7-hydroxy-7-phenylheptanoic acid -Drug Synthesis Database

【结构式】

【分子编号】31149

【品名】7-hydroxy-7-phenylheptanoic acid

【CA登记号】

【分子式】C₁₃H₁₈O₃

【分子量】222.28412

【元素组成】C 70.24% H 8.16% O 21.59%

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：(V)

The reaction of pimelic acid monoester (I) with refluxing SOCl2 gives the corresponding acid chloride (II), which by a Friedel-Craft's condensation with benzene (AlCl3 as catalyst) is converted into 6-benzoylhexanoic acid ethyl ester (III). The reduction of (III) with NaBH4 in methanol affords 7-hydroxy-7-phenylheptanoic acid ethyl ester (IV), which is hydrolyzed with NaOH in hot THF - water to yield the corresponding free acid (V). Finally, this compound is condensed with trimethylhydroquinone (VI) by means of boron trifluoride ethearate in hot toluene.

参考文献中间体

合成目标

【1】 Terao, S.; Maki, Y. (Takeda Chemical Industries, Ltd.); Quinone amides, their production and use. EP 0232089; JP 1987246545 .
【2】 Terao, S.; Maki, Y. (Takeda Chemical Industries, Ltd.); Quinone derivs., their production and use. AU 8545615; EP 0171251; ES 8704870; JP 1986044840; JP 1991072444; JP 1991081248; JP 1991086841; US 5180742; WO 8600887; WO 8604058 .
【3】 Shiraishi, M.; Kato, K.; Terao, S.; Ashida, Y.; Terashita, Z.-I.; Kito, G.; Quinones. 4. Novel eicosanoid antagonists: Synthesis and pharmacological evaluation. J Med Chem 1989, 32, 9, 2214-21.
【4】 Terao, S.; Quinone derivatives: Synthesis and structure-activity relations of a novel class of eicosanoid antagonists, AA-2414 and its analogs. Advances in Prostaglandin, Thromboxane and Leukotriene Research 1989, 19, 651-654.
【5】 Prous, J.; Castaner, J.; AA-2414. Drugs Fut 1990, 15, 8, 783.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	13364	Benzene	71-43-2	C₆H₆	详情	详情
(I)	31145	7-ethoxy-7-oxoheptanoic acid	33018-91-6	C₉H₁₆O₄	详情	详情
(II)	31146	ethyl 7-chloro-7-oxoheptanoate	14794-32-2	C₉H₁₅ClO₃	详情	详情
(III)	31147	ethyl 7-oxo-7-phenylheptanoate		C₁₅H₂₀O₃	详情	详情
(IV)	31148	ethyl 7-hydroxy-7-phenylheptanoate		C₁₅H₂₂O₃	详情	详情
(V)	31149	7-hydroxy-7-phenylheptanoic acid		C₁₃H₁₈O₃	详情	详情
(VI)	26357	2,3,5-trimethyl-1,4-benzenediol	700-13-0	C₉H₁₂O₂	详情	详情

Extended Information