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【结 构 式】 
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【分子编号】17771 【品名】N,N-Dimethyl-p-aminobenzaldehyde; Ehrlich's reagent; p-Dimethylaminobenzaldehyde; 4-(dimethylamino)benzaldehyde 【CA登记号】100-10-7 |
【 分 子 式 】C9H11NO 【 分 子 量 】149.19248 【元素组成】C 72.46% H 7.43% N 9.39% O 10.72% |
合成路线1
该中间体在本合成路线中的序号：(I)The compound is prepared by aldol condensation between 4-dimethylaminobenzaldehyde (I) and imidazolyl acetophenone (II) in the presence of NaOH in methanol.
| 【1】 Cohen, F.E.; McKerrow, J.H.; Kenyon, G.L.; Li, Z.; Chen, X.; Gong, B.; Li, R. (University of California, Oakland); Inhibitors of metazoan parasite proteases. WO 9630004 . |
合成路线2
该中间体在本合成路线中的序号：(VI)The regioselective hydroboration of safrole (I), followed by oxidative work-up, furnished the primary alcohol (II). Jones oxidation of alcohol (II) yielded carboxylic acid (III), which was subsequently esterified by means of MeOH and H2SO4. Treatment of methyl ester (IV) with hydrazine gave hydrazide (V). This was finally condensed with 4-(dimethylamino)benzaldehyde (VI) to provide the title acyl hydrazone.
| 【1】 Lima, P.C.; et al.; Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole. Eur J Med Chem 2000, 35, 2, 187. |
| 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) | 46334 | 5-allyl-1,3-benzodioxole | C10H10O2 | 详情 | 详情 | |
| (II) | 46335 | 3-(1,3-benzodioxol-5-yl)-1-propanol | C10H12O3 | 详情 | 详情 | |
| (III) | 46336 | 3-(1,3-benzodioxol-5-yl)propionic acid | C10H10O4 | 详情 | 详情 | |
| (IV) | 46337 | methyl 3-(1,3-benzodioxol-5-yl)propanoate | C11H12O4 | 详情 | 详情 | |
| (V) | 46338 | 3-(1,3-benzodioxol-5-yl)propanohydrazide | C10H12N2O3 | 详情 | 详情 | |
| (VI) | 17771 | N,N-Dimethyl-p-aminobenzaldehyde; Ehrlich's reagent; p-Dimethylaminobenzaldehyde; 4-(dimethylamino)benzaldehyde | 100-10-7 | C9H11NO | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(II)The cyclization of 4-bromo-2-sulfanylaniline (I) with 4-(dimethylamino)benzaldehyde (II) by heating at 180 C in DMSO gives 6-bromo-2-[4-(dimethylamino)phenyl]benzothiazole (III), which is treated with (Bu3Sn)2 (IV) and Pd(PPh3)4 and TEA in dioxane to yield the tributyltin derivative (V). Finally, this compound is treated with 125INa and H2O2 in ethanol/water to afford the target radiolabeled compound.
| 【1】 Zhuang, Z.-P.; et al.; Radioiodinated styrylbenzenes and thioflavins as probes for amyloid aggregates. J Med Chem 2001, 44, 12, 1905. |
| 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) | 25571 | 2-amino-5-bromobenzenethiol; 2-amino-5-bromophenylhydrosulfide | C6H6BrNS | 详情 | 详情 | |
| (II) | 17771 | N,N-Dimethyl-p-aminobenzaldehyde; Ehrlich's reagent; p-Dimethylaminobenzaldehyde; 4-(dimethylamino)benzaldehyde | 100-10-7 | C9H11NO | 详情 | 详情 |
| (III) | 52427 | N-[4-(6-bromo-1,3-benzothiazol-2-yl)phenyl]-N,N-dimethylamine; 4-(6-bromo-1,3-benzothiazol-2-yl)-N,N-dimethylaniline | C15H13BrN2S | 详情 | 详情 | |
| (IV) | 52428 | Bis(tributyltin); Hexabutyldistannane; Bis(tri-n-butyltin); Hexa-n-butylditin; Hexa-n-butyldistannane | 813-19-4 | C24H54Sn2 | 详情 | 详情 |
| (V) | 52429 | N,N-dimethyl-N-{4-[6-(tributylstannanyl)-1,3-benzothiazol-2-yl]phenyl}amine; N,N-dimethyl-4-[6-(tributylstannanyl)-1,3-benzothiazol-2-yl]aniline | C27H40N2SSn | 详情 | 详情 |