5-allyl-1,3-benzodioxole -Drug Synthesis Database

【结构式】

【分子编号】46334

【品名】5-allyl-1,3-benzodioxole

【CA登记号】

【分子式】C₁₀H₁₀O₂

【分子量】162.1882

【元素组成】C 74.06% H 6.21% O 19.73%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

The regioselective hydroboration of safrole (I), followed by oxidative work-up, furnished the primary alcohol (II). Jones oxidation of alcohol (II) yielded carboxylic acid (III), which was subsequently esterified by means of MeOH and H2SO4. Treatment of methyl ester (IV) with hydrazine gave hydrazide (V). This was finally condensed with 4-(dimethylamino)benzaldehyde (VI) to provide the title acyl hydrazone.

参考文献中间体

合成目标

【1】 Lima, P.C.; et al.; Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole. Eur J Med Chem 2000, 35, 2, 187.

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)	46334	5-allyl-1,3-benzodioxole		C₁₀H₁₀O₂	详情	详情
(II)	46335	3-(1,3-benzodioxol-5-yl)-1-propanol		C₁₀H₁₂O₃	详情	详情
(III)	46336	3-(1,3-benzodioxol-5-yl)propionic acid		C₁₀H₁₀O₄	详情	详情
(IV)	46337	methyl 3-(1,3-benzodioxol-5-yl)propanoate		C₁₁H₁₂O₄	详情	详情
(V)	46338	3-(1,3-benzodioxol-5-yl)propanohydrazide		C₁₀H₁₂N₂O₃	详情	详情
(VI)	17771	N,N-Dimethyl-p-aminobenzaldehyde; Ehrlich's reagent; p-Dimethylaminobenzaldehyde; 4-(dimethylamino)benzaldehyde	100-10-7	C₉H₁₁NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Isosafrole (II) was obtained by isomerization of safrole (I) under basic conditions. Ozonolysis of (II), followed by reductive decomposition of the intermediate ozonide with Zn, furnished piperonal (III). Oxidation of aldehyde (III) with methanolic iodine produced the methyl ester (IV), which was converted to the corresponding hydrazide (V) upon treatment with hydrazine in refluxing EtOH. Finally, condensation of (V) with thiophene-2-carboxaldehyde (VI) yielded the title hydrazone.

参考文献中间体

合成目标

【1】 Gonzalez-Serratos, H.; et al.; A novel thienylhydrazone, (2-thienylidene)3,4-methylenedioxybenzoylhydrazine, increases inotropism and decreases fatigue of skeletal muscle. J Pharmacol Exp Ther 2001, 299, 2, 588.
【2】 Sudo, R.T.; Alburquerque, E.X.; De Barreiro, E.J. (University of Maryland); Thienylhydrazon with digitalis-like properties (positive inotropic effects). WO 0078754 .

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)	46334	5-allyl-1,3-benzodioxole		C₁₀H₁₀O₂	详情	详情
(II)	53072	5-[(E)-1-propenyl]-1,3-benzodioxole	n/a	C₁₀H₁₀O₂	详情	详情
(III)	10127	1,3-Benzodioxole-5-carbaldehyde; Heliotropine	120-57-0	C₈H₆O₃	详情	详情
(IV)	53073	methyl 1,3-benzodioxole-5-carboxylate	n/a	C₉H₈O₄	详情	详情
(V)	53074	1,3-benzodioxole-5-carbohydrazide	n/a	C₈H₈N₂O₃	详情	详情
(VI)	30732	2-thiophenecarbaldehyde; Thiophene-2-carboxaldehyde	98-03-3	C₅H₄OS	详情	详情

Extended Information