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【结 构 式】 
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【分子编号】44847 【品名】1-ethynyl-4-methoxybenzene; 4-ethynylphenyl methyl ether 【CA登记号】 |
【 分 子 式 】C9H8O 【 分 子 量 】132.16192 【元素组成】C 81.79% H 6.1% O 12.11% |
合成路线1
该中间体在本合成路线中的序号：(I)Reaction of 4-ethynylanisole (I) with nido-decaborane (II) in acetonitrile/benzene affords compound (III), which is then converted into (V) by reaction with BuLi in DME followed by treatment with CuCl and condensation with 2-(11-bromo-n-undecyloxy)tetrahydro-2H-pyran (IV) in pyridine. Removal of the THP group with p-toluenesulfonic acid in MeOH gives alcohol (VI), which is oxidized with CrO3 and H2SO4 in acetone to provide carboxylic acid (VIII) and ester (VII). Ester (VII) is then converted into carboxylic acid (VIII) by hydrolysis with H2SO4 in dioxane/H2O, which is demethylated with BBr3 in CH2Cl2. Finally, the resulting compound is coupled with butylamine (IX) by means of DCC in acetonitrile.
| 【1】 Endo, Y.; et al.; New estrogenic antagonists bearing dicarba-closo-dodecaborane as a hydrophobic pharmacophore. Chem Pharm Bull 2000, 48, 2, 312. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 44847 | 1-ethynyl-4-methoxybenzene; 4-ethynylphenyl methyl ether | C9H8O | 详情 | 详情 | |
| (II) | 44848 | decaborane | H14B10 | 详情 | 详情 | |
| (III) | 44849 | methyl 4-[2-[6-(1-triboriranyl)hexaboranyl]-2-boriranyl]phenyl ether; 1-[6-[2-(4-methoxyphenyl)-2-boriranyl]hexaboranyl]triborirane | C9H18B10O | 详情 | 详情 | |
| (IV) | 44850 | 11-(1lambda(3)-dibromanyl)undecyl tetrahydro-2H-pyran-2-yl ether; 2-[[11-(1lambda(3)-dibromanyl)undecyl]oxy]tetrahydro-2H-pyran | C16H32Br2O2 | 详情 | 详情 | |
| (V) | 44851 | 12-[3-(4-methoxyphenyl)-3-[6-(1-triboriranyl)hexaboranyl]-2-boriranyl]dodecyl tetrahydro-2H-pyran-2-yl ether; 1-[2-(4-methoxyphenyl)-3-[12-(tetrahydro-2H-pyran-2-yloxy)dodecyl]-2-boriranyl]-6-(1-triboriranyl)hexaborane | C26H50B10O3 | 详情 | 详情 | |
| (VI) | 44852 | 11-[3-(4-methoxyphenyl)-3-[6-(1-triboriranyl)hexaboranyl]-2-boriranyl]-1-undecanol | C20H40B10O2 | 详情 | 详情 | |
| (VII) | 44853 | 3-(4-methoxyphenyl)-3-[6-(1-triboriranyl)hexaboranyl]-2-boriranyl 11-[3-(4-methoxyphenyl)-3-[6-(1-triboriranyl)hexaboranyl]-2-boriranyl]undecanoate | C29H54B20O4 | 详情 | 详情 | |
| (VIII) | 44854 | 11-[3-(4-methoxyphenyl)-3-[6-(1-triboriranyl)hexaboranyl]-2-boriranyl]undecanoic acid | C20H38B10O3 | 详情 | 详情 | |
| (IX) | 39041 | butylamine; 1-butanamine | 109-73-9 | C4H11N | 详情 | 详情 |