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【结 构 式】 
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【分子编号】59192 【品名】N-(tetrahydro-2-furanylmethyl)benzamide 【CA登记号】 |
【 分 子 式 】C12H15NO2 【 分 子 量 】205.25664 【元素组成】C 70.22% H 7.37% N 6.82% O 15.59% |
合成路线1
该中间体在本合成路线中的序号：(LXX)Tetrahydrofurfurylamine (XLVII) was converted into the corresponding phthalimide (XLVIII) by reaction of phthalic anhydride (V) in boiling chloroform. Subsequent ruthenium-catalyzed oxidation of (XLVIII) produced keto acid (XI), along with a pentanolide by-product, which was removed by column chromatography. Finally, acid hydrolysis of (XI) led to the desired compound. A closely related strategy was based in the ruthenium oxidation of N-benzoyl tetrahydrofurfurylamine (LXX), prepared from amine (XLVII) and benzoyl chloride (XLIX), to afford 5-benzoylaminolevulinic acid (XXXV), which was then hydrolyzed in boiling 6 N HCl .
| 【1】 Kawakami, H.; et al.; A new synthesis of 5-aminolevulinic acid. Agric Biol Chem 1991, 55, 6, 1687. |
| 【2】 Matsumoto, K.; Kawakami, H.; Koseki, K.; Ebata, T.; Matsushita, H. (Japan Tobacco Inc.); Method of preparing an acid additional salt of delta-aminolevulinic acid. US 5284973 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 11900 | 2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride | 85-44-9 | C8H4O3 | 详情 | 详情 |
| (XI) | 59147 | 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoic acid | C13H11NO5 | 详情 | 详情 | |
| (XXXV) | 59156 | 5-(benzoylamino)-4-oxopentanoic acid | C12H13NO4 | 详情 | 详情 | |
| (LXVII) | 27335 | Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine | 4795-29-3 | C5H11NO | 详情 | 详情 |
| (LXVIII) | 59191 | 2-(tetrahydro-2-furanylmethyl)-1H-isoindole-1,3(2H)-dione | C13H13NO3 | 详情 | 详情 | |
| (LXIX) | 10463 | Benzoyl chloride | 98-88-4 | C7H5ClO | 详情 | 详情 |
| (LXX) | 59192 | N-(tetrahydro-2-furanylmethyl)benzamide | C12H15NO2 | 详情 | 详情 |