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【结 构 式】 
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【分子编号】27081 【品名】O-(4-phenoxyphenyl) dimethylcarbamothioate 【CA登记号】 |
【 分 子 式 】C15H15NO2S 【 分 子 量 】273.35564 【元素组成】C 65.91% H 5.53% N 5.12% O 11.71% S 11.73% |
合成路线1
该中间体在本合成路线中的序号：(VIII)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).
| 【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：(II)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.
| 【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 |