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【结 构 式】 
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【分子编号】51682 【品名】ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate 【CA登记号】 |
【 分 子 式 】C13H18O4 【 分 子 量 】238.28352 【元素组成】C 65.53% H 7.61% O 26.86% |
合成路线1
该中间体在本合成路线中的序号：(IV)Several related procedures have been described for the synthesis of the title compound. The Horner-Emmons reaction of 4-benzyloxybenzaldehyde (I) with triethyl 2-ethoxyphosphonoacetate (II) afforded the unsaturated ester (IIIa-b) as a mixture of E/Z isomers. Simultaneous double-bond hydrogenation and benzyl group hydrogenolysis in the presence of Pd/C furnished phenol (IV). Alternatively, double-bond reduction by means of magnesium in MeOH was accompanied by transesterification, yielding the saturated methyl ester (V). Further benzyl group hydrogenolysis of (V) over Pd/C gave phenol (VI). The alkylation of phenols (IV) and (VI) with the phenoxazinylethyl mesylate (VII) provided the corresponding ethers (VIII) and (IX), respectively. The racemic carboxylic acid (X) was then obtained by hydrolysis of either ethyl- (VIII) or methyl- (IX) esters under basic conditions.
| 【1】 Kalchar, S.; Lohray, V.B.; Lohray, B.B.; Chakrabarti, R.; Bajji, A.C.; Ramanujam, R. (Dr. Reddy's Research Foundation); Novel tricyclic cpds. and their use in medicine; process for their preparation and pharmaceutical compsns. containing them. EP 1049684; JP 2001519422; WO 9919313 . |
| 【2】 Rajagopalan, R.; Ashok, C.B.; Shivaramayya, K.; Gurram, R.M.; Lohray, B.B.; Paraselli, B.R.; Rajan, C.; Lohray, V.B. (Dr. Reddy's Research Foundation); Novel tricyclic cpds. and their use in medicine; process for their preparation and pharmaceutical compsn. containing them. EP 1155006; WO 0050414 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IIIa) | 50411 | ethyl (E)-3-[4-(benzyloxy)phenyl]-2-ethoxy-2-propenoate | C20H22O4 | 详情 | 详情 | |
| (IIIb) | 51683 | ethyl (Z)-3-[4-(benzyloxy)phenyl]-2-ethoxy-2-propenoate | C20H22O4 | 详情 | 详情 | |
| (I) | 29179 | 4-(Benzyloxy)benzaldehyde | 4397-53-9 | C14H12O2 | 详情 | 详情 |
| (II) | 51675 | ethyl 2-(diethoxyphosphoryl)-2-ethoxyacetate | C10H21O6P | 详情 | 详情 | |
| (IV) | 51682 | ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate | C13H18O4 | 详情 | 详情 | |
| (V) | 51676 | methyl 3-[4-(benzyloxy)phenyl]-2-ethoxypropanoate | C19H22O4 | 详情 | 详情 | |
| (VI) | 51677 | methyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate | C12H16O4 | 详情 | 详情 | |
| (VII) | 51678 | 2-(10H-phenoxazin-10-yl)ethyl methanesulfonate | C15H15NO4S | 详情 | 详情 | |
| (VIII) | 51679 | ethyl 2-ethoxy-3-[4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl]propanoate | C27H29NO5 | 详情 | 详情 | |
| (IX) | 51680 | methyl 2-ethoxy-3-[4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl]propanoate | C26H27NO5 | 详情 | 详情 | |
| (X) | 51681 | 2-ethoxy-3-[4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl]propionic acid | C25H25NO5 | 详情 | 详情 |