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【结 构 式】 
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【分子编号】10246 【品名】N-Phenyl-2-[(triphenylstannyl)selanyl]benzamide 【CA登记号】 |
【 分 子 式 】C31H25NOSeSn 【 分 子 量 】625.21564 【元素组成】C 59.55% H 4.03% N 2.24% O 2.56% Se 12.63% Sn 18.99% |
合成路线1
该中间体在本合成路线中的序号：(III)A new synthesis of ebselen has been published: The radical reaction of 2-(benzylseleno)-N-phenylbenzamide (I) with triphenyltin hydride (II) and AIBN in refluxing benzene gives N-phenyl-2-(triphenylstannylseleno)benzamide (III), which is treated with dibenzoyl peroxide (IV) in refluxing benzene to yield the diselenide (V). Finally, the diselenide (V) was treated with di-tert-butyl peroxide (VI) in chlorobenzene at 120 C. This reaction cannot be carried out in refluxing benzene due to the extreme insolubility of (V) in benzene.
| 【1】 Fong, M.C.; Schiesser, C.H.; Reactions of 2,2'-diselenobis(N-alkylbenzamides) with peroxides: A free-radical synthesis of ebselen and related analogues. Tetrahedron Lett 1995, 36, 40, 7329. |
合成路线2
该中间体在本合成路线中的序号：(XXVIII)Alkylation of potassium phthalimide (XXVII) with epichlorohydrin (XXVIII) provided N-glycidyl phthalimide (XXIX). Epoxide ring opening in (XXIX) with aqueous HBr led to bromohydrin (XXX), which was further oxidized to bromo ketone (XXXI) by means of CrO3. Coupling of bromo ketone (XXXI) with diethyl malonate (XXXII) to afford (XXXIII) was accomplished in the presence of NaOEt in EtOH/DMF as the solvent. Acid hydrolysis of the malonate ester (XXXIII), followed by thermal decarboxylation, gave rise to phthalimido levulinic acid (XI). The phthaloyl group of (XI) was finally hydrolyzed under acidic conditions to furnish delta-aminolevulinic acid.
| 【1】 Collins, A.; Tschudy, D.P.; Malonic ester synthesis of delta-aminolevulinic acid. The reaction of N-3-bromoacetonylphthalimide with malonic ester. J Org Chem 1959, 24, 556. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XI) | 59147 | 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoic acid | C13H11NO5 | 详情 | 详情 | |
| (XXVII) | 27890 | Potassium phthalimide | 1074-82-4 | C8H4KNO2 | 详情 | 详情 |
| (XXVIII) | 10246 | N-Phenyl-2-[(triphenylstannyl)selanyl]benzamide | C31H25NOSeSn | 详情 | 详情 | |
| (XXIX) | 12335 | 2-(2-Oxiranylmethyl)-1H-isoindole-1,3(2H)-dione; N-(2,3-Epoxypropyl)phtalimide | 5455-98-1 | C11H9NO3 | 详情 | 详情 |
| (XXX) | 59158 | 2-(3-bromo-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione | C11H10BrNO3 | 详情 | 详情 | |
| (XXXI) | 59159 | 2-(3-Bromo-2-oxopropyl)isoindole-1,3-dione | C11H8BrNO3 | 详情 | 详情 | |
| (XXXII) | 16829 | Diethyl malonate | 105-53-3 | C7H12O4 | 详情 | 详情 |
| (XXXIII) | 59160 | diethyl 2-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-oxopropyl]malonate | C18H19NO7 | 详情 | 详情 |