Trichloroacetic Acid → 2-(1-Trichloroacetyloxy-4-methyl-3-pentenyl)-5,8-dihydroxy-1,4-naphthoquinone

HRID 1939719

반응식

HRID 1939719 반응식
[CH3:1][C:2]([CH3:21])=[CH:3][CH2:4][C@@H:5]([OH:20])[C:6]1[C:16](=[O:17])[C:15]2[C:14]([OH:18])=[CH:13][CH:12]=[C:11]([OH:19])[C:10]=2[C:8](=[O:9])[CH:7]=1.C1(N=C=NC2CCCCC2)CCCCC1.[Cl:37][C:38]([Cl:43])([Cl:42])[C:39](O)=[O:40]>CN(C)C1C=CN=CC=1.ClCCl>[Cl:37][C:38]([Cl:43])([Cl:42])[C:39]([O:20][CH:5]([C:6]1[C:16](=[O:17])[C:15]2[C:10]([C:8](=[O:9])[CH:7]=1)=[C:11]([OH:19])[CH:12]=[CH:13][C:14]=2[OH:18])[CH2:4][CH:3]=[C:2]([CH3:21])[CH3:1])=[O:40]

참가 물질

6

반응물 3

HCID 6421Trichloroacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 479503Shikonin

생성물 1

HCID 214680832-(1-Trichloroacetyloxy-4-methyl-3-pentenyl)-5,8-dihydroxy-1,4-naphthoquinone수율 92%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

288 mg (1 mmole) of shikonin, 226 mg (1.1 mmole) of dicyclohexylcarbodiimide and 30 mg (0.25 mmole) of 4-dimethylaminopyridine were dissolved in 3 ml of dry dichloromethane. To the resulting solution was added 163 mg (1 mmole) of trichloroacetic acid at 0° C. under nitrogen gas, and the mixture was stirred for 30 minutes and then at room temperature for further 3 hours. The resulting product was separated and purified according to the procedures as described in Example 1 to obtain 398 mg (Yield: 92%) of the title compound having the following structure as a red precipitate.

후처리

  1. waitat room temperature for further 3 hours
  2. customThe resulting product was separated
  3. custompurified

출처 및 근거

ORD 기록
ord-8c7a4a74a1c24f1b9817b52afb94797d
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05696276

연결된 노트

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