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【结 构 式】 
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【分子编号】18189 【品名】1-isopropyl-1,2,3,4-tetrahydro-6-quinolinecarbaldehyde 【CA登记号】 |
【 分 子 式 】C13H17NO 【 分 子 量 】203.28412 【元素组成】C 76.81% H 8.43% N 6.89% O 7.87% |
合成路线1
该中间体在本合成路线中的序号：(II)Formylation of tetrahydroquinoline (I) with N,N-dimethylformamide and POCl3 afforded aldehyde (II), which was condensed with ethylmagnesium bromide to give alcohol (III), and then oxidized to ketone (IV) with activated MnO2 in acetone. Coupling with triethyl 2-fluoro-2-phosphonoacetate (V) in the presence of NaH in DMF produced a mixture of olefins, from which the desired E isomer (VI) was separated by column chromatography. Ester reduction with DIBAL-H at -70 C provided the E-alcohol (VII), which was oxidized to aldehyde (VIII) with MnO2 in acetone. Horner-Emmons condensation with phosphonate (IX) afforded heptatrienoic ester (X), which was finally hydrolyzed with NaOH to the target heptatrienoic acid.
| 【1】 Hibi, S.; Kikuchi, K.; Yoshimura, H.; Nagai, M.; Tai, K.; Hida, T.; Syntheses and structure-activity relationships of novel retinoid X receptor agonists. J Med Chem 1998, 41, 17, 3245. |
| 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) | 18188 | 1-isopropyl-1,2,3,4-tetrahydroquinoline | C12H17N | 详情 | 详情 | |
| (II) | 18189 | 1-isopropyl-1,2,3,4-tetrahydro-6-quinolinecarbaldehyde | C13H17NO | 详情 | 详情 | |
| (III) | 18190 | 1-(1-isopropyl-1,2,3,4-tetrahydro-6-quinolinyl)-1-propanol | C15H23NO | 详情 | 详情 | |
| (IV) | 18191 | 1-(1-isopropyl-1,2,3,4-tetrahydro-6-quinolinyl)-1-propanone | C15H21NO | 详情 | 详情 | |
| (V) | 18192 | ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate | 2356-16-3 | C8H16FO5P | 详情 | 详情 |
| (VI) | 18193 | ethyl (E)-2-fluoro-3-(1-isopropyl-1,2,3,4-tetrahydro-6-quinolinyl)-2-pentenoate | C19H26FNO2 | 详情 | 详情 | |
| (VII) | 18194 | (E)-2-fluoro-3-(1-isopropyl-1,2,3,4-tetrahydro-6-quinolinyl)-2-penten-1-ol | C17H24FNO | 详情 | 详情 | |
| (VIII) | 18195 | (E)-2-fluoro-3-(1-isopropyl-1,2,3,4-tetrahydro-6-quinolinyl)-2-pentenal | C17H22FNO | 详情 | 详情 | |
| (IX) | 18196 | methyl (E)-4-(diethoxyphosphoryl)-3-methyl-2-butenoate | C10H19O5P | 详情 | 详情 | |
| (X) | 18197 | methyl (2E,4E,6E)-6-fluoro-7-(1-isopropyl-1,2,3,4-tetrahydro-6-quinolinyl)-3-methyl-2,4,6-nonatrienoate | C23H30FNO2 | 详情 | 详情 |