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【结 构 式】 
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【分子编号】53371 【品名】2-Bromo-9-fluorenone 【CA登记号】3096-56-8 |
【 分 子 式 】C13H7BrO 【 分 子 量 】259.10198 【元素组成】C 60.26% H 2.72% Br 30.84% O 6.17% |
合成路线1
该中间体在本合成路线中的序号：(VII)Alkylation of the lithium salt of 2-(3,4-dimethoxyphenyl)isobutyronitrile (I) with 1,3-dibromopropane (II) gave the bromo nitrile (III). Conversion of bromide (III) into the desired primary amine (VI) was achieved through a Gabriel synthesis by condensation with potassium phthalimide (IV), followed by hydrazinolysis of the resultant N-substituted phthalimide (V). A two-step procedure was finally employed for the reductive alkylation of amine (VI), consisting of condensation between amine (VI) and the bromo fluorenone (VII) in the presence of titanium isopropoxide and then reduction of the intermediate (VIII) with NaBH3CN.
| 【1】 Dei, S.; et al.; Structure-activity relationships and optimisation of the selective MDR modulator 2-(3,4-dimethoxyphenyl)-5-(9-fluorenylamino)-2-(methylethyl) pentanenitrile and its N-methyl derivative. Bioorg Med Chem 2001, 9, 10, 2673. |
| 【2】 Teodori, E.; Dei, S.; Quidu, P.; et al.; Design, synthesis, and in vitro activity of catamphiphilic reverters of multidrug resistance: Discovery of a selective, highly efficacious chemosensitizer with potency in the nanomolar range. J Med Chem 1999, 42, 10, 1687. |
| 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) | 30391 | 2-(3,4-dimethoxyphenyl)-3-methylbutanenitrile; alpha-Isopropylveratryl cyanide | 20850-49-1 | C13H17NO2 | 详情 | 详情 |
| (II) | 12581 | 1,3-Dibromopropane | 109-64-8 | C3H6Br2 | 详情 | 详情 |
| (III) | 30392 | 5-bromo-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile | C16H22BrNO2 | 详情 | 详情 | |
| (IV) | 27890 | Potassium phthalimide | 1074-82-4 | C8H4KNO2 | 详情 | 详情 |
| (V) | 53369 | 2-(3,4-dimethoxyphenyl)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-isopropylpentanenitrile | n/a | C24H26N2O4 | 详情 | 详情 |
| (VI) | 53370 | 5-amino-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile | n/a | C16H24N2O2 | 详情 | 详情 |
| (VII) | 53371 | 2-Bromo-9-fluorenone | 3096-56-8 | C13H7BrO | 详情 | 详情 |
| (VIII) | 53372 | 5-({2-bromo-9-[(triisopropylsilyl)oxy]-9H-fluoren-9-yl}amino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile | n/a | C38H51BrN2O3Si | 详情 | 详情 |