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【结 构 式】 
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【分子编号】40121 【品名】3-[(Z)-benzylidene]-2-benzofuran-1-one; Benzalphthalide; 3-[(Z)-benzylene]-1-isobenzofuranone; Benzylidenephthalide; 3-[(Z)-benzylene]-1(3H)-isobenzofuranone; 3-(Z)-Benzylidenephthalide 【CA登记号】575-61-1 |
【 分 子 式 】C15H10O2 【 分 子 量 】222.2432 【元素组成】C 81.07% H 4.54% O 14.4% |
合成路线1
该中间体在本合成路线中的序号：(XII)The starting product dibenzo[a,d]cyclohepta-1,4,6-triene-5-one (I) is prepared by condensation of phthalic anhydride (X) with phenylacetic acid (XI) by means of sodium acetate at 240 C that gives benzalphthalide (XII). This compound is reduced with red phosphorus in refluxing aqueous HI yielding 2-(2-phenylethyl)benzoic acid (XIII), which is then cyclized with polyphosphoric acid at 175 C afforing dibenzo[a,d]cyclohepta-1,4-diene-5-one (XIV). The ketone (XIV) is brominated with NBS in CCl4 to the bromo ketone (XV) and finally dehydrobrominated with triethylamine.
| 【1】 Roberts, P.J.; Castañer, J.; Cyclobenzaprine. Drugs Fut 1977, 2, 5, 299. |
| 【2】 Vilani, F.J. (Schering Corp.); 5-(3'-Dimethylamino-2'-methylpropyl)dibenzocycloheptenes. US 3409640 . |
| 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) | 29151 | 5H-dibenzo[a,d]cyclohepten-5-one; Dibenzosuberenone | 2222-33-5 | C15H10O | 详情 | 详情 |
| (X) | 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) | 16148 | Benzeneacetic acid; 2-Phenylacetic acid; Phenyl Acetic Acid | 103-82-2 | C8H8O2 | 详情 | 详情 |
| (XII) | 40121 | 3-[(Z)-benzylidene]-2-benzofuran-1-one; Benzalphthalide; 3-[(Z)-benzylene]-1-isobenzofuranone; Benzylidenephthalide; 3-[(Z)-benzylene]-1(3H)-isobenzofuranone; 3-(Z)-Benzylidenephthalide | 575-61-1 | C15H10O2 | 详情 | 详情 |
| (XIII) | 40122 | 2-phenethylbenzoic acid | 4890-85-1 | C15H14O2 | 详情 | 详情 |
| (XIV) | 40123 | 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one; Dibenzosuberone | 1210-35-1 | C15H12O | 详情 | 详情 |
| (XV) | 40124 | 10-bromo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one | C15H11BrO | 详情 | 详情 |