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【结 构 式】 
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【分子编号】46633 【品名】dimethyl 2-[(E)-(4-iodo-1,3-benzodioxol-5-yl)methylidene]succinate 【CA登记号】 |
【 分 子 式 】C14H13IO6 【 分 子 量 】404.15809 【元素组成】C 41.61% H 3.24% I 31.4% O 23.75% |
合成路线1
该中间体在本合成路线中的序号：(III)The condensation of 4-iodo-1,3-benzodioxole-5-carbaldehyde (I) with dimethyl succinate (II) by means of NaOMe in aqueous methanol gives the benzylidene derivative (III), which is condensed with 1,3-benzodioxole-5-carbaldehyde (IV) by means of NaOMe in methanol, affording the bis-benzylidene hemiester (V). The selective reduction of (V) with LiEt3BH, followed by lactonization with ethyl chloroformate and TEA in THF, yields the lactone (VI), which is finally cyclized by means of Pd(OAc)2 and K2CO3 at 110 C through the nonisolated intermediate (VII), providing the target compound.
| 【1】 Mizufune, H.; et al.; The first regiospecific synthesis of helioxanthin by novel palladium-catalyzed benzannulation reaction of alpha,beta-bisbenzylidene-gamma-lactone. Tetrahedron Lett 2001, 42, 3, 437. |
| 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) | 46632 | 4-iodo-1,3-benzodioxole-5-carbaldehyde | C8H5IO3 | 详情 | 详情 | |
| (II) | 41056 | dimethyl succinate | 106-65-0 | C6H10O4 | 详情 | 详情 |
| (III) | 46633 | dimethyl 2-[(E)-(4-iodo-1,3-benzodioxol-5-yl)methylidene]succinate | C14H13IO6 | 详情 | 详情 | |
| (IV) | 10127 | 1,3-Benzodioxole-5-carbaldehyde; Heliotropine | 120-57-0 | C8H6O3 | 详情 | 详情 |
| (V) | 46634 | (E)-4-(1,3-benzodioxol-5-yl)-2-[(E)-(4-iodo-1,3-benzodioxol-5-yl)methylidene]-3-(methoxycarbonyl)-3-butenoic acid | C21H15IO8 | 详情 | 详情 | |
| (VI) | 46635 | 4-[(E)-1,3-benzodioxol-5-ylmethylidene]-3-[(E)-(4-iodo-1,3-benzodioxol-5-yl)methylidene]dihydro-2(3H)-furanone | C20H13IO6 | 详情 | 详情 | |
| (VII) | 46636 | [(10S)-10-(1,3-benzodioxol-5-yl)-7-oxo-7,10-dihydrofuro[3',4':6,7]naphtho[1,2-d][1,3]dioxol-9(9H)-yl](iodo)palladium | C20H13IO6Pd | 详情 | 详情 |