(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol -Drug Synthesis Database

【结构式】

【分子编号】21965

【品名】(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol

【CA登记号】4602-84-0

【分子式】C₁₅H₂₆O

【分子量】222.37084

【元素组成】C 81.02% H 11.79% O 7.19%

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：(III)

The reacion of 1-(4-chlorobenzoyl)-2-methyl-5-methoxyindolyl-3-acetic acid (I) with SOCl2 in refluxing benzene gives the corresponding acyl chloride (II), which is condensed with farnesol (III) by means of triethylamine in THF.

参考文献中间体

合成目标

【1】 Yamatsu, I.; Abe, S.; Inai, Y.; Suzuki, T.; Kinoshita, K.; Mishima, M.; Katoh, Y.; Kobayashi, S.; Murakami, M.; Yamada, K. (Eisai Co., Ltd.); Polyprenyl esters of acemethacins and anti-inflammatory method of use thereof. DE 3226687; FR 2510107; GB 2104513; JP 8315940 .
【2】 Serradell, M.N.; Castaner, J.; E-0710. Drugs Fut 1984, 9, 7, 506.

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)	22930	2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid		C₁₉H₁₆ClNO₄	详情	详情
(II)	24047	2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl chloride		C₁₉H₁₅Cl₂NO₃	详情	详情
(III)	21965	(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol	4602-84-0	C₁₅H₂₆O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VIII)

Pentafluoronitrobenzene (I) was reacted with NaNO2 in DMSO to give phenol (II), which was then protected as the allyl ether (IV) upon treatment with allyl bromide (III) and Na2CO3 in refluxing acetone. Further displacement of one fluorine atom of (III) with NaOH under phase transfer conditions afforded phenol (V). This was then attached to a solid phase carboxypolystyrene resin using diisopropyl carbodiimide (DIC) in the presence of pyridine and DMAP. Deprotection of the allyl ether from the resulting resin ester (VI) was accomplished with sodium p-toluenesulfinate and palladium catalyst to yield phenol (VII). The Mitsunobu etherification of phenol (VII) with farnesol (VIII) furnished farnesyl ether (IX). The final product was then cleaved from the resin by treatment with NaOMe in MeOH-THF.

参考文献中间体

合成目标

【1】 Huang, L.-J.; Chang, F.C.; Lee, K.H.; Wang, J.P; Teng, C.M.; Kuo, S.C.; Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of substituted 3-chloro-5,8-dimethoxy-1,4-naphthoquinone and related compounds. Bioorg Med Chem 1998, 6, 12, 2261.

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)	21958	1,2,3,4,5-pentafluoro-6-nitrobenzene	880-78-4	C₆F₅NO₂	详情	详情
(II)	21959	2,3,5,6-tetrafluoro-4-nitrophenol		C₆HF₄NO₃	详情	详情
(IV)	21961	allyl 2,3,5,6-tetrafluoro-4-nitrophenyl ether; 1-(allyloxy)-2,3,5,6-tetrafluoro-4-nitrobenzene		C₉H₅F₄NO₃	详情	详情
(V)	21962	3-(allyloxy)-2,4,5-trifluoro-6-nitrophenol		C₉H₆F₃NO₄	详情	详情
(VI)	21963	3-(allyloxy)-2,4,5-trifluoro-6-nitrophenyl 4-hydroxybenzoate		C₁₆H₁₀F₃NO₆	详情	详情
(VIII)	21965	(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol	4602-84-0	C₁₅H₂₆O	详情	详情
(IX)	21966	2,4,5-trifluoro-6-nitro-3-[[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]oxy]phenyl 4-hydroxybenzoate		C₂₈H₃₀F₃NO₆	详情	详情

Extended Information