1-(3-methoxyphenyl)acetone -Drug Synthesis Database

【结构式】

【分子编号】29663

【品名】1-(3-methoxyphenyl)acetone

【CA登记号】3027-13-2

【分子式】C₁₀H₁₂O₂

【分子量】164.20408

【元素组成】C 73.15% H 7.37% O 19.49%

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：(II)

The reaction of ethanolimine (I) with m-methoxyphenylacetone (II) gives the corresponding Schiff base (III), which is reduced with H2 over Pd/C to the corresponding secondary amine (IV). Methylation of (IV) with HCHO-HCOOH yields 1-(m-methoxyphenyl)-2-(N-(2-hydroxyethyl)-N-methylaminoipropane (V), which is treated with SOCl2 to afford the 2-chloroethyl derivative (VI). Finally, this compound is condensed with benzhydrol (VII) by means of NaNH2 in refluxing benzene, and treated with HCl.

参考文献中间体

合成目标

【1】 Lindner, E.; Ehrhart, G.; Ott, H. (Aventis Pharma AG); m-Methoxy-alpha-methyl-phenethyl-amino-diphenylmethyl ethers. US 3565955 .
【2】 Mannhold, R.; HOE-263. Drugs Fut 1985, 10, 6, 458.

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)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情
(II)	29663	1-(3-methoxyphenyl)acetone	3027-13-2	C₁₀H₁₂O₂	详情	详情
(III)	29664	2-[[(E)-2-(3-methoxyphenyl)-1-methylethylidene]amino]-1-ethanol		C₁₂H₁₇NO₂	详情	详情
(IV)	29665	2-[[2-(3-methoxyphenyl)-1-methylethyl]amino]-1-ethanol		C₁₂H₁₉NO₂	详情	详情
(V)	29666	2-[[2-(3-methoxyphenyl)-1-methylethyl](methyl)amino]-1-ethanol		C₁₃H₂₁NO₂	详情	详情
(VI)	29667	N-(2-chloroethyl)-N-[2-(3-methoxyphenyl)-1-methylethyl]-N-methylamine; N-(2-chloroethyl)-1-(3-methoxyphenyl)-N-methyl-2-propanamine		C₁₃H₂₀ClNO	详情	详情
(VII)	11845	Diphenylmethanol; Benzhydrol	91-01-0	C₁₃H₁₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(A)

3beta-Hydroxy-5-androsten-17-one (XVII) is dihydroxylated microbiologically by means of Colletotrichum lini to 3beta,7alpha,15alpha-trihydroxy-5-androsten-17-one (XVIII), which is treated with acetone and boron trifluoride etherate yielding the acetonide (XIX). Hydrolysis of (XIX) with HCl in methanol affords the 3beta,7beta,15alpha-isomer (XX), which is also obtained from (XVIII) by isomerization with perchloric acid in methylisobutylketone. Selective acylation of (XX) with pivaloyl chloride affords the 3beta,15alpha-dipivaloyloxy compound (XXI), which is submitted to cyclopropanation with trimethylsulfoxonium iodide and NaOH as before yielding (IX).

参考文献中间体

合成目标

【1】 Losert, W.; Bittler, D.; Vasals-Stenzel, J.; Wiechert, R.; Kerb, U. (Schering AG); Novel spironolactones and process for their preparation. DE 2652761; US 4129564 .
【2】 Serradell, M.N.; Robinson, C.P.; Castaner, J.; Spirorenone. Drugs Fut 1985, 10, 6, 478.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	29663	1-(3-methoxyphenyl)acetone	3027-13-2	C₁₀H₁₂O₂	详情	详情
(IX)	29696	(4aR,4bS,6aS,7aS,8aS,8bS,8cR)-9-hydroxy-4a,6a-dimethyl-7-oxo-1,2,3,4,4a,4b,5,6,6a,7,7a,8,8a,8b,8c,9-hexadecahydrocyclopropa[4,5]cyclopenta[1,2-a]phenanthren-2-yl pivalate		C₂₅H₃₆O₄	详情	详情
(XVII)	29705	(8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one		C₁₉H₂₈O₂	详情	详情
(XVIII)	29702	(7S,8R,9S,10R,13S,14S,15S)-3,7,15-trihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one		C₁₉H₂₈O₄	详情	详情
(XIX)	29703	(2aS,5aS,10aR,10bS,12aS,12bS,12cR)-8-hydroxy-4,4,10a,12a-tetramethyl-2,2a,5a,7,8,9,10,10a,10b,11,12,12a,12b,12c-tetradecahydro-1H-benzo[h]indeno[1,7,6-def][1,3]benzodioxepin-1-one		C₂₂H₃₂O₄	详情	详情
(XX)	29706	(8R,9S,10R,13S,14S,15S)-3,7,15-trihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one		C₁₉H₂₈O₄	详情	详情
(XXI)	29704	(8R,9S,10R,13S,14S,15S)-15-[(2,2-dimethylpropanoyl)oxy]-7-hydroxy-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl pivalate		C₂₉H₄₄O₆	详情	详情

Extended Information