pentanoic anhydride -Drug Synthesis Database

【结构式】

【分子编号】27683

【品名】pentanoic anhydride

【CA登记号】2082-59-9

【分子式】C₁₀H₁₈O₃

【分子量】186.25112

【元素组成】C 64.49% H 9.74% O 25.77%

与该中间体有关的原料药合成路线共 5 条

合成路线1 合成路线2 合成路线3 合成路线4 合成路线5

合成路线1

该中间体在本合成路线中的序号：(II)

This compound can be obtained in two different ways: 1) By reaction of phthalic anhydride (I) with valeric anhydride (II) in the presence of sodium valerate (A). 2) By reaction of 2-iodobenzoic acid (III) with copper propylacetylide (IV).

参考文献中间体

合成目标

【1】 Castro, C.E.; et al.; Indoles, benzofurans, phthalides and tolanes via copper (I) acetylides. J Org Chem 1966, 31, 12, 4071-78.
【2】 Lardelli, G.; et al.; A new gamma-lactone found in butter. Recl Trav Chim Pays-Bas 1966, 85, 43-55.
【3】 Castaner, J.; Blancafort, P.; Hillier, K.; Serradell, M.N.; Butylidenephthalide. Drugs Fut 1981, 6, 4, 216.

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)	31907	Sodium valerate; Sodium pentanoate		C₅H₉NaO₂	详情	详情
(I)	11900	2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride	85-44-9	C₈H₄O₃	详情	详情
(II)	27683	pentanoic anhydride	2082-59-9	C₁₀H₁₈O₃	详情	详情
(III)	37160	2-iodobenzoic acid	88-67-5	C₇H₅IO₂	详情	详情
(IV)	29069	1-pentynylcopper		C₅H₇Cu	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

By acylation of 9-(2-hydroxyethoxymethyl)guanine (I) with pentanoyl chloride (II) or pentanoyl anhydride (III).

参考文献中间体

合成目标

【1】 Beauchamp, L.M.; Krenitsky, T.A.; Acyclovir prodrugs: The road to valaciclovir. Drugs Fut 1993, 18, 7, 619.

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)	28279	2-amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one	59277-89-3	C₈H₁₁N₅O₃	详情	详情
(II)	15116	pentanoyl chloride; valeryl chloride	638-29-9	C₅H₉ClO	详情	详情
(III)	27683	pentanoic anhydride	2082-59-9	C₁₀H₁₈O₃	详情	详情

合成路线3

该中间体在本合成路线中的序号：(II)

The cyclization of 2-amino-5-iodobenzoic acid (I) with pentanoic anhydride (II) in basic medium gives 2-butyl-6-iodoquinazolin-4(3H)-one (III), which is condensed with CO and methanol by means of PdCl2(PPh3)2 and TEA yielding 2-butyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid methyl ester (IV). The Grignard condensation of (IV) with methylmagnesium bromide affords the tertiary alcohol (V), which is finally condensed with the tetrazolylbiphenyl (VI) by means of LiOMe, methylated at the tertiary alcohol with methyl iodide and NaH, and deprotected with NaOH in methanol/THF.

参考文献中间体

合成目标

【1】 Levin, J.I.; Chen, P.S.; Porter, R.S.; 2,3,6-Substituted quinazolinones as angiotensin II receptor antagonists. Drugs Fut 1995, 20, 1, 55.

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)	19964	5-Iodoanthranilic acid; 2-amino-5-iodobenzoic acid	5326-47-6	C₇H₆INO₂	详情	详情
(II)	27683	pentanoic anhydride	2082-59-9	C₁₀H₁₈O₃	详情	详情
(III)	41190	2-butyl-6-iodo-4(3H)-quinazolinone		C₁₂H₁₃IN₂O	详情	详情
(IV)	41191	methyl 2-butyl-4-oxo-3,4-dihydro-6-quinazolinecarboxylate		C₁₄H₁₆N₂O₃	详情	详情
(V)	41192	2-butyl-6-(1-hydroxy-1-methylethyl)-4(3H)-quinazolinone		C₁₅H₂₀N₂O₂	详情	详情
(VI)	15538	5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-trityl-2H-1,2,3,4-tetraazole	124750-51-2	C₃₃H₂₅BrN₄	详情	详情

合成路线4

该中间体在本合成路线中的序号：(II)

This compound can be obtained by several related ways: 1.- The cyclization of 3-aminothiophene-2-carboxamide (I) with pentanoyl anhydride (II) by means of DCC, DMAP and pyridine in DMF and NaOH gives 2-butylthieno[3,2-d]pyrimidin-4(3H)-one (III), which by reaction with POCl3 or SOCl2 affords 2-butyl-4-chlorothieno[3,2-d]pyrimidine (IV). Finally, this compound is condensed with cyclohexylamine (V) by means of triethylamine in in THF. 2.- The intermediate 2-butylthieno[3,2-d]pyrimidin-4-(3H)-one (III) can be obtained by other ways: a.- By cyclization of amide (I) with pentanoic acid (VI) by means of DCC, DMAP and pyridine in DMF and NaOH. b.- By cyclization of 3-aminothiophene-2-carboxylic acid methyl ester (VII) with pentanoic acid (VI) by means of DCC, DMAP and ammonia in dichloromethane. c.- By cyclization of 3-aminothiophene-2-carboxylic acid methyl ester (VII) with pentanoyl chloride (VIII) by means of pyridine and ammonia. d.- By cyclization of 3-aminothiophene-2-carboxylic acid (IX) with pentanoic anhydride (II) and ammonia.

参考文献中间体

合成目标

【1】 Crespo, M. I.; Pages, L.; Vega, A.; Segarra, V.; Lopez, M.; Domenech, T.; Miralpeix, M.; Beleta, J.; Ryder, H.; Palacios, J.M.; Design, synthesis, and biological activities of new thieno[3,2-d]pyrimidines as selective type 4 phosphodiesterase inhibitors. J Med Chem 1998, 41, 21, 4021.

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)	27682	3-amino-2-thiophenecarboxamide	147123-47-5	C₅H₆N₂OS	详情	详情
(II)	27683	pentanoic anhydride	2082-59-9	C₁₀H₁₈O₃	详情	详情
(III)	27684	2-butylthieno[3,2-d]pyrimidin-4(3H)-one		C₁₀H₁₂N₂OS	详情	详情
(IV)	27685	2-butyl-4-chlorothieno[3,2-d]pyrimidine		C₁₀H₁₁ClN₂S	详情	详情
(V)	17966	cyclohexanamine; cyclohexyl amine; cyclohexylamine	108-91-8	C₆H₁₃N	详情	详情
(VI)	19682	pentanoic acid	109-52-4	C₅H₁₀O₂	详情	详情
(VII)	27686	3-amino-2-thiophenecarboxylic acid methyl ester; methyl 3-amino-2-thiophenecarboxylate	22288-78-4	C₆H₇NO₂S	详情	详情
(VIII)	15116	pentanoyl chloride; valeryl chloride	638-29-9	C₅H₉ClO	详情	详情
(IX)	27687	3-amino-2-thiophenecarboxylic acid		C₅H₅NO₂S	详情	详情

合成路线5

该中间体在本合成路线中的序号：(II)

Ftalic anhydride (I) id treated with butyric anhydride (II) and sodium butyrate to obtain lactone (IV), which is hydrogenated to target compound by means H2 Nickel Raney.

参考文献中间体

合成目标

【1】 Fang, H.J.; Chen, Y.W.; Sun, S.W.; Hu, Q.; Yang, J.S.; Studies on chemical constituents of volatile oil from Apium graveolens seeds. Chin Drug Analyt J 1984, 4, 205.
【2】 Chen, Y.W.; Yang, J.S.; Isolation and determination of active components of Apium graveolens. Chin Pharm Bull 1984, 19, 670.
【3】 Wang, X.-W.; 3-n-Butylphthalide. Drugs Fut 2000, 25, 1, 16.

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)	11900	2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride	85-44-9	C₈H₄O₃	详情	详情
(II)	27683	pentanoic anhydride	2082-59-9	C₁₀H₁₈O₃	详情	详情
(III)	31907	Sodium valerate; Sodium pentanoate		C₅H₉NaO₂	详情	详情
(IV)	31908	3-[(Z)butylidene]-2-benzofuran-1-one	551-08-6	C₁₂H₁₂O₂	详情	详情

Extended Information