8-(bromomethyl)-2-phenyl-4H-chromen-4-one -Drug Synthesis Database

【结构式】

【分子编号】22859

【品名】8-(bromomethyl)-2-phenyl-4H-chromen-4-one

【CA登记号】

【分子式】C₁₆H₁₁BrO₂

【分子量】315.16614

【元素组成】C 60.98% H 3.52% Br 25.35% O 10.15%

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：(I)

Treatment of 8-bromomethyl-2-phenylflavone (I) with KCN in EtOH-H2O for 3 h gives the nitrile intermediate (II) (m.p. 165-7 C) in 67% yield, which in diluted acetic-sulfuric acid is hydrolyzed to flavoneacetic acid (III) in 88% yield. On refluxing the potassium salt of the acid with 2-diethylaminoethyl chloride in acetone for 4 h, followed by converting the resulting ester to the hydrochloride salt, the diethylaminoethyl ester of flavoneacetic acid (m.p. 186 C) is produced in 70% yield.

参考文献中间体

合成目标

【1】 Briet, P.; Berthelon, J.J.; Collonges, F.; Atassi, G.; Synthesis and antitumor activity of some 8-substit. Eur J Med Chem 1985, 20, 393.
【2】 Berthelon, J.-J.; Collonges, F.; Briet, P. (Lipha Santé); 8-Haloalkyl-4H-(1)-benzopyran-4-ones and preparati. EP 0080419 .
【3】 Berthelon, J.-J.; Collonges, F.; Briet, P. (Lipha Santé); (Oxo-4-4H-(1)-benzopyran-8-yl) alkanoic acids, sal. EP 0080934; US 4602034 .
【4】 Berthelon, J.-J.; Collonges, F.; Briet, P. (Lipha Santé); 8-Haloalkyl-4H-1-benzopyran-4-ones and methods of . FR 2536396 .
【5】 Cheng, C.C.; Zee-Cheng, R.K.-Y.; Flavoneacetic acid. Drugs Fut 1987, 12, 2, 123.

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)	22859	8-(bromomethyl)-2-phenyl-4H-chromen-4-one		C₁₆H₁₁BrO₂	详情	详情
(II)	22860	2-(4-oxo-2-phenyl-4H-chromen-8-yl)acetonitrile		C₁₇H₁₁NO₂	详情	详情
(III)	22861	2-(4-oxo-2-phenyl-4H-chromen-8-yl)acetic acid		C₁₇H₁₂O₄	详情	详情
(IV)	16194	2-chloro-N,N-diethyl-1-ethanamine; N-(2-chloroethyl)-N,N-diethylamine	100-35-6	C₆H₁₄ClN	详情	详情

Extended Information