (V), followed by Claisen rearrangement of the resulting propargyl ether (V) afforded the pyranoquinolinone (VII). This was protected as the N-Boc derivative (VIII) by treatment with Boc2O and Et3N. Sharpless asymmetric dihydroxylation of (VIII) using dihydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether ((DHQ)2-PYR) as the chiral catalyst furnished the (R,R)-diol (IX), which was esterified with (-)-(S)-camphanoyl chloride (X) to produce diester (XI). The Boc protecting group of (XI) was finally removed by treatment with trifluoroacetic acid.
| 【1】 Cosentino, L.M.; Xia, Y.; Yang, Z.-Y.; Brossi, A.; Lee, K.-H.; Anti-AIDS agents Part 41: Synthesis and anti-HIV activity of 3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (DCK) lactam analogues. Bioorg Med Chem Lett 2000, 10, 10, 1003. |
| 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) | 41612 | 1,3-benzenediamine; 3-aminophenylamine | 108-45-2 | C6H8N2 | 详情 | 详情 |
| (II) | 11819 | ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate | 141-97-9 | C6H10O3 | 详情 | 详情 |
| (III) | 41613 | 7-amino-4-methyl-2(1H)-quinolinone | 19840-99-4 | C10H10N2O | 详情 | 详情 |
| (IV) | 41614 | 7-hydroxy-4-methyl-2(1H)-quinolinone | C10H9NO2 | 详情 | 详情 | |
| (V) | 22416 | 3-chloro-3-methyl-1-butyne | 1111-97-3 | C5H7Cl | 详情 | 详情 |
| (VI) | 41615 | 7-[(1,1-dimethyl-2-propynyl)oxy]-4-methyl-2(1H)-quinolinone | C15H15NO2 | 详情 | 详情 | |
| (VII) | 41616 | 4,8,8-trimethyl-1,8-dihydro-2H-pyrano[2,3-h]quinolin-2-one | C15H15NO2 | 详情 | 详情 | |
| (VIII) | 41617 | tert-butyl 4,8,8-trimethyl-2-oxo-2H-pyrano[2,3-h]quinoline-1(8H)-carboxylate | C20H23NO4 | 详情 | 详情 | |
| (IX) | 41618 | tert-butyl (9R,10R)-9,10-dihydroxy-4,8,8-trimethyl-2-oxo-9,10-dihydro-2H-pyrano[2,3-h]quinoline-1(8H)-carboxylate | C20H25NO6 | 详情 | 详情 | |
| (X) | 41620 | (1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride | C10H13ClO3 | 详情 | 详情 | |
| (XI) | 41619 | tert-butyl (9R,10R)-4,8,8-trimethyl-2-oxo-9,10-bis([[(4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]hept-1-yl]carbonyl]oxy)-9,10-dihydro-2H-pyrano[2,3-h]quinoline-1(8H)-carboxylate | C40H49NO12 | 详情 | 详情 |