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【结 构 式】 
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【分子编号】36009 【品名】1-[(1S,2R)-1-ethyl-2-(3-methoxyphenyl)butyl]-3-methoxybenzene; 3-[(1R,2S)-1-ethyl-2-(3-methoxyphenyl)butyl]phenyl methyl ether 【CA登记号】 |
【 分 子 式 】C20H26O2 【 分 子 量 】298.42524 【元素组成】C 80.5% H 8.78% O 10.72% |
合成路线1
该中间体在本合成路线中的序号：(IIIa)The synthesis of 3,4-bis(3'-methoxyphenyl)hexane (III) was accomplished in two different ways: 1) Reductive coupling of the 3-methoxypropiophenone (I) using the TiCl4/Zn reaction -- introduced by Mukaiyama et al. -- yields preferably the cis-stilbene (II). Catalytic hydrogenation of this alkene using palladium on activated carbon results in the isomerically pure meso-3,4-bis(3'-methoxyphenyl)hexane (III). 2) The reductive coupling of the 1-(3'-methoxyphenyl)-1-chloropropane (VI), obtained from 1-(3-methoxyphenyl)propanol (V) with dry HCl, according to Wilds and McCormack using COCl2 and ethylmagnesium bromide (A) yields mixture of the meso- and di-3,4-bis(3'-methoxyphenyl)hexanes (III). The meso-diastereomer (III) is separated by fractional crystallization from methanol. The ether cleavage of (III) to give 3,4-bis(3'-hydroxyphenyl)hexane is accomplished with BBr3.
| 【1】 Hitova, M.; Kouzeva, V.; J Org Chem 1949, 14, Suppl. 1, 45-58. |
| 【2】 Resende, C.; Barros, L.; Mota, A.; Barros, M.A.; Veloso, T.; Mesquita-Guimaraes, J.; Cunha, A.P.; J Cancer Res Clin Oncol 1982, 103, Suppl. 1, 165-180. |
| 【3】 El-Ashmawi, N.; Abdel-Samad, Z.; Sallam, F.; Nassar, S.; Gamae, M.; Chem Lett 1973, 16, Suppl. 1, 1041-44. |
| 【4】 Schonenberger, H.; Kranfelder, G.; Schmitt-Wallenborn, H. (Klinge Pharma GmbH); Novel di-(3'-hydroxyphenyl)-alkane cpds., process of preparation and their use in medicine. DE 2658307; US 4094994 . |
| 【5】 Schonenberger, H.; Engel, J.; Hartmann, R.W.; Metahexestrol. Drugs Fut 1983, 8, 5, 413. |
| 【6】 Picq, M.; et al.; Pentasubstituted quercetin analogues as selective inhibitors of particulate 3':5'-cyclic-AMP phosphodiesterase from rat brain. J Med Chem 1982, 24, 10, 1192-97. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 24239 | bromo(ethyl)magnesium；ethylmagnesium bromide | 925-90-6 | C2H5BrMg | 详情 | 详情 |
| (IIIa) | 36009 | 1-[(1S,2R)-1-ethyl-2-(3-methoxyphenyl)butyl]-3-methoxybenzene; 3-[(1R,2S)-1-ethyl-2-(3-methoxyphenyl)butyl]phenyl methyl ether | C20H26O2 | 详情 | 详情 | |
| (IIIb) | 36010 | 3-[(1S,2S)-1-ethyl-2-(3-methoxyphenyl)butyl]phenyl methyl ether; 1-[(1S,2S)-1-ethyl-2-(3-methoxyphenyl)butyl]-3-methoxybenzene | C20H26O2 | 详情 | 详情 | |
| (I) | 36007 | 1-(3-methoxyphenyl)-1-propanone | C10H12O2 | 详情 | 详情 | |
| (II) | 36008 | 1-[(Z)-1-ethyl-2-(3-methoxyphenyl)-1-butenyl]-3-methoxybenzene; 3-[(Z)-1-ethyl-2-(3-methoxyphenyl)-1-butenyl]phenyl methyl ether | C20H24O2 | 详情 | 详情 | |
| (V) | 36012 | 1-(3-methoxyphenyl)-1-propanol | C10H14O2 | 详情 | 详情 | |
| (VI) | 36011 | 3-(1-chloropropyl)phenyl methyl ether; 1-(1-chloropropyl)-3-methoxybenzene | C10H13ClO | 详情 | 详情 |