2,6-di(tert-butyl)-4-(chloromethyl)phenol -Drug Synthesis Database

【结构式】

【分子编号】62335

【品名】2,6-di(tert-butyl)-4-(chloromethyl)phenol

【CA登记号】

【分子式】C₁₅H₂₃ClO

【分子量】254.79972

【元素组成】C 70.71% H 9.1% Cl 13.91% O 6.28%

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：(II)

The title compound was prepared by several related methods. The sodium salt generated from tetraisopropyl methylenediphosphonate (I) and NaH was alkylated with 3,5-di-t-butyl-4-hydroxybenzyl chloride (II) in refluxing THF to afford the target arylethyl diphosphonate

参考文献中间体

合成目标

【1】 Nguyen, L.; Niesor, E.; Phan, H.; Maechler, P.; Bentzen, C. (Ilex Oncology Research-Europe SA); Phenol substd. gem-diphosphonate derivs., process for their preparation and pharmaceutical compsns. containing them. CH 675422; EP 0339237; JP 1990022285; US 5043330; US 5128331 .
【2】 Grinter, T.J.; Harris, M.A.; Hayler, J.D.; Negus, A. (Ilex Oncology Research-Europe SA); A process for the preparation of diphosphonate derivs.. WO 9731004 .

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)	27980	Diisopropyl (diisopropoxyphosphoryl)methylphosphonate; Tetraisopropyl methylenediphosphonate	1660-95-3	C₁₃H₃₀O₆P₂	详情	详情
(II)	62335	2,6-di(tert-butyl)-4-(chloromethyl)phenol		C₁₅H₂₃ClO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

In a related procedure, the dimethyl benzylamine (IV) was quaternized with iodomethane, and the resultant ammonium salt (V) was then condensed with the sodium salt of diphosphonate (I) (1). Other reported alkylating reagents included the bis-benzyl methyl amine (VII), prepared by Mannich reaction of methylamine with 2,6-di-t-butylphenol (VI) and formaldehyde, and the tris-benzyl amine (VIII), prepared by alkylation of ammonia with the benzyl chloride (II)

参考文献中间体

合成目标

【1】 Grinter, T.J.; Harris, M.A.; Hayler, J.D.; Negus, A. (Ilex Oncology Research-Europe SA); A process for the preparation of diphosphonate derivs.. WO 9731004 .

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)	27980	Diisopropyl (diisopropoxyphosphoryl)methylphosphonate; Tetraisopropyl methylenediphosphonate	1660-95-3	C₁₃H₃₀O₆P₂	详情	详情
(II)	62335	2,6-di(tert-butyl)-4-(chloromethyl)phenol		C₁₅H₂₃ClO	详情	详情
(IV)	62336	2,6-di(tert-butyl)-4-[(dimethylamino)methyl]phenol		C₁₇H₂₉NO	详情	详情
(V)	62338	[3,5-di(tert-butyl)-4-hydroxyphenyl]-N,N,N-trimethylmethanaminium iodide		C₁₈H₃₂INO	详情	详情
(VI)	25925	2,6-di(tert-butyl)phenol	128-39-2	C₁₄H₂₂O	详情	详情
(VII)	62339	2,6-di(tert-butyl)-4-{[[3,5-di(tert-butyl)-4-hydroxybenzyl](methyl)amino]methyl}phenol		C₃₁H₄₉NO₂	详情	详情
(VIII)	62340	4-({bis[3,5-di(tert-butyl)-4-hydroxybenzyl]amino}methyl)-2,6-di(tert-butyl)phenol		C₄₅H₆₉NO₃	详情	详情

合成路线3

该中间体在本合成路线中的序号：(II)

In a further method, condensation of benzyl alcohol (III) with methanol in the presence of a catalytic amount of HCl afforded the corresponding methyl ether (IX), which was then reacted with diphosphonate (I) in the presence of NaH to furnish the target arylethyl diphosphonate (1). Optionally, diphosphonate (I) was condensed with the benzyl acetate ester (X), prepared from benzyl chloride (II) and potassium acetate in acetone

参考文献中间体

合成目标

【1】 Grinter, T.J.; Harris, M.A.; Hayler, J.D.; Negus, A. (Ilex Oncology Research-Europe SA); A process for the preparation of diphosphonate derivs.. WO 9731004 .

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)	27980	Diisopropyl (diisopropoxyphosphoryl)methylphosphonate; Tetraisopropyl methylenediphosphonate	1660-95-3	C₁₃H₃₀O₆P₂	详情	详情
(II)	62335	2,6-di(tert-butyl)-4-(chloromethyl)phenol		C₁₅H₂₃ClO	详情	详情
(III)	37706	2,6-di(tert-butyl)-4-(hydroxymethyl)phenol	88-26-6	C₁₅H₂₄O₂	详情	详情
(IX)	62341	2,6-di(tert-butyl)-4-(methoxymethyl)phenol		C₁₆H₂₆O₂	详情	详情
(X)	62342	3,5-di(tert-butyl)-4-hydroxybenzyl acetate		C₁₇H₂₆O₃	详情	详情

Extended Information