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【结 构 式】 
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【分子编号】62709 【品名】methyl (E)-2-cyano-3-[4-(3-methyl-2-thienyl)phenyl]-2-butenoate 【CA登记号】 |
【 分 子 式 】C17H15NO2S 【 分 子 量 】297.37764 【元素组成】C 68.66% H 5.08% N 4.71% O 10.76% S 10.78% |
合成路线1
该中间体在本合成路线中的序号：(XXXV)The glycidic ester (XV), obtained as in Scheme 2, was alternatively rearranged to the alpha-keto ester enol form (XXXV) under acidic conditions. Hydrolysis and decarbonylation of (XXXV) employing NaOMe furnished acid (XI)
| 【2】 Arai, H.; Tanaka, K.; Watanabe, I.; Kodama, T.; Hirano, H.; Abe, N.; Nakabayashi, M. (Toyama Chemical Co., Ltd.); Novel 2-[4-(3-methyl-2-thienyl)phenyl]propionic acid and pharmaceutically acceptable salt thereof and method for treating symptoms of inflammation and pain. US 4230719 . |
| 【1】 Kodama, T.; Nakabayashi, M.; Watanabe, I.; Hirano, Y.; Abe, N.; Tanaka, K.; Arai, H. (Toyama Chemical Co., Ltd.); 2-[4-(3-Methyl-2-thienyl)phenyl]propionic acid derivs. and its non-toxic salts. DE 2850485; JP 1981049376 . |
合成路线2
该中间体在本合成路线中的序号：(XXXIX)A different strategy was based on the Knoevenagel condensation of ketone (XIV) with methyl cyanoacetate (XXXVIII) to produce the alkylidene cyanoacetate (XXXIX). Double-bond epoxidation by means of H2O2 led to (XL), which was further rearranged to keto amide (XLI). Decarboxylation of (XLI) under Hofmann rearrangement conditions furnished the arylpropionic acid (IX)
| 【2】 Arai, H.; Tanaka, K.; Watanabe, I.; Kodama, T.; Hirano, H.; Abe, N.; Nakabayashi, M. (Toyama Chemical Co., Ltd.); Novel 2-[4-(3-methyl-2-thienyl)phenyl]propionic acid and pharmaceutically acceptable salt thereof and method for treating symptoms of inflammation and pain. US 4230719 . |
| 【1】 Kodama, T.; Nakabayashi, M.; Watanabe, I.; Hirano, Y.; Abe, N.; Tanaka, K.; Arai, H. (Toyama Chemical Co., Ltd.); 2-[4-(3-Methyl-2-thienyl)phenyl]propionic acid derivs. and its non-toxic salts. DE 2850485; JP 1981049376 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 62687 | 2-[4-(3-methyl-2-thienyl)phenyl]propanoic acid | C14H14O2S | 详情 | 详情 | |
| (XIV) | 62689 | 1-[4-(3-methyl-2-thienyl)phenyl]-1-ethanone | C13H12OS | 详情 | 详情 | |
| (XXXVIII) | 34458 | Cyanoacetic acid methyl ester; methyl 2-cyanoacetate | 105-34-0 | C4H5NO2 | 详情 | 详情 |
| (XXXIX) | 62709 | methyl (E)-2-cyano-3-[4-(3-methyl-2-thienyl)phenyl]-2-butenoate | C17H15NO2S | 详情 | 详情 | |
| (XL) | 62710 | methyl 2-(aminocarbonyl)-3-methyl-3-[4-(3-methyl-2-thienyl)phenyl]-2-oxiranecarboxylate | C17H17NO4S | 详情 | 详情 | |
| (XLI) | 62711 | 3-[4-(3-methyl-2-thienyl)phenyl]-2-oxobutanamide | C15H15NO2S | 详情 | 详情 |