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【结 构 式】 
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【分子编号】59927 【品名】S-{4-[(3S,4R)-7-methoxy-3-phenyl-3,4-dihydro-2H-chromen-4-yl]phenyl} dimethylcarbamothioate 【CA登记号】 |
【 分 子 式 】C25H25NO3S 【 分 子 量 】419.54444 【元素组成】C 71.57% H 6.01% N 3.34% O 11.44% S 7.64% |
合成路线1
该中间体在本合成路线中的序号：(III)The previously described 4-hydroxyphenyl chromane derivative (I) was converted to the 4-sulfanylphenyl analogue (IV) via the following sequence. Condensation of the sodium salt of phenol (I) with N,N-dimethylthiocarbamoyl chloride gave the O-aryl thiocarbamate (II), which underwent further thermal rearrangement to the S-aryl thiocarbamate (III) in diphenyl ether at 260 C. Reductive cleavage of thiocarbamate (III) using LiAlH4 gave rise to thiophenol (IV). Subsequent alkylation of (IV) with N-(2-chloroethyl)pyrrolidine (V) yielded thioether (VI). The methyl ether function of (VI) was then cleaved by heating with pyridine hydrochloride, and the resultant compound was finally isolated as the corresponding hydrochloride salt.
| 【1】 Christiansen, L.B.; Weckens, M.; Bury, P.S.; Gissel, B.; Hansen, B.S.; Thorpe, S.M.; Jacobsen,P.; Kanstrup, A.; Jorgensen, A.S.; Naerum, L.; Wasserman, K.; Synthesis and biological evaluation of novel thio-substituted chromanes as high-affinity partial agonists for the estrogen receptor. Bioorg Med Chem Lett 2002, 12, 1, 17. |
| 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) | 35214 | 4-[(3S,4R)-7-methoxy-3-phenyl-3,4-dihydro-2H-chromen-4-yl]phenol | C22H20O3 | 详情 | 详情 | |
| (II) | 59926 | O-{4-[(3S,4R)-7-methoxy-3-phenyl-3,4-dihydro-2H-chromen-4-yl]phenyl} dimethylcarbamothioate | C25H25NO3S | 详情 | 详情 | |
| (III) | 59927 | S-{4-[(3S,4R)-7-methoxy-3-phenyl-3,4-dihydro-2H-chromen-4-yl]phenyl} dimethylcarbamothioate | C25H25NO3S | 详情 | 详情 | |
| (IV) | 59928 | 4-[(3S,4R)-7-methoxy-3-phenyl-3,4-dihydro-2H-chromen-4-yl]benzenethiol; 4-[(3S,4R)-7-methoxy-3-phenyl-3,4-dihydro-2H-chromen-4-yl]phenylhydrosulfide | C22H20O2S | 详情 | 详情 | |
| (V) | 33922 | 1-(2-Chloroethyl)pyrrolidine; N-(2-Chloroethyl)pyrrolidine | C6H12ClN | 详情 | 详情 | |
| (VI) | 59929 | 1-[2-({4-[(3S,4R)-7-methoxy-3-phenyl-3,4-dihydro-2H-chromen-4-yl]phenyl}sulfanyl)ethyl]pyrrolidine; methyl (3S,4R)-3-phenyl-4-(4-{[2-(1-pyrrolidinyl)ethyl]sulfanyl}phenyl)-3,4-dihydro-2H-chromen-7-yl ether | C28H31NO2S | 详情 | 详情 |