Water → Chlorin

HRID 1190763

반응식

[CH2:1]1[C:5]2=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[N:17]=[C:16]([CH:18]=[C:19]5[NH:24][C:22](=[CH:23][C:3](=[N:4]2)[CH2:2]1)[CH:21]=[CH:20]5)[CH2:15][CH2:14]4)=[CH:9][CH:8]=3.O>>[CH2:9]1[C:10]2=[CH:12][C:13]3[NH:17][C:16]([CH:18]=[C:19]4[N:24]=[C:22]([CH:23]=[C:3]5[NH:4][C:5](=[CH:6][C:7](=[N:11]2)[CH2:8]1)[CH:1]=[CH:2]5)[CH:21]=[CH:20]4)=[CH:15][CH:14]=3

참가 물질

반응물 2

HCID 962Water

HCID 9548778Bacteriochlorin

생성물 1

HCID 65106Chlorin

실험 절차

Method B (from 16): Following the procedure described for the preparation of 6, treatment of 16 (40.0 mg, 0.0705 mmol, 1.0 equiv) with FeCl36.H2O (66.3 mg, 4.0 equiv) resulted in the desired product. Purification was done by flash column chromatography (silica gel, 3% acetone in CH2Cl2). Yield: 25.2 mg, 55%. 1H NMR (400 MHz, CDCl3) δ: 9.18 (s, 1H, 10-H), 9.03 (d, J=14 Hz, 1H, 5-H), 8.65 (s, 1H, 20-H), 5.79-5.86 (m, 1H, 31-H), 5.48 (d, 2H, 132-H), 4.41-4.50 (m, 1H, 8-H), 4.20-4.22 (m, 1H, 7-H), 3.90 (t, J=8.0 Hz, 2H, 17-CH2), 3.75 (s, 3H, COOCH3), 3.52-3.66 (m, 5H, 31-OCH2+12-CH3), 3.43 (d, J=3.6 Hz, 3H, 2-CH3), 3.23 (s, 3H, 18-CH3), 2.94 (t, J=8.0 Hz, 2H, 171-CH2), 2.42-2.52 (m, 1H, 81-H), 2.13-2.20 (m, 1H, 81-H), 2.10 (d, J=6.8 Hz, 3H, 31-CH3), 1.91/1.87 (d, J=7.2 Hz, 3H, 7-CH3), 1.66-1.76 (m, 3H, 31-OCH2CH2CH2CH2CH2CH3), 1.15-1.23 (m, 9H, 31-OCH2CH2CH2CH2CH2CH3+81-CH3), 0.78-0.81 (m, 3H, 31-OCH2CH2CH2CH2CH2CH3), −0.34 (br s, 1H, NH), −1.52 (br s, 1H, NH). MS (ESI) m/z: 651.4 (M++1). UV-vis, CH2Cl2, λmax nm (ε): 669 (4.45×104), 612 (6.77×103), 540 (6.77×103), 513 (1.11×104), 411 (7.82×104).

출처 및 근거

ORD 기록: ord-ca78a36cbcdc43d1a6a4372e95112f9f
출처 데이터셋: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08679459B2

연결된 노트

불러오는 중…