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【结 构 式】 
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【分子编号】51424 【品名】[(1R,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl pivalate 【CA登记号】 |
【 分 子 式 】C15H24O2 【 分 子 量 】236.35436 【元素组成】C 76.23% H 10.23% O 13.54% |
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：(XVII)The intermediate 4-hydroxy-myrtenyl pivalate (XIII) has been obtained as follows: The reaction of (1R,5S)-myrtenol (XV) with pivaloyl chloride (XVI) and pyridine in dichloromethane gives the pivalate ester (XVII), which by an allylic oxidation with CrO3 and 3,5-dimethylpyrazole in dichloromethane yields 4-oxo-myrtenyl pivalate (XVIII). Finally, this compound is reduced with LiAlH(OBu)3 in THF to afford the target 4-hydroxy-myrtenyl pivalate (XIII) intermediate.
| 【1】 Huffman, J.W.; Liddle, J.; Enantioselective synthesis of 11-hydroxy-(1'S,2'R)-dimethylheptyl-DELTA8-THC, a very potent CB1 agonist. Tetrahedron 2001, 57, 36, 7607. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIII) | 24407 | [(1R,5S)-4-hydroxy-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl pivalate | C15H24O3 | 详情 | 详情 | |
| (XV) | 51423 | [(1R,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol | C10H16O | 详情 | 详情 | |
| (XVI) | 13597 | 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride | 3282-30-2 | C5H9ClO | 详情 | 详情 |
| (XVII) | 51424 | [(1R,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl pivalate | C15H24O2 | 详情 | 详情 | |
| (XVIII) | 51425 | [(1R,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]hept-2-en-2-yl]methyl pivalate | C15H22O3 | 详情 | 详情 |
Extended Information