4-methyl-4-(phenylsulfanyl)-2-pentanone -Drug Synthesis Database

【结构式】

【分子编号】42267

【品名】4-methyl-4-(phenylsulfanyl)-2-pentanone

【CA登记号】

【分子式】C₁₂H₁₆OS

【分子量】208.32444

【元素组成】C 69.19% H 7.74% O 7.68% S 15.39%

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：(III)

Thiophenol (I) is treated with mesityl oxide (II) in CHCl3 and Et3N to yield derivative (III), which is then converted into alcohol (IV) by means of methylmagnesium iodide in Et2O. Cyclization of (IV) by means of AlCl3 in CS2 affords benzothiopyrane derivative (V) (1), which is nitrated by means of HNO3 and Ac2O or HOAc followed by treatment with Na2CO3 to provide (VI). Nitro derivative (VI) is then reduced with TiCl3 and HOAc or HCl and treated with NaOH to yield (VII). Amine (VII) is finally acylated with acid chloride (VIII) in benzene and pyridine.

参考文献中间体

合成目标

【1】 Spruce, L.W.; et al.; Novel heteroarotinoids: Synthesis and biological activity. J Med Chem 1991, 34, 1, 430.
【2】 Lu, S.; Zacheis, D.; Dhar, A.; et al.; Heteroarotinoids inhibit head and neck cancer cell lines in vitro and in vivo through both RAR and RXR retinoic acid receptors. J Med Chem 1999, 42, 21, 4434.
【3】 Nelson, E.C.; Madler, M.M.; Subramanian, S.; Birckbichler, P.J.; Berlin, K.D.; Patterson, M.K. Jr.; Benbrook, D.M. (Oklahoma State University); Heteroarotinoids - Anticancer agents with receptor specificity and TGASE activity. WO 9807716 .

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)	12951	Benzenethiol; Phenylmercaptan; Phenylhydrosulfide	108-98-5	C₆H₆S	详情	详情
(II)	42266	4-methyl-3-penten-2-one	141-79-7	C₆H₁₀O	详情	详情
(III)	42267	4-methyl-4-(phenylsulfanyl)-2-pentanone		C₁₂H₁₆OS	详情	详情
(IV)	42268	2,4-dimethyl-4-(phenylsulfanyl)-2-pentanol		C₁₃H₂₀OS	详情	详情
(V)	42269	2,2,4,4-tetramethylthiochromane		C₁₃H₁₈S	详情	详情
(VI)	42270	2,2,4,4-tetramethyl-6-nitrothiochromane		C₁₃H₁₇NO₂S	详情	详情
(VII)	42271	2,2,4,4-tetramethyl-6-thiochromanamine; 2,2,4,4-tetramethyl-3,4-dihydro-2H-thiochromen-6-ylamine		C₁₃H₁₉NS	详情	详情
(VIII)	42272	4-acetylbenzoyl chloride		C₉H₇ClO₂	详情	详情

Extended Information