3-amino-2-cyclohexen-1-one -Drug Synthesis Database

【结构式】

【分子编号】31475

【品名】3-amino-2-cyclohexen-1-one

【CA登记号】5220-49-5

【分子式】C₆H₉NO

【分子量】111.1436

【元素组成】C 64.84% H 8.16% N 12.6% O 14.4%

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：(II)

The reaction of cyclohexane-1,3-dione (I) with ammonia gives 3-amino-2-cyclohexen-1-one (II), which is cyclized with acrylic acid (III) by heating at 140 C yielding 1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione (IV). The dehydrogenation of (IV) by means of Pd/C in refluxing decaline affords 5-hydroxy-1,2,3,4-tetrahydroquinolin-2-one (V), which is condensed with epichlorohydrin (VI) by means of NaOMe or NaOH in methanol giving 5-(2,3-epoxypropoxy)-1,2,3,4-tetrahydroquinolin-2-one (VII). Finally, this compound is treated with tert-butylamine in methanol.

参考文献中间体

合成目标

【1】 Castaner, J.; Sungurbey, K.; Carteolol. Drugs Fut 1977, 2, 5, 288.
【2】 Shono, T.; et al.; A new practical synthesis of 5-hydroxy-3,4-dihydrocarbostyril and 5-hydroxycarbostyril. J Org Chem 1981, 46, 3719.
【3】 Von Winkler, W.; Chemical and analytical data for the pharmaceutically active substance carteolol hydrochloride. Arzneim-Forsch Drug Res 1983, 33, 2a, 279.
【4】 Mori, H.; Tamura, Y,.; Tominaga, M.; Yoshiaki, S.; Nakagawa, K.; Murakami, N. (Otsuka Pharmaceutical Co., Ltd.); 3,4-Dihydrocarbostyril derivs., their preparation, and pharmaceutical compsns. thereof. DE 2302027; GB 1424571 .

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)	11244	1,3-Cyclohexanedione	504-02-9	C₆H₈O₂	详情	详情
(II)	31475	3-amino-2-cyclohexen-1-one	5220-49-5	C₆H₉NO	详情	详情
(III)	19139	acrylic acid	79-10-7	C₃H₄O₂	详情	详情
(IV)	31476	4,6,7,8-tetrahydro-2,5(1H,3H)-quinolinedione		C₉H₁₁NO₂	详情	详情
(V)	31477	5-hydroxy-3,4-dihydro-2(1H)-quinolinone		C₉H₉NO₂	详情	详情
(VI)	29648	2-oxiranylmethanol	556-52-5	C₃H₆O₂	详情	详情
(VII)	31478	5-(2-oxiranylmethoxy)-3,4-dihydro-2(1H)-quinolinone		C₁₂H₁₃NO₃	详情	详情
(VIII)	17895	2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine	75-64-9	C₄H₁₁N	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The Hantzsch reaction between 3-oxotetrahydrothiophene-1,1-dioxide (I), 3-bromo-4-fluorobenzaldehyde (II) and 3-amino-2-cyclohexen-1-one (III) in refluxing EtOH yielded the hydroxy tetrahydropyridine derivative (IV). Dehydration of the cyclic hemiaminal function of (IV) was carried out in refluxing toluene to produce the racemic dihydropyridine, which was resolved into the individual enantiomers by chiral HPLC.

参考文献中间体

合成目标

【1】 Drizin, I.; et al.; Novel sulfonyldihydropyridine potassium channel openers with potential utility in the treatment of overactive bladder (OAB). 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 197.
【2】 Drizin, I.; Holladay, M.W.; Carroll, W.A.; Zhang, H.Q.; Sullivan, J.P. (Abbott Laboratories Inc.); Potassium channel openers. EP 1040097; US 6265417; WO 9931059 .

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)	51549	3-Oxosulfolane		C₄H₆O₃S	详情	详情
(II)	51550	3-Bromo-4-fluorobenzaldehyde	77771-02-9	C₇H₄BrFO	详情	详情
(III)	31475	3-amino-2-cyclohexen-1-one	5220-49-5	C₆H₉NO	详情	详情
(IV)	51551	9-(3-bromo-4-fluorophenyl)-3a-hydroxy-2,3,3a,5,6,7,9,9a-octahydro-1H-2H-thieno[3,2-b]quinoline-1,1,8(4H)-trione		C₁₇H₁₇BrFNO₄S	详情	详情

Extended Information