Nitrogen → HCID 131735722, 화합물

HRID 2201739노트

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HRID 2201739 반응식
N#N.[CH3:3][C:4]([CH3:22])([O:6][C@H:7]1[C@@:15]2([CH3:16])[C@@H:10]([CH2:11][C:12]([OH:21])=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:14]2)[CH2:9][CH2:8]1)[CH3:5].[CH2:23]=[CH:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30]>C(Cl)Cl>[CH3:5][C:4]([CH3:22])([O:6][C@H:7]1[C@@:15]2([CH3:16])[C@@H:10]([CH2:11][C:12](=[O:21])[C:13]([CH2:23][CH2:24][C:25](=[O:31])[CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])([C:17]([O:19][CH3:20])=[O:18])[CH2:14]2)[CH2:9][CH2:8]1)[CH3:3]

참가 물질

5

반응물 3

HCID 947NitrogenHCID 118047521,7-Octadien-3-oneHCID 131735723HCID 131735723, 화합물

생성물 1

HCID 131735722HCID 131735722, 화합물수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
180 °C

실험 절차

Neutral alumina (15 g) was heated in a flask at 180° C. under high vacuum for 4 h. After cooling down to room temperature, the flask was filled with N2. Compound 31 (7.2 g, 25.5 mmol), 1,7-octadien-3-one (4.3 g, 30 mmol), and CH2Cl2 (30 mL) were added to the anhydrous alumina at room temperature. The mixture was stirred at room temperature for 16 h. The suspension was filtered through Celite® 545 which was washed with CH2Cl2 (100 mL×3). The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes) to afford compound 32 (9.4 g, 91%). The compound is a mixture of diastereomers at position C-5 in a 3 to 1 ratio. The major diastereomer had: 1H NMR (CDCl3) δ 5.72-5.60 (m, 1H), 4.95-4.86 (m, 2H), 3.64 (s, 3H), 3.35 (t, J=7.1 Hz, 1H), 1.05 (s, 9H), 0.75 (s, 3H); 13C NMR (CDCl3) δ 209.5, 208.0, 173.7, 137.8, 115.0, 79.9, 72.4, 56.2, 52.2, 46.9, 45.5, 42.4, 42.1, 41.7, 38.1, 32.9, 31.3, 30.5, 28.6, 28.4, 25.5, 22.6; IR νmax 1714, 1641, 1435 cm−1. Anal. Calcd for (C24H38O5): C, 70.90; H, 9.42. Found: C, 71.16; H, 9.70.

후처리

  1. temperatureAfter cooling down to room temperature
  2. filtrationThe suspension was filtered through Celite® 545 which
  3. washwas washed with CH2Cl2 (100 mL×3)
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-1d0793dc58c448d3b0be44769a0f3fc1
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365502B2

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