2-phenethylbenzoic acid -Drug Synthesis Database

【结构式】

【分子编号】40122

【品名】2-phenethylbenzoic acid

【CA登记号】4890-85-1

【分子式】C₁₅H₁₄O₂

【分子量】226.27496

【元素组成】C 79.62% H 6.24% O 14.14%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XIII)

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.

参考文献中间体

合成目标

【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

Extended Information