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【结 构 式】 
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【分子编号】51685 【品名】4-[2-(10H-phenoxazin-10-yl)ethoxy]benzaldehyde 【CA登记号】 |
【 分 子 式 】C21H17NO3 【 分 子 量 】331.37092 【元素组成】C 76.12% H 5.17% N 4.23% O 14.48% |
合成路线1
该中间体在本合成路线中的序号：(XV)In a related method, 4-(2-bromoethoxy)benzaldehyde (XI) was subjected to a Horner-Emmons reaction with phosphonate (II) to produce the unsaturated ester (XIIa-b), which was further hydrogenated to afford (XIII). Alkylation of phenoxazine (XIV) with bromide (XIII) gave adduct (VIII) (1,2). In a different reaction sequence, bromoaldehyde (XI) was initially condensed with phenoxazine (XIV), producing adduct (XV). This was subjected to Horner-Emmons condensation with (II) to give the unsaturated ester (XVIa-b), which was then hydrogenated to (VIII). Alternatively, double-bond reduction of (XVI) by means of Mg in MeOH gave rise to the transesterified methyl ester (IX). Ester hydrolysis as above provided acid (X).
| 【2】 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 . |
| 【3】 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 . |
| 【1】 Lohray, B.B.; et al.; (-)-3-[4-[2-(Phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoic acid[(-)DRF 2725]: A dual PPAR agonist with potent antihyperglycemic and lipid modulating activity. J Med Chem 2001, 44, 16, 2675. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIIa) | 51686 | ethyl (E)-3-[4-(2-bromoethoxy)phenyl]-2-ethoxy-2-propenoate | C15H19BrO4 | 详情 | 详情 | |
| (XIIb) | 51687 | ethyl (Z)-3-[4-(2-bromoethoxy)phenyl]-2-ethoxy-2-propenoate | C15H19BrO4 | 详情 | 详情 | |
| (XVIa) | 51689 | ethyl (E)-2-ethoxy-3-[4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl]-2-propenoate | C27H27NO5 | 详情 | 详情 | |
| (XVba) | 51690 | ethyl (Z)-2-ethoxy-3-[4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl]-2-propenoate | C27H27NO5 | 详情 | 详情 | |
| (II) | 51675 | ethyl 2-(diethoxyphosphoryl)-2-ethoxyacetate | C10H21O6P | 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 | |
| (XI) | 18799 | 4-(2-bromoethoxy)benzaldehyde | 52191-15-8 | C9H9BrO2 | 详情 | 详情 |
| (XIII) | 51688 | ethyl 3-[4-(2-bromoethoxy)phenyl]-2-ethoxypropanoate | C15H21BrO4 | 详情 | 详情 | |
| (XIV) | 51684 | 2,3,5,6-Dibenzo-1,4-oxazine; Phenoxazine | 135-67-1 | C12H9NO | 详情 | 详情 |
| (XV) | 51685 | 4-[2-(10H-phenoxazin-10-yl)ethoxy]benzaldehyde | C21H17NO3 | 详情 | 详情 |