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【结 构 式】

【分子编号】31622

【品名】1-(3,5-difluorophenyl)-2-[4-(methylsulfanyl)phenyl]-2-propen-1-ol

【CA登记号】

【 分 子 式 】C16H14F2OS

【 分 子 量 】292.3493664

【元素组成】C 65.74% H 4.83% F 13% O 5.47% S 10.97%

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 4-(methylsulfanyl)acetophenone (I) with tosylhydrazine by means of PPTS in acetonitrile gives the corresponding hydrazone (II), which by reaction with isopropylmagnesium chloride in THF/toluene yields the vinylmagnesium derivative (III). This compound, without isolation is condensed with 3,5-difluorobenzaldehyde (IV) to afford the allyl alcohol (V), which is condensed with triethyl orthoacetate and saponified providing 5-(3,5-difluorophenyl)-4-[4-(methylsulfanyl)phenyl]-4-pentenoic acid (VI). The cyclization of (VI) with AlCl3 and (COCl)2 in dichloromethane gives the cyclopentenone (VII), which is finally oxidized with potassium peroxymonosulfate (Oxone) in hot acetone/water to afford the target sulfone.

1 Grabowski, E.J.J.; Zhaol, D.L.; Prasit, P.; Xu, F.; Ouimet, N.; Tillyer, R.D.; Black, C.; Chen, C.Y.; Reider, P.J.; Efficient syntheses of 2-(3 ',5 '-difluorophenyl)-3-(4 '-methylsulfonylphenyl)-cyclopent-2-enone, a potent COX-2 inhibitor. Tetrahedron 1999, 55, 19, 6001.
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) 19262 1-[4-(methylsulfanyl)phenyl]-1-ethanone;4'-Methylthioacetophenon;4’-(methylthio)acetophenone 1778-09-2 C9H10OS 详情 详情
(II) 31619 4-methyl-N'-[(E)-1-[4-(methylsulfanyl)phenyl]ethylidene]benzenesulfonohydrazide C16H18N2O2S2 详情 详情
(III) 31620 chloro[1-[4-(methylsulfanyl)phenyl]vinyl]magnesium C9H9ClMgS 详情 详情
(IV) 31621 3,5-difluorobenzaldehyde 32085-88-4 C7H4F2O 详情 详情
(V) 31622 1-(3,5-difluorophenyl)-2-[4-(methylsulfanyl)phenyl]-2-propen-1-ol C16H14F2OS 详情 详情
(VI) 31623 (Z)-5-(3,5-difluorophenyl)-4-[4-(methylsulfanyl)phenyl]-4-pentenoic acid C18H16F2O2S 详情 详情
(VII) 25955 2-(3,5-difluorophenyl)-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one C18H14F2OS 详情 详情
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