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【结 构 式】 
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【分子编号】43130 【品名】2,2'-Bithiophene 【CA登记号】492-97-7 |
【 分 子 式 】C8H6S2 【 分 子 量 】166.26764 【元素组成】C 57.79% H 3.64% S 38.57% |
合成路线1
该中间体在本合成路线中的序号：(I)Formylation of 2,2'-bithiophene (I) either under Vilsmeier conditions (1) or by lithiation with LDA, followed by addition of DMF (2), provided aldehyde (II). This was protected as the dimethyl acetal (III) employing trimethyl orthoformate in the presence of montmorillonite K-10. After lithiation of (III) with n-BuLi, treatment with tributyltin chloride gave the stannyl derivative (IV). Stille coupling of (IV) with 2-iodo-4-(hydroxymethyl)thiophene (VI) (prepared by reduction of the corresponding aldehyde (V) with NaBH4), furnished the corresponding terthiophene, which after acid hydrolysis of the acetal protecting group provided the title compound.
| 【1】 Xu, W.-C.; Chang, C.-j.; Zhou, Q.; Ashendel, C.L.; Chang, C.t.; Novel protein kinase C inhibitors: Synthesis and PKC inhibition of beta-substituted polythiophene derivatives. Bioorg Med Chem Lett 1999, 9, 15, 2279. |
| 【2】 Chang, C.-T.; Chang, C.-J.; Lee, C.-T.; Lin, F.-L.; Tsai, J.-D.; Ashendel, C.L.; Chan, T.C.K.; Geahlen, R.L.; Waters, D.J. (Industrial Technology & Research Institute; Purdue Research Foundation); Polythiophene anti-tumor agents. EP 1007035; WO 9823269 . |
| 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) | 43130 | 2,2'-Bithiophene | 492-97-7 | C8H6S2 | 详情 | 详情 |
| (II) | 43131 | 2,2'-Bithienyl-5-carboxaldehyde 2,2'-Bithienyl-5-carboxaldehyde 2,2'-Bithienyl-5-carboxaldehyde | 3779-27-9 | C9H6OS2 | 详情 | 详情 |
| (III) | 43132 | C11H12O2S2 | 详情 | 详情 | ||
| (IV) | 43133 | C23H38O2S2Sn | 详情 | 详情 | ||
| (V) | 43134 | 5-iodo-3-thiophenecarbaldehyde | 18799-85-4 | C5H3IOS | 详情 | 详情 |
| (VI) | 43135 | (5-iodo-3-thienyl)methanol | C5H5IOS | 详情 | 详情 |