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【结 构 式】 
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【分子编号】28185 【品名】6-chloro-3-oxo-2-oxabicyclo[3.2.1]octane-8-carbonyl chloride 【CA登记号】 |
【 分 子 式 】C8H8Cl2O3 【 分 子 量 】223.05512 【元素组成】C 43.08% H 3.62% Cl 31.79% O 21.52% |
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：(V)Synthesis of intermediate (VIII). The hydrochloration of 5-oxotricyclo[2.2.1.0~2,6~]heptane-3-carboxylic acid (II) gives 2-chloro-5-oxobicyclo[2.2.1]heptane-7-carboxylic acid (III), which is treated with peracetic acid yielding lactone (IV). This compound is treated with SOCl2 to obtain acyl chloride (V), which is converted into aldehyde (VI) by means H2 over Pd. The Horner-Emmons-Wiittig reaction of aldehyde (VI) and phosphonate (VII) by means NaH affords intermediate (VIII).
| 【1】 Peel, R.; Sutherland, J.K.; Beeley, N.R.A.; Tetrahedron 1981, 37, 411. |
| 【2】 Jahne, G.; Wess, G.; Bartmann, W.; Beck, G.; Lerch, U.; Liebigs Ann Chem 1987, 321-326. |
| 【3】 Beck, G.; Dimoxaprost. Drugs Fut 1987, 12, 12, 1101. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 28182 | 5-oxotricyclo[2.2.1.0(2,6)]heptane-3-carboxylic acid | 70748-53-7 | C8H8O3 | 详情 | 详情 |
| (III) | 28183 | 2-chloro-5-oxobicyclo[2.2.1]heptane-7-carboxylic acid | 52730-42-4 | C8H9ClO3 | 详情 | 详情 |
| (IV) | 28184 | 6-chloro-3-oxo-2-oxabicyclo[3.2.1]octane-8-carboxylic acid | C8H9ClO4 | 详情 | 详情 | |
| (V) | 28185 | 6-chloro-3-oxo-2-oxabicyclo[3.2.1]octane-8-carbonyl chloride | C8H8Cl2O3 | 详情 | 详情 | |
| (VI) | 28186 | 6-chloro-3-oxo-2-oxabicyclo[3.2.1]octane-8-carbaldehyde | C8H9ClO3 | 详情 | 详情 | |
| (VII) | 28187 | dimethyl 4-ethoxy-3,3-dimethyl-2-oxobutylphosphonate | C10H21O5P | 详情 | 详情 | |
| (VIII) | 28188 | 6-chloro-8-[(E)-5-ethoxy-4,4-dimethyl-3-oxo-1-pentenyl]-2-oxabicyclo[3.2.1]octan-3-one | C16H23ClO4 | 详情 | 详情 |
Extended Information