nonanoyl chloride -Drug Synthesis Database

【结构式】

【分子编号】30296

【品名】nonanoyl chloride

【CA登记号】764-85-2

【分子式】C₉H₁₇ClO

【分子量】176.68608

【元素组成】C 61.18% H 9.7% Cl 20.07% O 9.06%

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：(XX)

Ketone (XVI) was treated with phenylselanyl chloride and LHMDS yielding the selenium derivative (XVII). Enone (XVIII) was then produced by oxidative elimination of the selenide (XVII). Reduction of the unsaturated ketone (XVIII) with NaBH4 in the presence of CeCl3 gave the 3-beta-allylic alcohol (XIX). This was acylated with nonanoyl chloride (XX) to afford ester (XXI). Finally, acid deprotection of the silyl ether and the p-methoxyphenyl acetal of (XXI) furnished the title compound.

参考文献中间体

合成目标

【1】 Winkler, J.D.; Lewin, N.E.; Blumberg, P.M.; Harrison, S.; Kim, S.; Synthesis and biological evaluation of highly functionalized analogues of ingenol. J Am Chem Soc 1999, 121, 2, 296.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XVI)	30290	(1S,5S,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-7-(4-methoxyphenyl)-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadec-10-ene-4,17-dione		C₃₉H₄₄O₆Si	详情	详情
(XVII)	30291	(1S,5S,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-7-(4-methoxyphenyl)-3-(phenylselanyl)-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadec-10-ene-4,17-dione		C₄₅H₄₈O₆SeSi	详情	详情
(XVIII)	30292	(1S,5S,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-7-(4-methoxyphenyl)-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadeca-2,10-diene-4,17-dione		C₃₉H₄₂O₆Si	详情	详情
(XIX)	30293	(1S,4S,5R,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-4-hydroxy-7-(4-methoxyphenyl)-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadeca-2,10-dien-17-one		C₃₉H₄₄O₆Si	详情	详情
(XX)	30296	nonanoyl chloride	764-85-2	C₉H₁₇ClO	详情	详情
(XXI)	30297	(1S,4S,5S,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-7-(4-methoxyphenyl)-17-oxo-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadeca-2,10-dien-4-yl nonanoate		C₄₈H₆₀O₇Si	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Friedel-Crafts acylation of phenol (I) with nonanoyl chloride (II) in the presence of AlCl3 afforded ketone (III). Aminosulfonyl chloride (V) was prepared by decarboxylation of chlorosulfonyl isocyanate (IV) upon treatment with formic acid. Finally, condensation of the sodium phenolate of (III) with aminosulfonyl chloride (V) furnished the title sulfamate.

参考文献中间体

合成目标

【1】 Ahmed, S.; et al.; Novel inhibitors of the enzyme estrone sulfatase (ES). Bioorg Med Chem Lett 2001, 11, 6, 841.
【2】 Ahmed, S.; James, K.; Owen, C.P.; Patel, C.K.; Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES). J Steroid Biochem Mol Biol 2002, 80, 4-5, 419.
【3】 Ahmed, S. (Kingston University); Sulphamate cpds.. WO 0104086 .

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)	23540	Phenol	108-95-2	C₆H₆O	详情	详情
(II)	30296	nonanoyl chloride	764-85-2	C₉H₁₇ClO	详情	详情
(III)	50915	4-n-Nonanoylphenol; 4-Hydroxynonanophenone	14392-69-9	C₁₅H₂₂O₂	详情	详情
(IV)	14101	Chlorosulfonyl isocyanate	1189-71-5	CClNO₃S	详情	详情
(V)	40598	amidosulfonoyl chloride	7778-42-9	H₂ClNO₂S	详情	详情

Extended Information