Benzylideneacetone → HCID 66895711, 화합물

HRID 322590

반응식

HRID 322590 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:9]([NH2:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1.[C:12]1(/[CH:18]=[CH:19]/[C:20](=O)[CH3:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:23]([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:23][C@H:20]([CH:19]=[CH:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:21][NH:11][C@@H:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:10]

참가 물질

5

반응물 3

HCID 637759BenzylideneacetoneHCID 5003444Sodium cyanoborohydrideHCID 7020759(R)-1-(3-Methoxyphenyl)ethylamine

생성물 1

HCID 66895711HCID 66895711, 화합물

시약·촉매·용매 1

HCID 11026Titanium isopropoxide촉매

실험 절차

In a similar fashion, an equal molar amount of (R)-1-(3-methoxyphenyl)ethylamine, trans-4-phenyl-3-butene-2-one and 1.25 molar equivalents titanium(IV) isopropoxide were mixed 4 hr at rt and the intermediate imine treated with an ethanolic sodium cyanoborohydride (5 ml of 1 M, 5 mmol). Work-up and chromatography afforded (R,R)-N-(2-methyl-4-phenybut-3-enyl)-1-(3-methoxyphenyl)ethylamine, 25H, as an oil; m/z (rel. int.) 283 (M+, 4), 268 (13), 178 (40), 135 (100), 105 (15), 91 (47), 77 (13) and (S,R)-N-(2-methyl-4-phenybut-3-enyl)-1-(3-methoxyphenyl)ethylamine, 25I, as an oil; m/z (rel. int.) 283 (M+, 4), 268 (13), 178 (40), 135 (100), 105 (15), 91 (47), 77 (13).

출처 및 근거

ORD 기록
ord-b4b7d2b0696847ca96eca99c0b5a736c
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211244B1

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