6-[(E)-nitromethylidene]-6,7,8,9-tetrahydronaphtho[1,2-d][1,3]dioxole -Drug Synthesis Database

【结构式】

【分子编号】33726

【品名】6-[(E)-nitromethylidene]-6,7,8,9-tetrahydronaphtho[1,2-d][1,3]dioxole

【CA登记号】

【分子式】C₁₂H₁₁NO₄

【分子量】233.22368

【元素组成】C 61.8% H 4.75% N 6.01% O 27.44%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XII)

The reaction of 6,7,8,9-tetrahydronaphtho[1,2-d][1,3]dioxol-6-one (I) with nitromethane by means of butylamine in refluxing toluene/methylcyclohexane/acetic acid gives the nitromethyl derivative (XIII), which is reduced with H2 over Pd/C in methanol to yield the previously described amine (VII). Amine (VII) can be condensed with 2-phenylsuccinic acid by means of acetyl chloride in refluxing xylene yielding directly the previously reported succinimide (X) as a mixture of the cis and trans racemic diastereomers.

参考文献中间体

合成目标

【1】 Deshpande, M.N.; et al.; A scalable process for the novel antidepressant ABT-200. Org Process Res Dev 1998, 2, 6, 351.

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)	33715	8,9-dihydronaphtho[1,2-d][1,3]dioxol-6(7H)-one		C₁₁H₁₀O₃	详情	详情
(VII)	33724	6,7,8,9-tetrahydronaphtho[1,2-d][1,3]dioxol-6-ylmethylamine; 6,7,8,9-tetrahydronaphtho[1,2-d][1,3]dioxol-6-ylmethanamine		C₁₂H₁₅NO₂	详情	详情
(X)	33722	3-phenyl-1-(6,7,8,9-tetrahydronaphtho[1,2-d][1,3]dioxol-6-ylmethyl)-2,5-pyrrolidinedione		C₂₂H₂₁NO₄	详情	详情
(XII)	33726	6-[(E)-nitromethylidene]-6,7,8,9-tetrahydronaphtho[1,2-d][1,3]dioxole		C₁₂H₁₁NO₄	详情	详情
(XIII)	33727	6-(nitromethyl)-8,9-dihydronaphtho[1,2-d][1,3]dioxole		C₁₂H₁₁NO₄	详情	详情
(XIV)	33728	2-phenylsuccinic acid	635-51-8	C₁₀H₁₀O₄	详情	详情

Extended Information