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【结 构 式】 
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【分子编号】54839 【品名】7,12-bis(4-fluorophenyl)-2,17-diphenyl-21,23-dithia-22,24-diazapentacyclo[16.2.1.1~3,6~.1~8,11~.1~13,16~]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaene 【CA登记号】 |
【 分 子 式 】C44H26F2N2S2 【 分 子 量 】684.8327264 【元素组成】C 77.17% H 3.83% F 5.55% N 4.09% S 9.36% |
合成路线1
该中间体在本合成路线中的序号：(IX)Dilithiation of thiophene (I) employing an excess of BuLi in the presence of TMEDA produced the intermediate 2,5-dilithiothiophene (II). Addition of 4-fluorobenzaldehyde (III) to the organolithium compound (II) afforded the bis-carbinol adduct (IV). Alternatively, addition of benzaldehyde (V) to (II) provided adduct (VI). Boron trifluoride-catalyzed condensation of pyrrole (VII) with diol (IV) yielded the bis(alpha-pyrrolylbenzyl)thiophene (VIII). The dithiaporphyrin derivative (IX) was then obtained by condensation between (VIII) and (VI) in the presence of boron trifluoride. Finally, aromatic sulfonation of (IX) with hot sulfuric acid, followed by neutralization with NaOH furnished the title disulfonate disodium salt.
| 【1】 Hilmey, D.G.; et al.; Water-soluble, core-modified porphyrins as novel longer-wavelength-absorbing sensitizers for photodynamic therapy. II. Effects of core heteroatoms and meso-substituents on biological activity. J Med Chem 2002, 45, 2, 449. |
| 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) | 13297 | Thiophene | 110-02-1 | C4H4S | 详情 | 详情 |
| (II) | 54835 | C4H2Li2S | 详情 | 详情 | ||
| (III) | 12337 | 4-fluorobenzaldehyde | 459-57-4 | C7H5FO | 详情 | 详情 |
| (IV) | 54836 | (4-fluorophenyl){5-[(4-fluorophenyl)(hydroxy)methyl]-2-thienyl}methanol | C18H14F2O2S | 详情 | 详情 | |
| (V) | 10498 | Benzaldehyde;Benzoic aldehyde;Phenylmethanal | 100-52-7 | C7H6O | 详情 | 详情 |
| (VI) | 54837 | {5-[hydroxy(phenyl)methyl]-2-thienyl}(phenyl)methanol | C18H16O2S | 详情 | 详情 | |
| (VII) | 21674 | 1H-pyrrole | 109-97-7 | C4H5N | 详情 | 详情 |
| (VIII) | 54838 | 2-((4-fluorophenyl){5-[(4-fluorophenyl)(1H-pyrrol-2-yl)methyl]-2-thienyl}methyl)-1H-pyrrole | C26H20F2N2S | 详情 | 详情 | |
| (IX) | 54839 | 7,12-bis(4-fluorophenyl)-2,17-diphenyl-21,23-dithia-22,24-diazapentacyclo[16.2.1.1~3,6~.1~8,11~.1~13,16~]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaene | C44H26F2N2S2 | 详情 | 详情 |