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【结 构 式】 
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【分子编号】28081 【品名】benzyl 18-(4-iodophenyl)octadecyl ether 【CA登记号】 |
【 分 子 式 】C31H47IO 【 分 子 量 】562.61805 【元素组成】C 66.18% H 8.42% I 22.56% O 2.84% |
合成路线1
该中间体在本合成路线中的序号：(VI)Iodophenylpentadecanoic acid (I) was reduced to the corresponding alcohol (II) with borane in THF and then converted to the tosylate (III). Treatment of 3-(benzyloxy)propanol (IV) with CBr4 and PPh3 afforded bromide (V). This was treated with Mg in THF and the resulting Grignard reagent was coupled with tosylate (III) in the presence of Li2CuCl4 to provide octadecyl benzyl ether (VI), which was cleaved to the aryl octadecanol (VII) using AlCl3 and anisole. Reaction of alcohol (VII) with phospholane (VIII), followed by condensation with trimethylamine then furnished the title compound.
| 【1】 Weichert, J.P.; Rampy, M.A.; Counsell, R.E.; Longino, M.A.; Pinchuk, A.N. (University of Michigan); Radioiodinated phospholipid ether analogs and methods of using the same. WO 9824480 . |
| 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) | 28077 | 15-(4-iodophenyl)pentadecanoic acid | C21H33IO2 | 详情 | 详情 | |
| (II) | 28078 | 15-(4-iodophenyl)-1-pentadecanol | C21H35IO | 详情 | 详情 | |
| (III) | 28079 | 15-(4-iodophenyl)pentadecyl 4-methylbenzenesulfonate | C28H41IO3S | 详情 | 详情 | |
| (IV) | 14687 | 3-(benzyloxy)-1-propanol; 3-(Benzyloxy)propanol | 4799-68-2 | C10H14O2 | 详情 | 详情 |
| (V) | 28080 | 1-[(3-bromopropoxy)methyl]benzene | C10H13BrO | 详情 | 详情 | |
| (VI) | 28081 | benzyl 18-(4-iodophenyl)octadecyl ether | C31H47IO | 详情 | 详情 | |
| (VII) | 28081 | benzyl 18-(4-iodophenyl)octadecyl ether | C31H47IO | 详情 | 详情 | |
| (VIII) | 28082 | 18-(4-iodophenyl)-1-octadecanol | C24H41IO | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VII)Iodophenylpentadecanoic acid (I) was reduced to the corresponding alcohol (II) with borane in THF and then converted to the tosylate (III). Treatment of 3-(benzyloxy)propanol (IV) with CBr4 and PPh3 afforded bromide (V). This was treated with Mg in THF and the resulting Grignard reagent was coupled with tosylate (III) in the presence of Li2CuCl4 to provide octadecyl benzyl ether (VI), which was cleaved to the aryl octadecanol (VII) using AlCl3 and anisole. Reaction of alcohol (VII) with phospholane (VIII), followed by condensation with trimethylamine then furnished the title compound.
| 【1】 Weichert, J.P.; Rampy, M.A.; Counsell, R.E.; Longino, M.A.; Pinchuk, A.N. (University of Michigan); Radioiodinated phospholipid ether analogs and methods of using the same. WO 9824480 . |
| 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) | 28077 | 15-(4-iodophenyl)pentadecanoic acid | C21H33IO2 | 详情 | 详情 | |
| (II) | 28078 | 15-(4-iodophenyl)-1-pentadecanol | C21H35IO | 详情 | 详情 | |
| (III) | 28079 | 15-(4-iodophenyl)pentadecyl 4-methylbenzenesulfonate | C28H41IO3S | 详情 | 详情 | |
| (IV) | 14687 | 3-(benzyloxy)-1-propanol; 3-(Benzyloxy)propanol | 4799-68-2 | C10H14O2 | 详情 | 详情 |
| (V) | 28080 | 1-[(3-bromopropoxy)methyl]benzene | C10H13BrO | 详情 | 详情 | |
| (VI) | 28081 | benzyl 18-(4-iodophenyl)octadecyl ether | C31H47IO | 详情 | 详情 | |
| (VII) | 28081 | benzyl 18-(4-iodophenyl)octadecyl ether | C31H47IO | 详情 | 详情 | |
| (VIII) | 28082 | 18-(4-iodophenyl)-1-octadecanol | C24H41IO | 详情 | 详情 |