CAS: 33815-57-5; (2R,3S,4S,4Ar,10Bs)-3,4-Dihydroxy-2-(Hydroxymethyl)-8,9,10-Trimethoxy-3,4,4A,10B-Tetrahydropyrano[3,2-C]Isochromen-6(2H)-One

英文名称(2R,3S,4S,4Ar,10Bs)-3,4-Dihydroxy-2-(Hydroxymethyl)-8,9,10-Trimethoxy-3,4,4A,10B-Tetrahydropyrano[3,2-C]Isochromen-6(2H)-One
中文名称二-O-甲基岩白菜素
IUPAC名称(2R,3S,4S,4aR,10bS)-3,4-dihydroxy-2-(hydroxymethyl)-8,9,10-trimethoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one
其它别名Di-O-Methylbergenin; Pyrano[3,2-C][2]Benzopyran-6(2H)-One, 3,4,4A,10B-Tetrahydro-3,4-Dihydroxy-2-(Hydroxymethyl)-8,9,10-Trimethoxy-, (2R,3S,4S,4Ar,10Bs)-; (2R,3S,4S,4Ar,10Bs)-3,4-Dihydroxy-2-(Hydroxymethyl)-8,9,10-Trimethoxy-3,4,4A,10B-Tetrahydropyrano[3,2-C]Isochromen-6(2H)-One; Tri-O-Methylnorbergenin; Di-O-Methylbergenin/dimethylbergenin
CAS编号33815-57-5
MFCD编号:MFCD20260365
分子式:C16H20O9分子量:356.33
产品CID: 1334822
产品分类天然产物 → 酚类

相似结构搜索
产品信息参考;;
InChIKey: RGHGUQJYNLPWPT-MUVVKYGDSA-N
InChI=1S/C16H20O9/c1-21-7-4-6-9(13(23-3)12(7)22-2)14-15(25-16(6)20)11(19)10(18)8(5-17)24-14/h4,8,10-11,14-15,17-19H,5H2,1-3H3/t8-,10-,11+,14+,15-/m1/s1
计算化学: 氢键受体数9.0氢键供体数3.0可旋转键数4.0

物理性质

熔点194-196 °C
沸点532.9±50.0 °C(预测)
闪点228.5±27.3 °C
密度1.417±0.06 g/cm3(预测)
pKa:12.74±0.60(预测)
PSA:123.91
LogP:-0.5946
溶解性Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
外观形态粉末
储存条件存储条件:2-8°C,干燥,密闭.

MSDS等安全信息

危险描述H303 May be harmful if swallowed+H313 Skin contact may be harmful+H333 Inhalation may be harmful to the body
防范说明P264+P280+P305+P351+P338+P337+P313
安全声明H303+H313+H333

上下游产品

diazomethane 11-O-(3',4',5'-trihydroxygalloyl)bergenin bergenin-4-O-gallate methanol

合成工艺路线路线简述

📜2-(2',3',4',6'-Tetra-O-Benzyl-β-D-Glucopyranosyl)-1-Trifluoromethanesulfonyloxy-3,4,5-Trimethoxybenzene置于palladium Diacetate 1,1'-双(二苯基膦)二茂铁,氯化亚砜,Palladium Hydroxide-Carbon,1,3-双(二苯基膦)丙烷,氢气,Potassium Acetate体系中,用甲醇,水,溶剂黄146,二甲基亚砜作为反应溶剂,化学反应 25.0H,反应生成二-O-甲基岩白菜素
参考文献:Short Total Synthesis Of 8,10-Di-O-Methylbergenin
标题:Short Total Synthesis Of 8,10-Di-O-Methylbergenin
摘要:A Short,High-Yielding Synthesis Of The C-Glucoside 8,10-Di-O-Methylbergenin Is Reported. Key Elements Of The Synthesis Are A Stereoselective Installation Of A Beta-C-Aryl Linkage,A Palladium(0)-Catalyzed Aryl Carbonylation,And A Regioselective Lactonization Reaction. This Pathway Should Allow Access To A Host Of Bergenin Analogues.
DOI:10.1021/ol026378E