2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione -Drug Synthesis Database

【结构式】

【分子编号】60269

【品名】2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione

【CA登记号】

【分子式】C₁₅H₁₄O₃

【分子量】242.27436

【元素组成】C 74.36% H 5.82% O 19.81%

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：(VII)

Oxidative cleavage of methylindene (I) by means of Na2Cr2O7 produces 2-acetylphenylacetic acid (II). Fischer esterification of keto acid (II) gives keto ester (III), which is subjected to intramolecular Claisen condensation and air oxidation, yielding the hydroxy naphthoquinone (IV) (1). Alkylation of (IV) with prenyl bromide (V) leads to a mixture of lapachol (VII) and minor amounts of the prenyl ether isomer (VI) (1-3). Finally, cyclization of (VII) in concentrated H2SO4 gives rise to the target compound.

参考文献中间体

合成目标

【1】 Sun, J.S.; Geiser, A.H.; Frydman, B.; A preparative synthesis of lapachol and related naphthoquinones. Tetrahedron Lett 1998, 39, 8221.
【2】 Schaffner-Sabba, K.; Schmidt-Ruppin, K.H..; Wehrli, W.; Schuerch, A.R.; Wasley, J.W.F.; beta-Lapachone: Synthesis of derivatives and activities in tumor models. J Med Chem 1984, 27, 8, 990.
【3】 Boothman, D.A.; Frydman, B.J.; Witiak, D.T. (Wisconsin Alumni Research Foundation); Novel synthesis and use of beta-lapachone analogs. US 5763625; WO 9633988 .
【4】 Jiang, Z.; Hogeland, J. (Dana-Farber Cancer Institute); Synthesis of beta-lapachone and its intermediates. WO 0259103 .

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)	60264	3-methyl-1H-indene		C₁₀H₁₀	详情	详情
(II)	60265	2-(2-acetylphenyl)acetic acid		C₁₀H₁₀O₃	详情	详情
(III)	60266	ethyl 2-(2-acetylphenyl)acetate		C₁₂H₁₄O₃	详情	详情
(IV)	60267	2-hydroxy-1,4-naphthalenedione		C₁₀H₆O₃	详情	详情
(V)	51796	Prenyl Chloride; 1-Chloro-3-methyl-2-butene	503-60-6	C₅H₉Cl	详情	详情
(VI)	60268	2-[(3-methyl-2-butenyl)oxy]-1,4-naphthalenedione		C₁₅H₁₄O₃	详情	详情
(VII)	60269	2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione		C₁₅H₁₄O₃	详情	详情

Extended Information