Hexanoic Acid → 2-(1-n-Hexanoyloxy-4-methyl-3-pentenyl)-5,8-dihydroxy-1,4-naphthoquinone

HRID 1939722

反応式

HRID 1939722 の反応式
[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.[C:37](O)(=[O:43])[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>CN(C)C1C=CN=CC=1.ClCCl>[C:37]([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:43])[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

参加物

6

反応物 3

HCID 8892Hexanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 479503Shikonin

生成物 1

HCID 214680742-(1-n-Hexanoyloxy-4-methyl-3-pentenyl)-5,8-dihydroxy-1,4-naphthoquinone収率 39%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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 116 mg (1 mmole) of n-hexanoic 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 150 mg (Yield: 39%) of the title compound having the following structure as a red precipitate.

後処理

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

出典と根拠

ORDレコード
ord-8ad3d0a7c0eb41f1bb9e76155fa30496
出典データセット
uspto-grants-1997_12
特許番号
US05696276

関連ノート

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