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【结 构 式】 
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【分子编号】11046 【品名】methyl 2-[6,7-dihydro-1-benzothiophen-4(5H)-ylidene]acetate 【CA登记号】 |
【 分 子 式 】C11H12O2S 【 分 子 量 】208.28108 【元素组成】C 63.43% H 5.81% O 15.36% S 15.4% |
合成路线1
该中间体在本合成路线中的序号：(III)A new synthesis of [14C]-PD-117302 has been described: The Reformatsky condensation of 4,5,6,7-tetrahydrobenzo[b]thiophen-4-one (II) with methyl [1-14C]-bromoacetate (I) by means of Zn in reflux toluene gives a mixture of methyl [1-14C]-2-(4,5,6,7-tetrahydrobenzothiophen-4-ylidene)acete (III) and methyl [1-14C]-2-(6,7-dihdyrobenzothiophen-4-yl)acetate (IV) which, without separation, are treated with Pd/C and S in refluxing N-methylpyrrolidone to afford methyl [1-14C]-2-(benzothiophen-4-yl)acetate (V). The hydrolysis of (V) with methanolic KOH yields the corresponding acid (VI), which is treated with refluxing SOCl2 to give the acyl chloride (VII). Finally, this compound is condensed with trans-1-[2-(methylamino)cyclohexyl]pyrrolidine (VIII) in dichloromethane ethyl ether.
| 【1】 Huang, C.C.; Hicks, J.L.; Butler, D.E.; Hays, S.J.; Synthesis of carbon-14 labeled PD 117,302 and PD 126,212, potential new analgesic agents. J Label Compd Radiopharm 1990, 28, 1, 15. |
| 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) | 11044 | methyl 2-bromo-2-methylpropanoate; methyl 2-bromo-2-methylpropionate | 23426-63-3 | C5H9BrO2 | 详情 | 详情 |
| (I) | 63069 | methyl 2-bromo-2-methylpropanoate | C5H9BrO2 | 详情 | 详情 | |
| (II) | 11045 | 6,7-Dihydro-1-benzothiophen-4(5H)-one; 4-Keto-4,5,6,7-tetrahydrothianaphthene; Tetrahydrobenzo(b)thiophene-4-one | 13414-95-4 | C8H8OS | 详情 | 详情 |
| (III) | 11046 | methyl 2-[6,7-dihydro-1-benzothiophen-4(5H)-ylidene]acetate | C11H12O2S | 详情 | 详情 | |
| (III) | 63070 | methyl 2-[6,7-dihydro-1-benzothiophen-4(5H)-ylidene]acetate | C11H12O2S | 详情 | 详情 | |
| (IV) | 11047 | methyl 2-(6,7-dihydro-1-benzothiophen-4-yl)acetate | C11H12O2S | 详情 | 详情 | |
| (IV) | 63071 | methyl 2-(6,7-dihydro-1-benzothiophen-4-yl)acetate | C11H12O2S | 详情 | 详情 | |
| (V) | 11048 | methyl 2-(1-benzothiophen-4-yl)acetate | C11H10O2S | 详情 | 详情 | |
| (V) | 63072 | methyl 2-(1-benzothiophen-4-yl)acetate | C11H10O2S | 详情 | 详情 | |
| (VI) | 11049 | 2-(1-Benzothiophen-4-yl)acetic acid | C10H8O2S | 详情 | 详情 | |
| (VI) | 63073 | 2-(1-benzothiophen-4-yl)acetic acid | C10H8O2S | 详情 | 详情 | |
| (VII) | 11050 | 2-(1-Benzothiophen-4-yl)acetyl chloride | C10H7ClOS | 详情 | 详情 | |
| (VII) | 63074 | 2-(1-benzothiophen-4-yl)acetyl chloride | C10H7ClOS | 详情 | 详情 | |
| (VIII) | 11051 | (1S,2S)-N-Methyl-2-(1-pyrrolidinyl)cyclohexanamine; N-Methyl-N-[(1S,2S)-2-(1-pyrrolidinyl)cyclohexyl]amine | C11H22N2 | 详情 | 详情 |