4-Phenoxyphenol -Drug Synthesis Database

【结构式】

【分子编号】27080

【品名】4-Phenoxyphenol

【CA登记号】831-82-3

【分子式】C₁₂H₁₀O₂

【分子量】186.2102

【元素组成】C 77.4% H 5.41% O 17.18%

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：(VII)

The intermediate sulfone alcohol (V) has been obtained by an alternative procedure. 4-Phenoxyphenol (VII) was converted to thiophenol (IX) through the sequence of condensation with N,N-dimethylthiocarbamyl chloride, followed by thermal rearrangement of the resulting O-aryl thiocarbamate (VIII) to the S-aryl thiocarbamate, and then hydrolysis with KOH. Alkylation with 3-chloropropanol (II) provided thioether (X), which was then oxidized to the sulfone (V) with Oxone(R).

参考文献中间体

合成目标

【1】 Inturrisi, C.E.; Collins, J.J.; Dunkel, I.J.; Portenoy, R.K.; Palmer, L.N.; Lapin, J.; Gupta, S.K.; Weinstein, S.M.; Transdermal fentanyl in children with cancer pain: Feasibility, tolerability, and pharmacokinetic correlates. J Pediatr 1999, 134, 3, 319.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	19490	3-chloro-1-propanol	627-30-5	C₃H₇ClO	详情	详情
(V)	27078	3-[(4-phenoxyphenyl)sulfonyl]-1-propanol		C₁₅H₁₆O₄S	详情	详情
(VII)	27080	4-Phenoxyphenol	831-82-3	C₁₂H₁₀O₂	详情	详情
(VIII)	27081	O-(4-phenoxyphenyl) dimethylcarbamothioate		C₁₅H₁₅NO₂S	详情	详情
(IX)	26254	4-phenoxybenzenethiol; 4-phenoxyphenylhydrosulfide		C₁₂H₁₀OS	详情	详情
(X)	27082	3-[(4-phenoxyphenyl)sulfanyl]-1-propanol		C₁₅H₁₆O₂S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Treatment of 4-phenoxyphenol (I) with N,N-dimethylthiocarbamoyl chloride afforded the O-aryl thiocarbamate (II), which was thermally rearranged to the S-aryl thiocarbamate (III). Basic hydrolysis of (III) provided 4-phenoxythiophenol (IV). Subsequent alkylation of (IV) with allyl bromide (V) led to the allyl thioether (VI). Further oxidation of (VI) with m-chloroperbenzoic acid (MCPBA) gave rise to the epoxisulfone (VII). This was finally converted to the target thiirane derivative upon treatment with ammonium thiocyanate.

参考文献中间体

合成目标

【1】 Kotra, L.P.; Brown, S.; Bernardo, M.M.; Tanaka, Y.; Li, Z.-H.; Fridman, R.; Mobashery, S.; Potent and selective mechanism-based inhibition of gelatinases. J Am Chem Soc 2000, 122, 28, 6799.
【2】 Mobashery, S.; Fridman, R. (Wayne State University); Inhibitors of matrix metalloproteinases. WO 0192244 .

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)	27080	4-Phenoxyphenol	831-82-3	C₁₂H₁₀O₂	详情	详情
(II)	27081	O-(4-phenoxyphenyl) dimethylcarbamothioate		C₁₅H₁₅NO₂S	详情	详情
(III)	46031	S-(4-phenoxyphenyl) dimethylcarbamothioate		C₁₅H₁₅NO₂S	详情	详情
(IV)	26254	4-phenoxybenzenethiol; 4-phenoxyphenylhydrosulfide		C₁₂H₁₀OS	详情	详情
(V)	11463	3-Bromo-1-propene; 3-Bromopropene；allyl bromide	106-95-6	C₃H₅Br	详情	详情
(VI)	46032	1-(allylsulfanyl)-4-phenoxybenzene; 4-(allylsulfanyl)phenyl phenyl ether		C₁₅H₁₄OS	详情	详情
(VII)	46033	2-[[(4-phenoxyphenyl)sulfonyl]methyl]oxirane; 2-oxiranylmethyl 4-phenoxyphenyl sulfone		C₁₅H₁₄O₄S	详情	详情

Extended Information