(2S,3R,4R,4aS,10bR)-3,4,8,9,10-五羟基-2-(羟基甲基)-3,4,4a,10b-四氢-2H-吡喃并[3,2-c]异苯并吡喃-6-酮 | 79595-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2S,3R,4R,4aS,10bR)-3,4,8,9,10-五羟基-2-(羟基甲基)-3,4,4a,10b-四氢-2H-吡喃并[3,2-c]异苯并吡喃-6-酮
• 英文名称: norbergenin
• 英文别名: Norbergenin；(2R,3S,4S,4aR,10bS)-3,4,8,9,10-pentahydroxy-2-(hydroxymethyl)-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
• CAS: 79595-97-4
• 化学式: C₁₃H₁₄O₉
• 分子量: 314.249
• InChiKey: GDYGAIKPBLFCKR-OIPGZRGRSA-N

物化性质

• 熔点：
  248-249 °C
• 沸点：
  705.9±60.0 °C(Predicted)
• 密度：
  1.799±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,4aS,10bR)-3,4,8,9,10-五羟基-2-(羟基甲基)-3,4,4a,10b-四氢-2H-吡喃并[3,2-c]异苯并吡喃-6-酮 在 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 72.0h， 生成 Hexanoic acid (6aS,7S,7aR,11aR,12aS)-1,2,3-tris-benzyloxy-9-(4-methoxy-phenyl)-5-oxo-6a,7,7a,11,11a,12a-hexahydro-5H-6,8,10,12-tetraoxa-benzo[a]anthracen-7-yl ester
  参考文献：
  名称：

  Synthesis and neuroprotective activity of bergenin derivatives with antioxidant activity

  摘要：

  Norbergenin, which is the O-demethyl derivative of bergenin, the main component of Mallotus japonicus, has been found to show moderate antioxidant activity (IC50 13 muM in DPPH radical scavenging; 32 muM in superoxide anion scavenging). Modification of sugar part on norbergenin by coupling with a variety of fatty acids was employed for increasing its antioxidant activity. Selective esterification of hydroxyl groups on the sugar part enhanced greatly antioxidant activity. The most potent one is norbergenin 11-caproate, which not only exhibits stronger antioxidant activity than that of catechin but also prevents neuronal death at 10 muM on the primary culture of rat cortical neurons in DM EM supplemented with N2. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00666-1
• 作为产物：
  描述：

  岩白菜素 在 sodium dithionite 、 水 作用下， 以 水 、 丙酮 为溶剂， 以69%的产率得到(2S,3R,4R,4aS,10bR)-3,4,8,9,10-五羟基-2-(羟基甲基)-3,4,4a,10b-四氢-2H-吡喃并[3,2-c]异苯并吡喃-6-酮
  参考文献：
  名称：

  Hypervalent iodine-mediated oxygenative phenol dearomatization reactions

  摘要：

  Both lambda(3)- and lambda(5)-iodanes have proven to be useful reagents in the oxygenative dearomatization of phenols, and exploitations of their chemistry in the conception of both substrate- and reagent-controlled asymmetric variants of such a transformation of great value for natural product synthesis have shown evident signs of success. Moreover, the use of stabilized IBX (i.e., SIBX) in our methodology for O-demethylation of 2-methoxyphenols, which relies on the same key oxygenating dearomatization event, is reported here to be much more efficacious than that of 1BX itself in the chemoselective one-step conversion of homovanillyl alcohol into hydroxytyrosol, and bergenin into norbergenin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.078

文献信息

• Tchitchibabine et al., Bulletin de la Societe Chimique de France, <hi>1936</hi>, vol. <5> 3, p. 2343,2346
  作者：Tchitchibabine et al.

  DOI：——

  日期：——