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【结 构 式】 
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【分子编号】43525 【品名】methyl (E)-2-[2-[(dimethoxyphosphoryl)methyl]phenyl]-3-methoxy-2-propenoate 【CA登记号】 |
【 分 子 式 】C14H19O6P 【 分 子 量 】314.275022 【元素组成】C 53.51% H 6.09% O 30.55% P 9.86% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(III)Bromination of acrylate derivative (I) by means of NBS and AIBN in CCl4 affords (II), which is then converted into (III) by reaction with trimethyl phosphite (A) in toluene. Wittig oxopropenylation of aldehyde (IV) with phosphonium bromide derivative (V) and NaOMe or NaOEt in DMF provides benzaldehyde derivative (VI), which finally reacts with phosphonate (III) and NaH by a Wittig-Horner reaction in THF.
| 【1】 McCoy, R.K.; Spangler, C.W.; Preparation of conjugated aromatic polyenals by witting oxopropenylation. Synth Commun 1988, 18, 1, 51. |
| 【2】 Alzeer, J.; Chollet, J.; Matile, H.; Ridley, R.G.; Hubschwerlen, C.; Heinze-Krauss, I.; Phenyl beta-methoxyacrylates: A new antimalarial pharmacophore. J Med Chem 2000, 43, 4, 560. |
| 【3】 Matile, H.; Chollet, J.; Alzeer, J.; Ridley, R.G.; Hubschwerlen, C. (F. Hoffmann-La Roche AG); beta-Alkoxyacrylates against malaria. EP 0996439; WO 9902150 . |
| 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) | 12642 | Trimethyl phosphite | 121-45-9 | C3H9O3P | 详情 | 详情 |
| (I) | 43523 | methyl (E)-3-methoxy-2-(2-methylphenyl)-2-propenoate | C12H14O3 | 详情 | 详情 | |
| (II) | 43524 | methyl (E)-2-[2-(bromomethyl)phenyl]-3-methoxy-2-propenoate | C12H13BrO3 | 详情 | 详情 | |
| (III) | 43525 | methyl (E)-2-[2-[(dimethoxyphosphoryl)methyl]phenyl]-3-methoxy-2-propenoate | C14H19O6P | 详情 | 详情 | |
| (IV) | 22196 | 2,4-dichlorobenzaldehyde | 874-42-0 | C7H4Cl2O | 详情 | 详情 |
| (V) | 43526 | tributyl(1,3-dioxolan-2-ylmethyl)phosphonium bromide | C16H34BrO2P | 详情 | 详情 | |
| (VI) | 43527 | (E)-3-(2,4-dichlorophenyl)-2-propenal | C9H6Cl2O | 详情 | 详情 |
Extended Information