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【结 构 式】 
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【分子编号】53377 【品名】4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde 【CA登记号】128376-65-8 |
【 分 子 式 】C12H15BO3 【 分 子 量 】218.0603 【元素组成】C 66.1% H 6.93% B 4.96% O 22.01% |
合成路线1
该中间体在本合成路线中的序号：(III)The mono-Boc-protected diamine (II) was obtained by reaction of 1,4-diaminobutane (I) with Boc2O. Reductive alkylation of (II) to the benzylic amine (V) was carried out in a two-step procedure consisting in condensation of amine (II) with the formyl boronic ester (III) in the presence of molecular sieves, followed by reduction of the resultant imine (IV) with NaBH4. The N-Boc protecting group of (V) was then removed by acidic treatment, yielding diamine (VI). The title boronic acid was finally obtained by boronate ester exchange in (VI) with phenylboronic acid in a two-phase system.
| 【1】 Martin, B.; et al.; N'-Benzylpolyamines as vectors of boron and fluorine for cancer therapy and imaging: Synthesis and biological evaluation. J Med Chem 2001, 44, 22, 3653. |
| 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) | 42070 | 1,4-butanediamine; 4-aminobutylamine | 110-60-1 | C4H12N2 | 详情 | 详情 |
| (II) | 53376 | N-(4-Aminobutyl)carbamic acid tert-butyl ester; N-(tert-Butoxycarbonyl)-1,4-diaminobutane | 68076-36-8 | C9H20N2O2 | 详情 | 详情 |
| (III) | 53377 | 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde | 128376-65-8 | C12H15BO3 | 详情 | 详情 |
| (IV) | 53378 | tert-butyl 4-({(E)-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]methylidene}amino)butylcarbamate | n/a | C21H33BN2O4 | 详情 | 详情 |
| (V) | 53379 | tert-butyl 4-{[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzyl]amino}butylcarbamate | n/a | C21H35BN2O4 | 详情 | 详情 |
| (VI) | 53380 | N-(4-aminobutyl)-N-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzyl]amine; N~1~-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzyl]-1,4-butanediamine | n/a | C16H27BN2O2 | 详情 | 详情 |