Triphenylphosphine → ethyl (2Z)-2-[(1R,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl]oxyimino-3-oxobutanoate

HRID 1194901

반응식

HRID 1194901 반응식
[CH3:1][C@@H:2]1[CH2:7][C@H:6]([OH:8])[C@@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O/[N:32]=[C:33](/[C:39](=[O:41])[CH3:40])\[C:34]([O:36][CH2:37][CH3:38])=[O:35].N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH3:1][C@@H:2]1[CH2:7][C@@H:6]([O:8]/[N:32]=[C:33](/[C:39](=[O:41])[CH3:40])\[C:34]([O:36][CH2:37][CH3:38])=[O:35])[C@@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 165675(+)-MentholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178472876HCID 178472876, 화합물

생성물 1

HCID 177701097ethyl (2Z)-2-[(1R,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl]oxyimino-3-oxobutanoate수율 14%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(1S, 2R, 5S)-(+)-Menthol (7.03 g, 45 mmol), triphenylphosphine (8.65 g, 33 mmol), ethyl (Z)-2-hydroxyimino-3-oxobutyrate (4.77 g, 33 mmol) and diethyl azodicarboxylate (5.7 g, 33 mmol) were reacted by analogy with Example 4a Method 3 to give the title compound (1.37 g, 14%), νmax (CH2Cl2) 2960, 2930, 2870, 1745, 1690, 1370, 1320, 1235, 1075, and 1010cm-1 ; δH (400 MHz, CDCl3) 0.87 (3H, d, J 6.6 Hz), 0.90 (3H, d, J 6.8 Hz), 0.92 (3H, d, J 6.7 Hz), ca 0.9 (1H, m), 1.02-1.12 (2H, m), 1.1-1.3 (1H, m), 1.32 (3H, t, J 7.1 Hz), 1.50-1.65 (2H, m), 1.67-1.78 (2H, m), 2.06-2.18 (1H, m), 2.40 (1H, s), 4.34 (2H, dq, J 7.1 and 1.0 Hz), and 4.70 (1H, broad s); δ13C (100 MHz, CDCl3), 14.24 (CH3), 20.70 (CH3), 20.97 (CH3), 22.26 (CH3) 25.04 (CH2), 25.11 (CH3) 26.06 (CH), 29.10 (CH), 34.77 (CH2), 39.44 (CH2) 46.98 (CH), 61.70 (CH2), 83.43 (CH), 150.28, 161.53, 192.94 [Ammonia CI mass spectrum Found: MH+ (298); MNH+ (315)].

출처 및 근거

ORD 기록
ord-ff99fa30d5ed4ace9bfa212ac8548c65
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04816452

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