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【结 构 式】 
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【分子编号】23533 【品名】2-amino-5-methylphenol 【CA登记号】2835-98-5 |
【 分 子 式 】C7H9NO 【 分 子 量 】123.1546 【元素组成】C 68.27% H 7.37% N 11.37% O 12.99% |
合成路线1
该中间体在本合成路线中的序号：(A)Condensation of benzoil isothiocyanate (I) with 6-amino-m-cresol in refluxing acetone gives N-benzoyl-N'-(2-hydroxy-4-methylphenyl)thiourea (II), which is hydrolyzed with sodium hydroxide to afford N-(2-hydroxy-4-methyl(phenyl)thiourea (III). Thiazolyl ring closure is obtained by addition of chloroacetaldehyde diethylacetal in refluxing ethanol catalyzed by p-toluenesulfonic acid. 2-(2-Hydroxy-4-methylphenyl)aminothiazole is then converted to its hydrochloride sait by bubbling gaseous hydrochloric acid.
| 【1】 Alazet, A.; Bonne, C.; Coquelet, C.; Sincholle, D. (Chauvin Laboratories SA); N-Substd. 2-amino-thiazoles, process for their pre. EP 0202157; ES 8900045; FR 2581063; JP 1987077375; US 4785008 . |
| 【2】 Coquelet, C.; Bonne, C.; CBS-113 A. Drugs Fut 1987, 12, 6, 525. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 63311 | 2-chloro-1-ethoxyethyl ethyl ether; 2-chloro-1,1-diethoxyethane | C6H13ClO2 | 详情 | 详情 | ||
| (A) | 23533 | 2-amino-5-methylphenol | 2835-98-5 | C7H9NO | 详情 | 详情 |
| (I) | 23530 | benzoyl isothiocyanate | 532-55-8 | C8H5NOS | 详情 | 详情 |
| (II) | 23531 | N-benzoyl-N'-(2-hydroxy-4-methylphenyl)thiourea | C15H14N2O2S | 详情 | 详情 | |
| (III) | 23532 | N-(2-hydroxy-4-methylphenyl)thiourea | C8H10N2OS | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The target phenoxazinone is obtained by reaction of 2-amino-5-methylphenol (I) with Hemoglobin-O2, through the intermediate quinonimine (II). The reaction was performed with bovine hemolysates and also with purified human hemoglobin.
| 【1】 Tomoda, A.; Hamashima, H.; Arisawa, M.; Kikuchi, T.; Tezuka, Y.; Koshimura, S.; Phenoxazinone synthesis by human hemoglobin. Biochim Biophys Acta 1992, 117, 3, 306. |
| 【2】 Ishida, R.; Yamanaka, S.; Kawai, H.; Ito, H.; Iwai, M.; Nishizawa, M.; Hamatake, M.; Tomoda, A.; Antitumor activity of 2-amino-4,4 alpha-dihydro-4 alpha, 7-dimethyl-3H-phenoxazine-3-one, a novel phenoxazine derivative produced by the reaction of 2-amino-5-methylphenol with bovine hemolysate. Anti-Cancer Drugs 1996, 7, 5, 591. |
| 【3】 Tomoda, A.; Arai, S.; Ishida, R.; Shimamoto, T.; Ohnyashiki, K.; An improved method for the rapid preparation of 2-amino-4,4a-dihydro-4a,7-dimethyl-3H-phenoxazine-3-on, a novel antitumor agent. Bioorg Med Chem Lett 2001, 11, 8, 1057. |
| 【4】 Shimamoto, T.; Tomoda, A.; Ishida, R.; Ohyashiki, K.; Antitumor effects of a novel phenoxazine derivative on human leukemia cell lines in vitro and in vivo. Clin Cancer Res 2001, 7, 3, 704. |