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【结 构 式】 
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【分子编号】59159 【品名】2-(3-Bromo-2-oxopropyl)isoindole-1,3-dione 【CA登记号】 |
【 分 子 式 】C11H8BrNO3 【 分 子 量 】282.09346 【元素组成】C 46.84% H 2.86% Br 28.33% N 4.97% O 17.01% |
合成路线1
该中间体在本合成路线中的序号：(XXXI)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 |