4,10-Dioxatricyclo[5.2.1.0(2,6)]decane-3,5-dione -Drug Synthesis Database

【结构式】

【分子编号】49888

【品名】4,10-Dioxatricyclo[5.2.1.0(2,6)]decane-3,5-dione

【CA登记号】

【分子式】C₈H₈O₄

【分子量】168.14912

【元素组成】C 57.14% H 4.8% O 38.06%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(IX)

Hexachloroplatinic acid (I) was reduced to potassium tetrachloroplatinate (II) using hydrazine. Treatment of (II) with KI produced the tetraiodoplatinate (III), which was converted to the diamino compound (IV) by reaction with isopropylamine. Conversion to the dinitrate (V) was then effected by iodide ion exchange with silver nitrate. Diels-Alder condensation of maleic anhydride (VI) with furan (VII) furnished adduct (VIII), which was further hydrogenated to (IX) using Pd/C. Then, basic hydrolysis of the cyclic anhydride in the presence of the platinum complex (V) afforded the title compound.

参考文献中间体

合成目标

【1】 Lin, G.; To, K.K.W.; Wang, X.; Han, X.; Au-Yeung, S.C.F.; Ho, Y.-P.; Potential new antitumor agents from an innovative combination of demethylcantharidin, a modified traditional Chinese medicine, with a platinum moiety. J Med Chem 2001, 44, 13, 2065.
【2】 Ho, Y.P.; Au-Yeung, S.C.F.; Jiang, T.; Han, X.; Wang, X.; Lin, G.; Lu, S. (Chinese University of Hong Kong); Synthesis of platinum complexes and uses thereof. WO 9849174 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	11182	2,5-Furandione; Maleic anhydride	108-31-6	C₄H₂O₃	详情	详情
(VII)	22372	Furan	110-00-9	C₄H₄O	详情	详情
(VIII)	49887	exo-7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride; exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride; 7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride	6118-51-0	C₈H₆O₄	详情	详情
(IX)	49888	4,10-Dioxatricyclo[5.2.1.0(2,6)]decane-3,5-dione		C₈H₈O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The Diels-Alder cycloaddition between maleic anhydride (I) and furan (II) produced adduct (III). Subsequent double-bond hydrogenation in the presence of Pd/C furnished the saturated anhydride (IV).

参考文献中间体

合成目标

【1】 Lin, G.; To, K.K.W.; Wang, X.; Han, X.; Au-Yeung, S.C.F.; Ho, Y.-P.; Potential new antitumor agents from an innovative combination of demethylcantharidin, a modified traditional Chinese medicine, with a platinum moiety. J Med Chem 2001, 44, 13, 2065.
【2】 Ho, Y.P.; Au-Yeung, S.C.F.; Jiang, T.; Han, X.; Wang, X.; Lin, G.; Lu, S. (Chinese University of Hong Kong); Synthesis of platinum complexes and uses thereof. WO 9849174 .

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)	11182	2,5-Furandione; Maleic anhydride	108-31-6	C₄H₂O₃	详情	详情
(II)	22372	Furan	110-00-9	C₄H₄O	详情	详情
(III)	49887	exo-7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride; exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride; 7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride	6118-51-0	C₈H₆O₄	详情	详情
(IV)	49888	4,10-Dioxatricyclo[5.2.1.0(2,6)]decane-3,5-dione		C₈H₈O₄	详情	详情

合成路线3

该中间体在本合成路线中的序号：(IV)

The platinum nitrate derivative (X) was prepared by two related procedures. Halogen-exchange of potassium tetrachloroplatinate (V) with KI produced the tetraiodoplatinate (VI), which was subsequently reacted with trans-1,2-diaminocyclohexane (VII) to give the diamino chelate (VIII). Alternatively, diamine (VII) was reacted with tetrachloroplatinate (V), yielding chelate (IX). Treatment of either iodo compound (VIII) or its analogous chloride (IX) with silver nitrate furnished the dinitrate compound (X). Finally, the diacid formed by basic hydrolysis of anhydride (IV) was in situ complexed with the platinum compound (X) to generate the title platinum complex.

参考文献中间体

合成目标

【1】 Lin, G.; To, K.K.W.; Wang, X.; Han, X.; Au-Yeung, S.C.F.; Ho, Y.-P.; Potential new antitumor agents from an innovative combination of demethylcantharidin, a modified traditional Chinese medicine, with a platinum moiety. J Med Chem 2001, 44, 13, 2065.
【2】 Ho, Y.P.; Au-Yeung, S.C.F.; Jiang, T.; Han, X.; Wang, X.; Lin, G.; Lu, S. (Chinese University of Hong Kong); Synthesis of platinum complexes and uses thereof. WO 9849174 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	49888	4,10-Dioxatricyclo[5.2.1.0(2,6)]decane-3,5-dione		C₈H₈O₄	详情	详情
(V)	51693	dipotassium tetrachloroplatinate(2-);potassium tetrachloroplatinate(II);potassium tetrachloroplatinate	10025-99-7	Cl₄K₂Pt	详情	详情
(VI)	51694	dipotassium tetraiodoplatinate(2-);potassium tetraiodoplatinate(II);Potassium tetraiodoplatinate	14708-56-6	I₄K₂Pt	详情	详情
(VII)	11130	(1R,2R)-1,2-cyclohexanediamine; (1R,2R)-2-aminocyclohexylamine; cis-1,2-Diaminocyclohexane	20439-47-8	C₆H₁₄N₂	详情	详情
(VIII)	50042			C₆H₁₄I₂N₂Pt	详情	详情
(IX)	23063	(R,R)-Cyclohexane-1,2-diamine dichloro platinum complex		C₆H₁₄Cl₂N₂Pt	详情	详情
(X)	19480	(R,R)-Cyclohexane-1,2-diamine dinitrato platinum complex	n/a	C₆H₁₄N₄O₆Pt	详情	详情

Extended Information