2-(methylsulfanyl)phenol -Drug Synthesis Database

【结构式】

【分子编号】28075

【品名】2-(methylsulfanyl)phenol

【CA登记号】1073-29-6

【分子式】C₇H₈OS

【分子量】140.20592

【元素组成】C 59.97% H 5.75% O 11.41% S 22.87%

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：(III)

Reduction of 3-chloropropiophenone (I) with NaBH4 produced 3-chloro-1-phenyl-1-propanol (II). Subsequent Mitsunobu coupling of (II) with 2-(methylthio)phenol (III) in the presence of DEAD and PPh3 afforded ether (IV). Finally, substitution of the halogen of (IV) for methylamine provided the corresponding secondary amine.

参考文献中间体

合成目标

【1】 Gehlert, D.R.; Robertson, D.W.; Wong, D.T. (Eli Lilly and Company); N-Alkyl-3-phenyl-3-(2-alkylthiophenoxy)propylamines. EP 0591581 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	11021	Methanamine; Methylamine	74-89-5	CH₅N	详情	详情
(I)	28073	3-chloro-1-phenyl-1-propanone	936-59-4	C₉H₉ClO	详情	详情
(II)	28074	3-chloro-1-phenyl-1-propanol		C₉H₁₁ClO	详情	详情
(III)	28075	2-(methylsulfanyl)phenol	1073-29-6	C₇H₈OS	详情	详情
(IV)	28076	1-(3-chloro-1-phenylpropoxy)-2-(methylsulfanyl)benzene		C₁₆H₁₇ClOS	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The condensation of o-(methylthio)phenol (I) with epichlorohydrin (II) by means of sodium hydroxide in water gives 3-[o-(methylthio)phenoxy]-1,2-epoxypropane (III), which is then treated with isopropylamine (IV) in hot water and finally with ethanolic HCl

参考文献中间体

合成目标

【1】 (N.V. Philips' Gloeilampenfabrieken); BE 679005; CA 832495; DE 1543790; FR 1552786; FR 6393; GB 1137764; JP 6902978; NL 6504268; US 3542874; US 3632780 .
【2】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Weetman, D.F.; Tiprenolol hydrochloride. Drugs Fut 1979, 4, 11, 830.

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)	28075	2-(methylsulfanyl)phenol	1073-29-6	C₇H₈OS	详情	详情
(II)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(III)	60944	2-(methylsulfanyl)phenyl 2-oxiranylmethyl ether; 2-{[2-(methylsulfanyl)phenoxy]methyl}oxirane		C₁₀H₁₂O₂S	详情	详情
(IV)	23933	2-Propanamine; Isopropylamine	75-31-0	C₃H₉N	详情	详情
(V)	60945	1-(isopropylamino)-3-[2-(methylsulfanyl)phenoxy]-2-propanol		C₁₃H₂₁NO₂S	详情	详情

Extended Information