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【结 构 式】 
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【分子编号】18228 【品名】2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]aniline; 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenylamine 【CA登记号】 |
【 分 子 式 】C18H21NO4 【 分 子 量 】315.36908 【元素组成】C 68.55% H 6.71% N 4.44% O 20.29% |
合成路线1
该中间体在本合成路线中的序号：(V)Wittig reaction of 3,4,5-trimethoxybenzyl phosphonium bromide (I) with benzaldehyde (II) in the presence of NaH in toluene yielded a 1:1 mixture of E (III) and Z (IV) stilbenes, from which the Z isomer was separated by crystallization from EtOAc and then from EtOH. Then, nitro group of (IV) was reduced with Zn in AcOH at room temperature to give anilino compound (V), which was converted to the hydrochloride salt with HCl in dioxane-methylene chloride.
| 【1】 Suga, Y.; Ohsumi, K.; Fukuda, Y.; Nihei, Y.; Hatanaka, T.; Tsuji, T.; Nakagawa, R.; Morrinaga, Y.; Ohishi, K.; Akiyama, Y.; Novel combretastatin analogue effective against murine solid tumors: Design and structure-activity relationships. J Med Chem 1998, 41, 16, 3022. |
| 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) | 18224 | triphenyl(3,4,5-trimethoxybenzyl)phosphorane; 2,3-dimethoxy-5-[(triphenylphosphoranyl)methyl]phenyl methyl ether | C28H29O3P | 详情 | 详情 | |
| (II) | 18225 | 4-METHOXY-3-NITROBENZALDEHYDE | 31680-08-7 | C8H7NO4 | 详情 | 详情 |
| (III) | 18226 | 2,3-dimethoxy-5-[(E)-2-(4-methoxy-3-nitrophenyl)ethenyl]phenyl methyl ether; 1,2,3-trimethoxy-5-[(E)-2-(4-methoxy-3-nitrophenyl)ethenyl]benzene | C18H19NO6 | 详情 | 详情 | |
| (IV) | 28720 | 2,3-dimethoxy-5-[(Z)-2-(4-methoxy-3-nitrophenyl)ethenyl]phenyl methyl ether; 1,2,3-trimethoxy-5-[(Z)-2-(4-methoxy-3-nitrophenyl)ethenyl]benzene | C18H19NO6 | 详情 | 详情 | |
| (V) | 18228 | 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]aniline; 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenylamine | C18H21NO4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)Coupling of (Z)-1-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)- ethene (I) with N-Fmoc-O-acetyl-L-serine (II) in the presence of DCC and HOBt provided the corresponding serineamide (III). Further deprotection of Fmoc and acetyl groups with NaOH furnished the title compound.
| 【1】 Hatanaka, T.; Ohsumi, K.; Tsuji, T.; Nihei, Y.; Nakagawa, R.; Ohishi, K. (Ajinomoto Co., Inc.); Stilbene derivs. and pharmaceutical compsns. containing them. CA 2171275; EP 0731085; JP 1996301831; US 5674906 . |
| 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) | 18228 | 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]aniline; 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenylamine | C18H21NO4 | 详情 | 详情 | |
| (II) | 25685 | (2S)-3-(acetoxy)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propionic acid | C20H19NO6 | 详情 | 详情 | |
| (III) | 25686 | 9H-fluoren-9-ylmethyl (1S)-1-[(isopropenyloxy)methyl]-2-[2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]anilino]-2-oxoethylcarbamate | C39H40N2O8 | 详情 | 详情 |