10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one; Dibenzosuberone -Drug Synthesis Database

【结构式】

【分子编号】40123

【品名】10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one; Dibenzosuberone

【CA登记号】1210-35-1

【分子式】C₁₅H₁₂O

【分子量】208.25968

【元素组成】C 86.51% H 5.81% O 7.68%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

Addition of cyclopropylmagnesium bromide (II) to dibenzocycloheptanone (I) afforded the carbinol adduct (III), which was further rearranged to the bromopropylidene derivative (IV) upon treatment with bromotrimethylsilane. Alkylation of ethyl (R)-nipecotate (V) with bromide (IV) gave the tertiary amine (VI). The ethyl ester group of (VI) was finally hydrolyzed under basic conditions to furnish the corresponding carboxylic acid.

参考文献中间体

合成目标

【1】 Andersen, K.E.; Olsen, U.B.; Petersen, H.; Grønvald, F.C.; Sonnewald, U.; Jørgensen, T.K.; Andersen, H.S. (Novo Nordisk A/S); Novel heterocyclic cpds.. US 5595989; US 5668129; US 5688788; US 5693649; US 5712292; US 5721254; US 5795888; US 6043239; WO 9518793 .
【2】 Olsen, U.B. (Novo Nordisk A/S); Novel method. JP 1999507947; WO 9722338 .

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)	40123	10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one; Dibenzosuberone	1210-35-1	C₁₅H₁₂O	详情	详情
(II)	12450	Bromo(cyclopropyl)magnesium;cyclopropylmagnesium bromide;cyclopropylmagnesiumbromide	23719-80-4	C₃H₅BrMg	详情	详情
(III)	52138	5-cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol		C₁₈H₁₈O	详情	详情
(IV)	52139	5-(3-bromopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene		C₁₈H₁₇Br	详情	详情
(V)	35224	ethyl (3S)-3-piperidinecarboxylate		C₈H₁₅NO₂	详情	详情
(VI)	52140	ethyl (3R)-1-[3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-3-piperidinecarboxylate		C₂₆H₃₁NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIV)

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