butyl nitrite -Drug Synthesis Database

【结构式】

【分子编号】31340

【品名】butyl nitrite

【CA登记号】544-16-1

【分子式】C₄H₉NO₂

【分子量】103.121

【元素组成】C 46.59% H 8.8% N 13.58% O 31.03%

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：(II)

The oxidation of acetone (I) with butyl nitrite (II) with a catalytic amount of HCl gives methylglyoxal 1-oxime (III), which is then condensed with aminoguanidine (IV) in hot water acidified with HCl.

参考文献中间体

合成目标

【1】 Nagaki, D.; Nishimura, T.; Hasegawa, K.; Toku, H.; Sakaguchi, H.; Yamazaki, C.; Antiviral compounds. IX. Synthesis and anti-influenza virus activity of bis-amidinohydrazones of glyoxal and methylglyoxal. Kitasato Arch Exp Med 1975, 48, 4, 171-181.
【2】 Serradell, M.N.; Eastland, G.W.; Castaner, J.; Mitoguazone. Drugs Fut 1984, 9, 3, 199.

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)	23199	2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one； Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether	67-64-1	C₃H₆O	详情	详情
(II)	31340	butyl nitrite	544-16-1	C₄H₉NO₂	详情	详情
(III)	30362	2-oxopropanal oxime	306-44-5	C₃H₅NO₂	详情	详情
(IV)	10015	1-Hydrazinecarboximidamide; Hydrazinecarboximidamide	79-17-4	CH₆N₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：

Nitrosation of 5,6-dimethoxy-1-indanone (I) with n-butyl nitrite and HCl in MeOH at 40 C provided oxime (II). Subsequent catalytic hydrogenation of ketone and oxime groups of (II) afforded the 2-aminoindan (III). Reductive alkylation of (III) using propionic acid and NaBH4 then gave the target dipropylamino compound, which was isolated as the hydrochloride salt after separation of some unreacted material by treatment with phenyl isocyanate.

参考文献中间体

合成目标

【1】 Cannon, J.G.; et al.; Conformationally restricted congeners of dopamine derived from 2-aminoindan. J Med Chem 1982, 25, 12, 1442.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	20178	propionic acid	79-09-4	C₃H₆O₂	详情	详情
	31340	butyl nitrite	544-16-1	C₄H₉NO₂	详情	详情
(I)	13430	5,6-Dimethoxy-1-indanone; 2,3-Dihydro-5,6-dimethoxy-1H-inden-1-one	2107-69-9	C₁₁H₁₂O₃	详情	详情
(II)	27302	5,6-dimethoxy-1H-indene-1,2(3H)-dione 2-oxime		C₁₁H₁₁NO₄	详情	详情
(III)	27303	5,6-dimethoxy-2,3-dihydro-1H-inden-2-ylamine		C₁₁H₁₅NO₂	详情	详情

Extended Information