isogemichalcone B | 376362-05-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: isogemichalcone B
• 英文别名: Demethoxyisogemichalcone C；[(E)-4-[3-[(E)-3-(2,4-dihydroxyphenyl)prop-2-enoyl]-2,6-dihydroxyphenyl]-2-methylbut-2-enyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 376362-05-9
• 化学式: C₂₉H₂₆O₈
• 分子量: 502.521
• InChiKey: XXQUTHYOIGFGPG-MPKNGZDBSA-N

物化性质

• 沸点：
  797.4±60.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-(2-hydroxy-4-(methoxymethoxy)-3-methylphenyl)ethanone 在 盐酸 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 三苯胂 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 三苯基膦 、 potassium hydroxide 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 为溶剂， 反应 182.0h， 生成 isogemichalcone B
  参考文献：
  名称：

  The synthetic preparation of naturally-occurring aromatase inhibitors, morachalcone A, isogemichalcone B, and isogemichalcone C

  摘要：

  A convergent synthesis applicable to the preparation of oxidized prenylchalcones is reported that relies on key Claisen-Schmidt, Mitsunobu, and vinyl/benzyl Stille coupling operations. The synthetic strategy was applied towards the preparation of the natural products morachalcone A and isogemichalcones B & C, allowing their preparation in less than 10 steps and 6-8% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.068

文献信息

• The synthetic preparation of naturally-occurring aromatase inhibitors, morachalcone A, isogemichalcone B, and isogemichalcone C
  作者：Drew R. Brandt、Kristina M. Pannone、Joseph J. Romano、Eduard G. Casillas

  DOI：10.1016/j.tet.2013.09.068

  日期：2013.11

  A convergent synthesis applicable to the preparation of oxidized prenylchalcones is reported that relies on key Claisen-Schmidt, Mitsunobu, and vinyl/benzyl Stille coupling operations. The synthetic strategy was applied towards the preparation of the natural products morachalcone A and isogemichalcones B & C, allowing their preparation in less than 10 steps and 6-8% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.