3-chloro-2-(chloromethyl)-1-propene -Drug Synthesis Database

【结构式】

【分子编号】64026

【品名】3-chloro-2-(chloromethyl)-1-propene

【CA登记号】

【分子式】C₄H₆Cl₂

【分子量】124.99704

【元素组成】C 38.44% H 4.84% Cl 56.73%

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：(IV)

Reduction of artemisinin (I) with DIBAL, followed by acetylation of the resultant lactol (II) with Ac2O/DMAP leads to dihydroartemisinin acetate (III). Treatment of the allylic dichloride (IV) with trimethylsilyllithium provides the bis-silane derivative (V). Then, coupling of dihydroartemisinin acetate (III) with bis-silane (V) in the presence of SnCl4 gives rise to the artemisinin dimer (VI).

参考文献中间体

合成目标

【1】 Posner, G.H.; Paik, I.-P.; Sur, S.; McRiner, A.J.; Borstnik, K.; Zie, S.; Shapiro, T.A.; Orally active, antimalarial, anticancer, artemisinin-derived trioxane dimers with high stability and efficacy. J Med Chem 2003, 46, 6, 1060.

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)	22369	Qinghaosu; Artemisine; (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-one	63968-64-9	C₁₅H₂₂O₅	详情	详情
(II)	22370	Dihydroartemisinin; (1R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-ol		C₁₅H₂₄O₅	详情	详情
(III)	56087	(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl acetate		C₁₇H₂₆O₆	详情	详情
(IV)	64026	3-chloro-2-(chloromethyl)-1-propene		C₄H₆Cl₂	详情	详情
(V)	64027	trimethyl{2-[(trimethylsilyl)methyl]-2-propenyl}silane		C₁₀H₂₄Si₂	详情	详情
(VI)	64028	(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-10-(2-{[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]methyl}-2-propenyl)-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadecane		C₃₄H₅₂O₈	详情	详情

Extended Information