4-heptanol -Drug Synthesis Database

【结构式】

【分子编号】34880

【品名】4-heptanol

【CA登记号】589-55-9

【分子式】C₇H₁₆O

【分子量】116.20344

【元素组成】C 72.35% H 13.88% O 13.77%

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：(I)

This compound has been obtained by two different ways: 1) The reaction of dipropylcarbinol (I) with HBr gives 4-bromoheptane (II), which is treated with KCN to yield 2-propylpentanenitrile (III). Finally, this compound is hydrolyzed to the target compound with NaOH or with H2SO4. 2) The condensation of cyanacetic acid ethyl ester (IV) with propyl bromide (V) by means of sodium propoxide in propanol gives crude dipropylcyanaacetic acid ethyl ester, which, without isolation, is hydrolyzed with NaOH in hot water yielding dipropylcyanacetic acid (VI). The decarboxylation of (VI) at 140-190 C affords the previously reported 2-propylpentanenitrile (III).

参考文献中间体

合成目标

【1】 Walles, M.; et al.; Z Physiolog Chem 1947, 282, 2, 137.
【2】 Grain, C.; Chignac, M.; Pigerol, C. (Labaz); Process for the preparation of acetonitrile deriv.. US 4155929 .
【3】 Chignac, M.; Grain, C.; Pigerol, C. (Labaz); Process for preparing an acetonitrile deriv.. GB 1522450 .
【4】 Pigerol, C.; Grain, C.; Chignac, M. (Labaz); Process for preparing acetic acid derivs.. GB 1529786 .

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)	34880	4-heptanol	589-55-9	C₇H₁₆O	详情	详情
(II)	34881	4-bromoheptane	998-93-6	C₇H₁₅Br	详情	详情
(III)	34882	2-propylpentanenitrile	13310-75-3	C₈H₁₅N	详情	详情
(IV)	11877	Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate	105-56-6	C₅H₇NO₂	详情	详情
(V)	28721	1-bromobutane	109-65-9	C₄H₉Br	详情	详情
(VI)	34883	2-cyano-2-propylpentanoic acid		C₉H₁₅NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXI)

The reaction of 3,4-dihydro-1H-2-benzopyran (VII) with benzoyl chloride and ZnCl2 gives benzoic acid 2-[2-(chloromethyl)phenyl]ethyl ester (XIII), which is condensed with hexamethylenetetramine (XIV) yielding the amminium salt (XV). The hydrolysis of (XV) affords 2-(2-benzoyloxyethyl) benzaldehyde (XVI), which is condensed with nitromethane as before to give the nitrostyrene (XVII). The cyclization of (XVII) with FeCl3 and acetyl chloride as before yields 4-(2-benzoyloxyethyl)-3-chloroindolin-2-one (XVIII), which is dechlorinated with hydrazine and Pd/C to the indolinone (XIX). The hydrolysis of (XIX) with NaOH affords 4-(2-hydroxyethyl)indolin-2-one (XX), which is acylated with TsCl giving the tosylate (XXI). Finally, this compound is condensed with dipropylamine (II).

参考文献中间体

合成目标

【1】 Hayler, J.D.; et al.; Development of large-scale syntheses or ropinirole in the pursuit of a manufacturing process. Org Process Res Dev 1998, 2, 1, 3.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
	19273	acetyl chloride	75-36-5	C₂H₃ClO	详情	详情
	39563	nitromethane	75-52-5	CH₃NO₂	详情	详情
(II)	21856	N,N-dipropylamine; N-propyl-1-propanamine	142-84-7	C₆H₁₅N	详情	详情
(VII)	34866	3,4-dihydro-1H-isochromene	493-05-0	C₉H₁₀O	详情	详情
(XIII)	34872	2-(chloromethyl)phenethyl benzoate		C₁₆H₁₅ClO₂	详情	详情
(XIV)	34873	1,3,5,7-tetraazatricyclo[3.3.1.1(3,7)]decane	100-97-0	C₆H₁₂N₄	详情	详情
(XV)	34874	1-[2-[2-(benzoyloxy)ethyl]benzyl]-3,5,7-triaza-1-azoniatricyclo[3.3.1.1(3,7)]decane chloride		C₂₂H₂₇ClN₄O₂	详情	详情
(XVI)	34875	2-formylphenethyl benzoate		C₁₆H₁₄O₃	详情	详情
(XVII)	34876	2-[(E)-2-nitroethenyl]phenethyl benzoate		C₁₇H₁₅NO₄	详情	详情
(XVIII)	34877	2-(3-chloro-2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl benzoate		C₁₇H₁₄ClNO₃	详情	详情
(XIX)	34878	2-(2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl benzoate		C₁₇H₁₅NO₃	详情	详情
(XX)	34879	4-(2-Hydroxyethyl)indolin-2-one	139122-19-3	C₁₀H₁₁NO₂	详情	详情
(XXI)	34880	4-heptanol	589-55-9	C₇H₁₆O	详情	详情

Extended Information