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【结 构 式】 
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【分子编号】32595 【品名】methyl 6-[[(4-chlorophenyl)sulfonyl]amino]-2-(trimethylsilyl)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate 【CA登记号】 |
【 分 子 式 】C21H26ClNO4SSi 【 分 子 量 】452.04598 【元素组成】C 55.8% H 5.8% Cl 7.84% N 3.1% O 14.16% S 7.09% Si 6.21% |
合成路线1
该中间体在本合成路线中的序号：(III)Diels-Alder condensation of benzopyran (I) with methyl (trimethylsilyl)propynoate (II) gave rise to tetrahydronaphthalene (III). After reduction of the ester group of (III) with LiAlH4, the resulting alcohol (IV) was further oxidized to aldehyde (V) by means of 4-benzylpyridinium dichromate. Treatment of (V) with iodine monochloride produced iodonaphthalene (VI). Subsequent reaction of (VI) with vinyl tributyltin and palladium tetrakis(triphenylphosphine) yielded the vinyl naphthalene (VII). Wittig reaction of (VIII with (carbomethoxymethylidene)triphenylphosphorane (VIII) gave the arylpropenoate ester (IX), which was reduced to the saturated ester (X) employing samarium iodide.
| 【1】 Lavielle, G.; Cimetiere, B.; Verbeuren, T.; Simonet, S.; Descombes, J.-J. (ADIR et Cie.); Nouveaux dérivés de benzènsessulfonylamine, leur procédé depréparation et les compositions pharmaceutiques qui les contiennent. EP 0864561 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 24920 | tributyl(vinyl)stannane；Tributylvinylstannane;Vinyltributylstannane | 7486-35-3 | C14H30Sn | 详情 | 详情 | |
| (I) | 19586 | 4-chloro-N-(2-oxo-5,6,7,8-tetrahydro-2H-chromen-6-yl)benzenesulfonamide | C15H14ClNO4S | 详情 | 详情 | |
| (II) | 32594 | methyl 3-(trimethylsilyl)-2-propynoate | C7H12O2Si | 详情 | 详情 | |
| (III) | 32595 | methyl 6-[[(4-chlorophenyl)sulfonyl]amino]-2-(trimethylsilyl)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate | C21H26ClNO4SSi | 详情 | 详情 | |
| (IV) | 32596 | 4-chloro-N-[5-(hydroxymethyl)-6-(trimethylsilyl)-1,2,3,4-tetrahydro-2-naphthalenyl]benzenesulfonamide | C20H26ClNO3SSi | 详情 | 详情 | |
| (V) | 32597 | 4-chloro-N-[5-formyl-6-(trimethylsilyl)-1,2,3,4-tetrahydro-2-naphthalenyl]benzenesulfonamide | C20H24ClNO3SSi | 详情 | 详情 | |
| (VI) | 19571 | 4-chloro-N-(5-formyl-6-iodo-1,2,3,4-tetrahydro-2-naphthalenyl)benzenesulfonamide | C17H15ClINO3S | 详情 | 详情 | |
| (VII) | 32598 | 4-chloro-N-(5-formyl-6-vinyl-1,2,3,4-tetrahydro-2-naphthalenyl)benzenesulfonamide | C19H18ClNO3S | 详情 | 详情 | |
| (VIII) | 14689 | Methyl (triphenylphosphoranylidene)acetate; (methoxycarbonylmethylene)triphenylphosphorane；Methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate | 2605-67-6 | C21H19O2P | 详情 | 详情 |
| (IX) | 32599 | methyl (E)-3-(6-[[(4-chlorophenyl)sulfonyl]amino]-2-vinyl-5,6,7,8-tetrahydro-1-naphthalenyl)-2-propenoate | C22H22ClNO4S | 详情 | 详情 | |
| (X) | 32600 | methyl 3-(6-[[(4-chlorophenyl)sulfonyl]amino]-2-vinyl-5,6,7,8-tetrahydro-1-naphthalenyl)propanoate | C22H24ClNO4S | 详情 | 详情 |