3-HYDROXY-3-METHYL-1,1-DIMETHOXYBUTANE, A NEW REAGENT FOR DIMETHYL-CHROMENYLATION - SYNTHESIS OF LONCHOCARPIN, JACAREUBIN, EVODIONOL METHYL ETHER, AND OTHER CHROMENS
3-HYDROXY-3-METHYL-1,1-DIMETHOXYBUTANE, A NEW REAGENT FOR DIMETHYL-CHROMENYLATION - SYNTHESIS OF LONCHOCARPIN, JACAREUBIN, EVODIONOL METHYL ETHER, AND OTHER CHROMENS
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DOI：
10.1039/j39710000811
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发表时间：
1971-01-01
期刊：
影响因子：
--
通讯作者：
WHITING, DA
中科院分区：
文献类型：
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作者：
BANDARANAYAKE, WM;CROMBIE, L;WHITING, DA
与柠檬醛一样，3-甲基丁-2-烯醛在吡啶催化下与合适的间二元酚缩合，得到具有自然界中常见的 2,2-二甲基取代模式的色烯。柠檬醛缩醛和3-甲基-1,1-二甲氧基丁-2-烯可以取代游离醛，这一观察结果导致了3-羟基-3-甲基-1,1-二甲氧基丁烷作为稳定且易于获得的二甲基苯并苯甲酰化试剂的开发。各种二甲基色酚的合成，其中包括 lonchocarpin、jacareubin 和 evodionol 甲基醚，说明了其用途。 But-2-enal 和肉桂醛可用于苯甲酰化反应。
Like citral, 3-methylbut-2-enal condenses under pyridine catalysis with suitable meta-dihydric phenols to give chromens having the 2,2-dimethyl-substitution pattern common in Nature. Citral acetal and 3-methyl-1,1-dimethoxybut-2-ene can replace the free aldehydes, and this observation has led to the development of 3-hydroxy-3-methyl-1,1-dimethoxybutane as a stable and readily accessible dimethylchromenylation reagent. Synthesis of various dimethylchromens, among them lonchocarpin, jacareubin, and evodionol methyl ether, illustrate its use. But-2-enal and cinnamaldehyde may be used in chromenylation reactions.