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【结 构 式】 
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【药物名称】SL-3111 【化学名称】4-Benzyl-1-(4-tert-butyl-3'-hydroxybenzhydryl)piperazine dihydrochloride 【CA登记号】219505-08-5 (free base) 【 分 子 式 】C28H36Cl2N2O 【 分 子 量 】487.51792 |
【开发单位】University of Arizona (Originator) 【药理作用】Pharmacological Tools, delta-Opioid Agonists |
合成路线1
Protection of 3-hydroxybenzaldehyde (I) with methoxymethyl chloride afforded the corresponding methoxymethyl ether (II). Subsequent addition of 4-tert-butylphenylmagnesium bromide (III) produced the diarylcarbinol (IV), which was converted to chloride (V) by means of CCl4 and PPh3. Condensation of (V) with 1-benzylpiperazine (VI) yielded the disubstituted piperazine (VII). The methoxymethyl ether of (VII) was finally deprotected with aqueous HCl to provide the title compound.
| 【1】 Liao, S.; Alfaro-Lopez, J.; Shenderovich, M.D.; Hosohata, K.; Lin, J.; Li, X.; Stropova, D.; Davis, P.; Jernigan, K.A.; Porreca, F.; Yamamura, H.I.; Hruby, V.J.; De novo design, synthesis, and biological activities of high-affinity and selective non-peptide agonists of the delta-opioid receptor. J Med Chem 1998, 41, 24, 4767. |
| 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) | 28537 | 3-hydroxybenzaldehyde | 100-83-4 | C7H6O2 | 详情 | 详情 |
| (II) | 28538 | 3-(methoxymethoxy)benzaldehyde | C9H10O3 | 详情 | 详情 | |
| (III) | 28539 | bromo[4-(tert-butyl)phenyl]magnesium | C10H13BrMg | 详情 | 详情 | |
| (IV) | 28540 | [4-(tert-butyl)phenyl][3-(methoxymethoxy)phenyl]methanol | C19H24O3 | 详情 | 详情 | |
| (V) | 28541 | 1-[[4-(tert-butyl)phenyl](chloro)methyl]-3-(methoxymethoxy)benzene | C19H23ClO2 | 详情 | 详情 | |
| (VI) | 28542 | N-Benzylpiperazine; 1-Benzylpiperazine | 2759-28-6 | C11H16N2 | 详情 | 详情 |
| (VII) | 28543 | (3-[(4-benzyl-1-piperazinyl)[4-(tert-butyl)phenyl]methyl]phenoxy)methyl methyl ether | C30H38N2O2 | 详情 | 详情 |
Extended Information